synthesis, antibacterial, antifungal and dft studies on

* Corresponding author: Adole, Vishnu Ashok

E-mail: [email protected] © 2021 by SPC (Sami Publishing Company)

Advanced Journal of Chemistry-Section A Theoretical, Engineering and Applied Chemistry

Journal homepage: www.ajchem-a.com

Original Research Article

Synthesis, Antibacterial, Antifungal and DFT Studies on Structural, Electronic and Chemical Reactivity of (E)-7-((1H-Indol-3-yl)methylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Vishnu Ashok Adole *

PG Department of Chemistry, Mahatma Gandhi Vidyamandir’s Arts, Science and Commerce College, Manmad, Taluka-Nandgaon, District- Nashik, India-423104

A R T I C L E I N F O

A B S T R A C T

Article history

Submitted: 20 March 2021

Revised: 09 April 2021

Accepted: 18 April 2021

Available online: 19 April 2021

Manuscript ID: AJCA-2103-1250

DOI: 10.22034/AJCA.2021.278047.1250

The present study deals with the theoretical investigation of structural, molecular, electronic, and chemical reactivity details of (E)-7-((1H-indol-3-yl)methylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (ITHF). The ITHF molecule is characterized by proton nuclear magnetic resonance (1H NMR) and carbon nuclear magnetic resonance (13C NMR) spectral techniques. The Becke-3-Lee-Yang-Parr functional (B3LYP) level of theory at the 6-311G(d,p) basis set was used for the density functional theory (DFT) investigation. Bond lengths were predicted from the optimized molecular structure, and the physical and chemical properties of the molecules were inferred as a consequence. The HOMO and LUMO are computed and their energies were established. The calculated HOMO-LUMO energy gap is 3.67 eV indicating inevitable electron transfer phenomenon within the ITHF molecule. Amongst all carbon atoms, the C6 carbon as more positive and C21 as more negative carbon atoms. The molecular electrostatic surface potential revealed that the negative electrostatic potential is present over oxygen atoms and the positive, on the other hand, is located over two aromatic rings' hydrogen atoms in the ITHF molecule. Importantly, the ITHF compound were evaluated for antibacterial activities against two Gram positive bacteria namely Bacillus subtilis and Staphylococcus aureus and two Gram negative bacteria namely Escherichia coli and Proteus vulgaris and two fungal agents namely Aspergillus niger and Candida albicans. The ITHF compound was found to show good antimicrobial action.

K E Y W O R D S

6-311G(d,p)

Computational

FMO

Antimicrobial

MESP

Advanced Journal of Chemistry-Section A, 2021, 4(3), 175-187

mailto:[email protected]

https://orcid.org/0000-0001-7691-7884

V. A. Adole / Adv. J. Chem. A, 2021, 4(3), 175-187

176

Introduction

Indole is a privileged s heterocyclic framework

in view of its incorporation with proteins as

amino acid tryptophan. Indole is a planar bicyclic

compound with a benzene and pyrrole ring fused

together. Since medicinal compounds have an

indole center, they are a special heterocyclic

structure with a wide variety of biological

properties [1-4]. The astonishing biological

properties of heterocyclic compounds containing

indole nucleus are antimicrobial [5],

antitubercular [6], anticonvulsant [7], anti-

inflammatory [8], analgesic [9], anticancer [10],

insecticidal activity [11], antioxidant [12],

antiviral [13], antidepressant [14], and

antihistaminic [15]. Likewise, indanones appear

to be a most promising lead for drug

development [16-20].

Theoretical chemistry has advanced and DFT

calculations are considered as valuable tool for

predicting the structural, electronic, and spectral

properties of the molecules [21-24]. Importantly,

DFT computations offer a wealth of knowledge

about the molecules' spectroscopic and quantum

chemical parameters, allowing researchers to

investigate their chemical behaviour [25-31].

DFT techniques have also been used to study UV-

visible, NMR, and Raman spectroscopic

examinations [32-34]. Theoretical calculations

G R A P H I C A L A B S T R A C T


177

using DFT has been used to asses various

structural, molecular and spectral properties 2,3-

dihydrobenzofuran derivatives [35], 5,6-

diaroylisoindoline-1,3-dione [36] , morphonium

formate and acetate Ionic liquid salts [37] 2,3-

dihydrobenzofuran linked indanones [38], 2-(3-

bromophenyl)-4-(4-bromophenyl)-2,3-dihydro-

1H-1,5-benzodiazepine [39], (E)-3-(4-

chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-

one [40], ethyl 4-(4-isopropylphenyl)-6-methyl-

2-oxo-1,2,3,4-tetrahydropyrimidine-5-

carboxylate [41], 5-(4-chlorophenyl)-3-(3,4-

dimethoxyphenyl)-1-phenyl-4,5-dihydro-1H-

pyrzole [42], (E)-1-(2,3-

dihydrobenzo[b][1,4]dioxin-6-yl)-3-(3,4,5-

trimethoxyphenyl)prop-2-en-1one [43],

dihydropyrimidinones [44], (2E)-3-(2,6-

dichlorophenyl)-1-(4-fluoro)-prop-2-en-1-one

[45], and ethyl-4-(3,4-dimethoxyphenyl)-6-

methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-

carboxylate [46]. The efficient synthesis methods

were found to speed up the rate of reaction and

thereby follow the principles of green chemistry

[47-53].

The DFT method with the B3LYP functional is

proved to be one of the best computational

strategies to predict molecular properties [54-

62]. Using the B3LYP functional with a 6-

311G(d,p) basis set, the great deal of agreement

between theoretical and experimental results can

be obtained [21, 22]. In light of all of the above, I

would like to present a DFT analysis on the

structural, mechanical, and chemical reactivity of

(E)-7-((1H-indol-3-yl)methylene)-1,2,6,7-

tetrahydro-8H-indeno[5,4-b]furan-8-one in this

paper. The usefulness of DFT on molecular

structure, bond length, bond angle, and Mulliken

atomic charges has been explored in the flow

study. The DFT technique was used to analyse

essential parameters such as total energy,

HOMO-LUMO energies, charge distribution,

thermodynamic properties, and so on. This is the

first article on the synthesis and DFT

investigation of the title compound.

Experimental

General Remarks

The high-purity chemicals were purchased from

the Sigma laboratory in Nashik. The chemicals

were used exactly as they were obtained, with no

further purification needed. The melting point

was measured in an uncorrected open capillary

system. A sophisticated multinuclear FT NMR

Spectrometer model Advance-II (Bruker) was

used to record 1H and 13C NMR spectra with a 1H

frequency of 500 MHz and 13C frequency 126

MHz using DMSO-d6 as solvent. The reaction was

monitored by thin-layer chromatography using

aluminium sheets with silica gel 60 F254

(Merck).

Experimental Procedure for the Synthesis ITHF

A mixture of 1,2,6,7-tetrahydro-8H-indeno[5,4-

b]furan-8-one (8 mmol) and 1H-indole-3-

carbaldehyde (10 mmol) was mixed in 5 mL

ethanol taken in a conical flask. To this mixture 2

mL 20 % NaOH was added. The resulting alkaline

mixture was stirred on a magnetic stirrer at

room temperature until the formation of the

desired product (checked by TLC). The crude

product was transferred into a beaker containing

crushed ice, stirred, acidified by dilute HCl

filtered, dried naturally, and recrystallized using

hot ethanol to furnish pure yellow solid (Scheme

1).


178

Scheme 1. Synthesis of ITHF molecule

Computational Details

The Gaussian 03 W programme was used to

perform all calculations [63]. DFT method with

B3LYP functional was used for the theoretical

simulations [64]. The title compound's geometry

optimization and corresponding energy were

determined using a 6-311G(d,p) base set and C1

point group symmetry. As a result, the optimum

geometrical parameters, energy, atomic charges,

dipole moment, were theoretically determined.

In light of the optimised structure, the Mulliken

atomic charges, molecular electrostatic potential

surface, electronic properties such as HOMO–

LUMO energies, and dipole moment were also

investigated.

Antimicrobial Screening

The agar diffusion method was used to access

the antimicrobial activities [65].

Chloramphenicol was used as a standard for

antibacterial evaluation and Amphotericin-B for

antifungal screening. The antibacterial screening

was performed against Escherichia coli, Proteus

vulgaris, Staphylococcus aureus and Bacillus

subtilis while the antifungal screening was

performed against Aspergillus niger, and Candida

albicans.

Results and Discussion

Spectral Analysis of ITHF

The 1H NMR spectrum predicts the types and

total number of hydrogen atoms in the molecule.

There are total of ten types of protons in the title

molecule and therefore has furnished ten signals

in the 1H NMR spectrum. The NH group signal is

located at 12.05 δ as broad singlet. The two

proton present in benzene ring are ortho coupled

with J = 7.1 Hz. All other signals are correctly

matched with the structure of the ITHF molecule.

The 13C NMR spectrum predicts types of carbons

atoms in the molecule and therefore one can

anticipate the skeleton of the molecule. There are

total of 20 types of carbons that have displayed

20 signals in the 13C NMR spectrum affirming the

structure. The signal at 193.23 δ is due to the

carbonyl carbon of ketone group.

Spectral Data of the ITHF

1H NMR (500 MHz, DMSO) δ 12.05 (s, 1H), 7.97

(m, 1H), 7.87 (d, J = 7.7 Hz, 1H), 7.84 (d, J = 2.1

Hz, 1H), 7.51 – 7.48 (m, 1H), 7.36 (d, J = 8.1 Hz,

1H), 7.24 – 7.20 (m, 1H), 7.08 (d, J = 8.1 Hz, 1H),

4.63 (t, J = 8.8 Hz, 2H), 3.91 – 3.87 (m, 2H), 3.46

(t, J = 8.8 Hz, 2H). 13C NMR (126 MHz, DMSO) δ

193.23, 160.35, 141.10, 136.58, 135.59, 130.95,

129.35, 127.95, 125.73, 124.92, 124.31, 123.07,

121.14, 118.63, 114.98, 112.67, 112.10, 72.34,

32.72, 28.42.

Computational study

Molecular Structure Study

Figure 1 shows the optimised molecular

structure of the title molecule. Figure 2 illustrates

the geometrical viewpoints around various

dimensions (A, B, and C Cartesian axes). The

optimised molecular geometry reveals a lot

about the spatial orientation of different atoms in

a molecule. From optimized molecular

structures, it tends to be handily observed that

the ITHF molecule possesses C1 point group


179

Figure 1. Optimized molecular structure of ITHF molecule

A B

C

Figure 2. Molecular structures of ITHF molecule along Cartesian axes

symmetry due to the overall asymmetry of the

molecule. Moreover, it is additionally apparent

that it contains a non-planar dihydrofuran ring.

The non-planarity of dihydrofuran can be

ascribed to the CH2 group (adjacent to an oxygen

atom) which is either above or beneath the plane.


180

It can likewise be seen that the remaining

skeleton is in immaculate planar position and

hence can have broadened conjugation. This data

is a lot of value for the assurance of different

spectroscopic elements. The optimized

geometrical parameters bond lengths and bond

angles are presented in Table 1 and Table 2

respectively. The longest and the shortest

aromatic (benzene ring) double bonds are C33-

C37 (1.4072 Å) and C29-C37 (1.3869 Å)

respectively. The C16-O20 bond length is 1.2207

Å and the C21-C22 is 1.3489 Å. The N35-H36 is

1.0064 Å C24-C28 is 1.452 Å, C24-C25 is 1.3864

Å, and C27-C28 is 1.4155 Å. Other bond length

data are also having great agreement with the

structure of the title compound. The bond angle

of C2-C1-C6 is 118.5673°, N35-C27-C37 is

167.6792°, C25-N35-H36 is 124.8482°, C27-N35-

H36 is 125.3017°, C27-C37-C29 is 61.6042°, and

C27-C37-C33 is 59.6078°. Similar to bond

lengths, bond angles are also in great agreement.

Table 1. Optimized bond length data of ITHF molecule by DFT/ B3LYP with 6-311G(d,p) basis set

Bond lengths (Å)

C1-C2 1.3995 C17-H19 1.098

C1-C6 1.3938 C17-C21 1.512

C1-H7 1.083 C21-C22 1.3489

C2-C3 1.3911 C22-H23 1.0882

C2-H8 1.0851 C22-C24 1.4399

C3-C4 1.403 C24-C25 1.3864

C3-C17 1.5182 C24-C28 1.452

C4-C5 1.3876 C25-H26 1.0768

C4-C16 1.4832 C25-N35 1.3701

C5-C6 1.3922 C27-C28 1.4155

C5-C9 1.5073 C27-C31 1.3957

C6-O15 1.3631 C27-N35 1.3836

C9-H10 1.0948 C28-C29 1.4021

C9-H11 1.0907 C29-H30 1.084

C9-C12 1.5464 C29-C37 1.3869

C12-H13 1.0941 C31-H32 1.0844

C12-H14 1.0894 C31-C33 1.3873

C12-O15 1.4577 C33-H34 1.0839

C16-O20 1.2207 C33-C37 1.4072

C16-C21 1.4901 N35-H36 1.0064

C17-H18 1.098 C37-H38 1.0838


181

Table 2.Optimized bond angle data of ITHF molecule by DFT/ B3LYP with 6-311G(d,p) basis set

Bond Angles (°)

C2-C1-C6 118.5673 H13-C12-O15 107.5001 C31-C27-H38 61.6271

C2-C1-H7 121.3799 H14-C12-O15 107.3392 N35-C27-C37 167.6792

C6-C1-H7 120.0528 C6-O15-C12 107.2649 N35-C27-H38 168.0208

C1 -C2 -C3 119.9549 C4-C16-C20 126.6805 C24-C28-C27 107.4531

C1-C2-H8 119.3584 C4-C16-C21 106.1319 C24-C28-C29 133.7828

C3-C2-H8 120.6859 C20-C16-C21 127.1875 C24-C28-H38 154.996

C2-C3-C4 120.2934 C3-C17-H18 111.5069 C27-C28-C29 118.7641

C2-C3-C17 128.96 C3-C17-H19 111.4606 C29-C28-H38 21.2132

C4-C3-C17 110.7464 C3-C17-H21 103.6253 C28-C29-H30 120.6995

C3-C4-C5 120.4689 H18-C17-H19 106.758 H30-C29-C37 120.3352

C3-C4-C16 110.0855 H18-C17-C21 111.7852 C27-C31-H32 121.514

C5-C4-C16 129.4445 H19-C17-C21 111.8102 C27-C31-C33 117.2802

C4-C5-C6 118.3685 C16-C21-C17 109.4108 H32-C31-C33 121.2059

C4-C5-C9 133.0982 C16-C21-22 120.6638 C31-C33-H34 119.4336

C6-C5-C9 108.4745 C17-C21-C22 129.9254 C31-C33-C37 121.1434

C1-C6-C5 122.345 C21-C22-H23 114.2765 H34-C33-C37 119.4231

C1-C6-O15 124.3887 C21-C22-C24 129.8936 C25-N-35-C27 109.85

C5-C6-C15 113.265 H23-C22-C24 115.8299 C25-N35-H36 124.8482

C5-C9-H10 110.6161 C22-C24-C25 129.2666 C27-N35-H36 125.3017

C5-C9-H11 113.0881 C22-C24-C28 124.9501 C27-C37-C29 61.6042

C5-C9-C12 101.1004 C25-C24-C28 105.7833 C27-C37-C33 59.6078

H10-C9-H11 107.0815 C24-C25-H26 129.934 C28-C37-C33 90.5111

C10-C9-C12 112.2447 C24-C25-N35 109.9007 C29-C37-C33 121.212

H11-C9-C12 112.7689 H26-C25-N35 120.1653 C29-C37-H38 119.6058

C9-C12-H13 111.5569 C28-C27-C31 122.635 C33-C37-H38 119.1822

C9-C12-H14 114.0455 C28-C27-N35 107.0129 - -

C9-C12-O15 106.9839 C31-C27-N35 130.3521 - -

H1-C12-H14 109.1082 C31-C27-C37 61.9687 - -

Mulliken Charge Study

Mulliken nuclear charges are computed

employing electron density. The charge

distribution on molecules plays a crucial role in

quantum mechanical computations for molecular

structures. Figure 3 displays a pictorial


182

representation of the ITHF molecule's Mulliken

atomic charges as calculated by the DFT/B3LYP

strategy with a 6-311G(d,p) base collection,

which are tabulated in Table 3. According to

Mulliken atomic charges, all hydrogen atoms

have a net positive charge, but the H36 hydrogen

atom, with an atomic charge of 0.231206, is

extremely electropositive. This can be explained

by the presence of a nitrogen atom. Of all carbon

atoms, the C6 atom has the largest net positive

charge (0.238011), while the C21 atom has the

highest net negative charge (-0.223465).

Figure 3. Mulliken atomic charges of ITHF molecule

Table 3. Mulliken atomic charges of ITHF molecule

Atom Charge Atom Charge

1 C -0.067941 20 O -0.331903

2 C -0.072073 21 C -0.223465

3 C -0.139505 22 C 0.030134

4 C -0.030881 23 H 0.102743

5 C -0.151155 24 C -0.121282

6 C 0.238011 25 C 0.142017

7 H 0.102130 26 H 0.108385

8 H 0.078968 27 C 0.192375

9 C -0.166374 28 C -0.111941

10 H 0.139746 29 C -0.055485

11 H 0.143308 30 H 0.095022

12 C -0.012196 31 C -0.039770

13 H 0.120070 32 H 0.087005

14 H 0.120365 33 C -0.102738

15 O -0.357419 34 H 0.093166

16 C 0.226458 35 N -0.441363

17 C -0.086756 36 H 0.231206

18 H 0.134046 37 C -0.100405

19 H 0.134094 38 H 0.093401


183

Molecular Electrostatic Surface Potential (MESP)

Study

The MESP plot of ITHF is shown in Figure 4.

The MESP guide can be used to relate any

molecule's properties such as dipole moment,

electronegativity, partial charges, and chemical

reactivity. The molecular electrostatic potential

is the total charge distribution of a molecule

space. Different coloured areas reflect positive,

negative, and neutral potentials. It can be shown

that negative electrostatic potential occurs over

oxygen atoms in this situation. The positive

electrostatic potential, on the other hand, is

located over two aromatic rings' hydrogen

atoms. The zones with varying electrostatic

potential are likely to provide important

knowledge about multiple types of

intermolecular interactions, allowing one to

predict the molecule's chemical behaviour.

Figure 4. Molecular electrostatic surface potential of ITHF molecule

Frontier Molecular Orbital Study

The HOMO-LUMO analysis is often used to

forecast the most receptive condition in -electron

frameworks and to describe a few forms of

conjugated mechanism responses [66-71]. A

smaller HOMO-LUMO energy difference indicates

a weaker molecule, while a large gap indicates a

harder molecule. The knowledge about charge

transfer within the molecule can be envisioned

using the frontier molecular orbital (FMO)

investigation. Figure 5 depicts the ITHF

molecule's maximum inhabited molecular orbital

(HOMO) and lowest unoccupied molecular

orbital (LUMO). The bioactive property of the

molecule is based on the charge transfer

phenomenon. The FMO thesis elucidates the

molecule's reactivity, and the active site can be

determined by the distribution of frontier

orbitals. The HOMO and LUMO parameters are

important in the analysis of quantum chemical

parameters. The HOMO-LUMO analysis is often

used to forecast the most receptive condition in

electron frameworks and to describe a few forms

of conjugated mechanism responses. A smaller

HOMO-LUMO energy difference indicates a

weaker molecule, while a large gap indicates a

harder molecule. In ITHF, the HOMO-LUMO

energy difference is 3.67 eV.


184

Figure 5. HOMO-LUMO pictures of ITHF molecule

Antimicrobial Screening Study

The antibacterial activity of the synthesised

compound ITHF was examined on two

Gram positive and two Gram negative bacteria,

while the antifungal activity was tested on two

fungal species. Table 4 summarises the findings

of the antimicrobial evaluation. According to the

observations, the ITHF is a mild antimicrobial

agent against the strains examined. The findings

have showed that ITHF is a more antibacterial

than antifungal agent, with stronger antibacterial

activity than antifungal activity. The ITHF has

not been found to be successful against

Staphylococcus aureus Gram strain among the

strains examined. The ITHF compound has been

identified to be a more effective antibacterial

agent than an antifungal agent. The antimicrobial

information provided here may indeed be a good

approach for further antimicrobial agent

research.

Table 4. Zone of inhibition shown by ITHF against four bacterial and two fungal agents

Entry E. coli P. vulgaris S. aureus B. subtilis A. niger C. albicans

ITHG ++ ++ _ ++ - +

Chloramphenicol +++++ +++++ +++++ +++++ NA NA

Amphotericin-B NA NA NA NA ++++ ++++

+ = < 5 mm zone, ++ = 5-10 mm zone, +++ = >10-15 mm zone, ++++ = >15-20 mm, +++++ = > 20 mm, - = No inhibition, NA = Not applicable

Conclusions

In summary, the present investigation covers

the synthesis, antibacterial, antifungal, and

computational aspects of (E)-7-((1H-indol-3-

yl)methylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-

b]furan-8-one. The 1H NMR and 13C NMR spectral

techniques were used to affirm the structure of

the titled compound. The DFT examination used

the Becke-3-Lee-Yang-Parr functional (B3LYP)

level of theory at the 6-311G(d,p) basis set. The

ITHF molecule has C1 point group symmetry.

The optimized geometrical parameters bond

lengths and bond angles are also described. All

hydrogen atoms have a net positive charge, the

C6 atom has the highest net positive charge and

the C21 atom has the highest net negative charge

in the titled compound. It can be seen from MESP

that, negative electrostatic potential exists over

oxygen atoms. The HOMO-LUMO energy gap in

ITHF is 3.67 eV. The antimicrobial screening

against bacterial and fungal strains revealed here


185

that the ITHF compound is a more effective

antibacterial agent than an antifungal agent.

Acknowledgement

The author acknowledges the central

instrumentation facility (CIF), Savitribai Phule

Pune University, Pune for the spectral analysis.

The author is very much thankful to Prin. Dr. B.S.

Jagdale for providing necessary research

facilities. The author is grateful to Professor Dr.

A. B. Sawant and Professor Dr. T.B. Pawar for the

Gaussian study. Dr. Aapoorva P. Hiray

Coordinator, M. G. Vidyamandir institute is

gratefully acknowledged for the Gaussian

package.

Disclosure statement

No potential conflict of interest was reported by

the author.

ORCID

Vishnu Ashok Adole : 0000-0001-7691-7884

References

[1] S. Biswal, U. Sahoo, S. Sethy, H.K.S. Kumar, M.

Banerjee, Asian J. Pharm. Clin. Res., 2012, 5, 1–

6. [Google Scholar], [Publisher]

[2] N.K. Kaushik, N. Kaushik, P. Attri, N. Kumar,

C.H. Kim, A.K. Verma, E.H. Choi, Molecules,

2013, 18, 6620–6662. [CrossRef], [Google

Scholar], [Publisher]

[3] Y. Wan, Y. Li, C. Yan, M. Yan, Z. Tang, Eur. J.

Med. Chem., 2019, 183, 111691. [CrossRef],

[Google Scholar], [Publisher]

[4] T.V Sravanthi. S.L. Manju, Eur. J. Pharm. Sci.,

2016, 91, 1–10. [CrossRef], [Google Scholar],

[Publisher]

[5] M. Sayed, A.M. Kamal El-Dean, M. Ahmed, R.

Hassanien, Synth. Commun., 2018, 48, 413–

421. [CrossRef], [Google Scholar], [Publisher]

[6] S.V. Karthikeyan, S. Perumal, K.A. Shetty, P.

Yogeeswari, D. Sriram, Bioorganic Med. Chem.

Lett., 2009, 19, 3006–3009. [CrossRef],


[7] P. Ahuja, N. Siddiqui, Eur. J. Med. Chem., 2014,

80, 509–522. [CrossRef], [Google Scholar],

[Publisher]

[8] A.S.H. da Silva Guerra, D.J. do Nascimento

Malta, L.P.M. Laranjeira, M.B.S. Colaço, N.C.

Maia, M.D.C.A. de Lima, S.L. Galdino, I. da

Rocha Pitta, T. Gonçalves-Silva, Int.

Immunopharmacol., 2011, 11, 1816–1822.

[CrossRef], [Google Scholar], [Publisher]

[9] M.A. Radwan, E.A. Ragab, N.M. Sabry, S.M., El-

Shenawy, Bioorg. Med. Chem., 2007, 15, 3832–


[10] J. Singh Sidhu, R. Singla, V. Jaitak, Anticancer

Agents Med. Chem., 2016, 16, 160–173.


[11] H. Hayashi, K. Takiuchi, S. Murao, M. Arai,

Agricultural and biological chemistry, 1989,

53, 461–469. [CrossRef], [Google Scholar],

[Publisher]

[12] M.S. Estevão, L.C. Carvalho, D. Ribeiro, D.

Couto, M. Freitas, A. Gomes, L.M. Ferreira, E.

Fernandes, M.M.B. Marques, Eur. J. Med. Chem.,

2010, 45, 4869–4878. [CrossRef], [Google


[13] M.Z. Zhang, Q. Chen, G.F. Yang, Eur. J. Med.

Chem., 2015, 89, 421–441. [CrossRef], [Google


[14] P.O. Patil, S.B. Bari, Arab. J. Chem., 2016, 9,

588–595. [CrossRef], [Google Scholar],

[Publisher]

[15] M. Ajitha, K. Rajnarayana, M. Sarangapani,

Pharmazie, 2002, 57, 796–799. [Google

Scholar]

[16] V.A. Adole, T.B. Pawar, B.S. Jagdale, J. Chin.

Chem. Soc., 2020, 67, 306–315. [CrossRef],


[17] P. Rajagopalan, K.A. Alahmari, A.A.

Elbessoumy, M. Balasubramaniam, R. Suresh,

M.E.A. Shariff, H.C. Chandramoorthy, Cancer

Chemother. Pharmacol., 2016, 77, 393–404.


https://orcid.org/0000-0001-7691-7884

https://orcid.org/0000-0001-7691-7884

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=S.+Biswal%2C+U.+Sahoo%2C+S.+Sethy%2C+H.K.S.+Kumar%2C+M.+Banerjee%2C+Asian+J.+Pharm.+Clin.+Res.%2C+2012%2C+5%2C+1-6&btnG=

https://www.researchgate.net/profile/Sabyasachi-Biswal/publication/283857931_Indole_The_molecule_of_diverse_biological_activities/links/5f699006a6fdcc00863431ac/Indole-The-molecule-of-diverse-biological-activities.pdf

https://doi.org/10.3390/molecules18066620

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=N.K.+Kaushik%2C+N.+Kaushik%2C+P.+Attri%2C+N.+Kumar%2C+C.H.+Kim%2C+A.K.+Verma%2C+E.H.+Choi%2C+++Molecules%2C+2013%2C+18%2C+6620-6662.&btnG=

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=N.K.+Kaushik%2C+N.+Kaushik%2C+P.+Attri%2C+N.+Kumar%2C+C.H.+Kim%2C+A.K.+Verma%2C+E.H.+Choi%2C+++Molecules%2C+2013%2C+18%2C+6620-6662.&btnG=

https://www.mdpi.com/1420-3049/18/6/6620

https://doi.org/10.1016/j.ejmech.2019.111691

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=Y.+Wan%2C+Y.+Li%2C+C.+Yan%2C+M.+Yan%2C+Z.+Tang%2C+Eur.+J.+Med.+Chem.%2C+2019.+183%2C+111691%2C+Indole%3A+A+privileged+scaffold+for+the+design+of+anti-cancer+agents.&btnG=

https://www.sciencedirect.com/science/article/abs/pii/S0223523419308414

https://doi.org/10.1016/j.ejps.2016.05.025

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=T.V+Sravanthi.+S.L.+Manju%2C+Eur.+J.+Pharm.+Sci.%2C+2016.+91%2C+1-10.Indoles%E2%80%94a+promising+scaffold+for+drug+development&btnG=

https://www.sciencedirect.com/science/article/abs/pii/S092809871630207X

https://doi.org/10.1080/00397911.2017.1403627

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.+Sayed%2C+A.M.+Kamal+El-Dean%2C+M.+Ahmed%2C+R.+Hassanien%2C+Synth.+Commun.%2C+2018%2C+48%2C+413-421.&btnG=

https://www.tandfonline.com/doi/abs/10.1080/00397911.2017.1403627

https://doi.org/10.1016/j.bmcl.2009.04.029

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=S.V.+Karthikeyan%2C+S.+Perumal%2C+K.A.+Shetty%2C+P.+Yogeeswari%2C+D.+Sriram%2C+Bioorganic+Med.+Chem.+Lett.%2C+2009.+19%2C+3006-3009.&btnG=

https://www.sciencedirect.com/science/article/abs/pii/S0960894X09005447

https://doi.org/10.1016/j.ejmech.2014.04.043

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=P.+Ahuja%2C+N.+Siddiqui%2C+Eur.+J.+Med.+Chem.%2C+2014%2C+80%2C+509-522.Anticonvulsant+evaluation+of+clubbed+indole-1%2C+2%2C+4-triazine+derivatives%3A+A+synthetic+approach&btnG=


https://doi.org/10.1016/j.intimp.2011.07.010

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=Gon%C3%A7alves-Silva%2C++Int.+Immunopharmacol.%2C+2011%2C+11%2C1816-1822%2C+Anti-inflammatory+and+antinociceptive+activities+of+indole%E2%80%93imidazolidine+derivatives&btnG=

https://www.sciencedirect.com/science/article/pii/S1567576911002876

https://doi.org/10.1016/j.bmc.2007.03.024

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.A.+Radwan%2C+E.A.+Ragab%2C+N.M.+Sabry%2C+S.M.%2C+El-Shenawy%2C+Bioorg.+Med.+Chem.%2C+2007%2C+15%2C+3832-3841.+&btnG=


https://doi.org/10.2174/1871520615666150520144217

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=J.+Singh+Sidhu%2C+R.+Singla%2C+V.+Jaitak%2C+Anticancer+Agents+Med.+Chem.%2C+2016%2C+16%282%29%2C+160-173%2C+Indole+derivatives+as+anticancer+agents+for+breast+cancer+therapy%3A+a+review&btnG=

https://www.ingentaconnect.com/content/ben/acamc/2016/00000016/00000002/art00004

https://doi.org/10.1080/00021369.1989.10869287

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=H.+Hayashi%2C+K.+Takiuchi%2C+S.+Murao%2C+M.+Arai%2C++Agricultural+and+biological+chemistry%2C+1989%2C+53%2C+461-469&btnG=



https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.S.+Estev%C3%A3o%2C+L.C.+Carvalho%2C+D.+Ribeiro%2C+D.+Couto%2C+M.+Freitas%2C+A.+Gomes%2C+L.M.+Ferreira%2C+E.+Fernandes%2C+M.M.B.+Marques%2C++Eur.+J.+Med.+Chem.%2C+2010%2C+45%2C+4869-4878.+&btnG=

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.S.+Estev%C3%A3o%2C+L.C.+Carvalho%2C+D.+Ribeiro%2C+D.+Couto%2C+M.+Freitas%2C+A.+Gomes%2C+L.M.+Ferreira%2C+E.+Fernandes%2C+M.M.B.+Marques%2C++Eur.+J.+Med.+Chem.%2C+2010%2C+45%2C+4869-4878.+&btnG=



https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.Z.+Zhang%2C+Q.+Chen%2C+G.F.+Yang%2C+Eur.+J.+Med.+Chem.%2C+2015%2C+89%2C+421-441&btnG=

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.Z.+Zhang%2C+Q.+Chen%2C+G.F.+Yang%2C+Eur.+J.+Med.+Chem.%2C+2015%2C+89%2C+421-441&btnG=


https://doi.org/10.1016/j.arabjc.2013.08.027

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=P.O.+Patil%2C+S.B.+Bari%2C+Arab.+J.+Chem.%2C+2016%2C+9%284%29%2C+588-595%2C+Synthesis%2C+characterization+and+screening+for+antidepressant+and+anticonvulsant+activity+of+4%2C+5-dihydropyrazole+bearing+indole+derivatives&btnG=

https://www.sciencedirect.com/science/article/pii/S1878535213003079

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.+Ajitha%2C+K.+Rajnarayana%2C+M.+Sarangapani%2C+Pharmazie%2C+2002%2C+57%2C+796-799&btnG=

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.+Ajitha%2C+K.+Rajnarayana%2C+M.+Sarangapani%2C+Pharmazie%2C+2002%2C+57%2C+796-799&btnG=

https://doi.org/10.1002/jccs.201900015

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=V.A.+Adole%2C+T.B.+Pawar%2C+B.S.+Jagdale%2C+J.+Chin.+Chem.+Soc.%2C+2020%2C+67%2C+306-315&btnG=

https://onlinelibrary.wiley.com/doi/abs/10.1002/jccs.201900015

https://doi.org/10.1007/s00280-015-2956-8

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=P.+Rajagopalan%2C+K.A.+Alahmari%2C+A.A.+Elbessoumy%2C+M.+Balasubramaniam%2C+R.+Suresh%2C++M.E.A.+Shariff%2C+H.C.+Chandramoorthy%2C+Cancer+Chemother.+Pharmacol.%2C+2016%2C+77%2C+393-404&btnG=

https://link.springer.com/article/10.1007%2Fs00280-015-2956-8


186

[18] J.C. Menezes, RSC adv., 2017, 7, 9357–9372.


[19] M. Turek, D. Szczęsna, M. Koprowski, P.

Bałczewski, Beilstein J. Org. Chem., 2017, 13,


[Publisher]

[20] P. Rajagopalan, H.C. Chandramoorthy, Asian

Biomed., 2020, 13, 131–139. [CrossRef],


[21] V.A. Adole, T.B. Pawar, B.S. Jagdale, J. Sulphur

Chem., 2021, 42, 131–148. [CrossRef], [Google


[22] V.A. Adole, R.H. Waghchaure, S.S. Pathade,

M.R. Patil, T.B. Pawar, B.S. Jagdale, Mol. Simul.,

2020, 46, 1045–1054. [CrossRef], [Google


[23] S.L. Dhonnar, V.A. Adole, N.V. Sadgir, B.S.

Jagdale, Phys. Chem. Res., 2021, 9, 193–209.


[24] S.S. Pathade, B.S. Jagdale, Phys. Chem. Res.,

2020, 8, 671–687. [CrossRef], [Google


[25] M. Shkir, S. AlFaify, H. Abbas, S. Muhammad,

Spectrochim. Acta A, 2015, 147, 84–92.


[26] A. Srivastava, R. Mishra, S. Kumar, K. Dev, P.

Tandon, R. Maurya, J. Mol. Struct., 2015, 1084,


[Publisher]

[27] P. Manjusha, S. Muthu, B.R. Raajaraman, J.

Mol. Struct., 2020, 1203, p.127394. [CrossRef],


[28] A. Kumer, M.J. Islam, S. Paul, Chem.

Methodol., 2020, 4, 595–604. [CrossRef],


[29] A. Kumer, N. Sarker, S. Paul, A. Zannat, Adv. J.

Chem. A, 2019, 2, 190–202. [Google Scholar],

[Publisher]

[30] A. Kumer, M.N. Sarker, P.A.U.L. Sunanda, Int.

J. Chem. Technol., 2019, 3, 26–37. [CrossRef],


[31] M.J. Islam, A. Kumer, N. Sarker, S. Paul, A.

Zannat, Adv. J. Chem. A, 2019, 2, 316–326.


[32] J.R. Hidalgo, A. Neske, M.A. Iramain, P.E.

Alvarez, P.L. Bongiorno, S.A. Brandán, J. Mol.

Struct., 2019, 1196, 508–517. [CrossRef],


[33] M. Raja, R.R. Muhamed, S. Muthu, M. Suresh,

J. Mol. Struct., 2017, 1141, 284–298.


[34] M.A. Iramain, L. Davies, S.A. Brandán, J. Mol.

Struct., 2018, 1158, 245–254. [CrossRef],


[35] A. Nath, A. Kumer, M.W. Khan, J. Mol. Struct.,

2021, 1224, 129225. [CrossRef], [Google


[36] M.M. Hoque, M.S. Hussen, A. Kumer, M.W.

Khan, Mol. Simul., 2020, 46, 1298–1307.


[37] A. Kumer, M.N. Sarker, S. Paul, Turkish Comp.

Theo. Chem., 2019, 3, 59–68. [CrossRef],


[38] R.A. Shinde, V.A. Adole, B.S. Jagdale, T.B.

Pawar, B.S. Desale, R.S. Shinde, Mat. Sci. Res.

India, 2020, 17, 146–161. [CrossRef], [Google


[39] S.S. Pathade, B.S. Jagdale, J. Adv. Sci. Res.,

2020, 11, 87–94. [Google Scholar]

[40] V.A. Adole, P.B. Koli, R.A. Shinde, R.S. Shinde,

Mat. Sci. Res. India, 2020, 17, 41–53.


[41] V.A. Adole, R.H. Waghchaure, B.S. Jagdale,

T.B. Pawar, Chem. Bio. Interface, 2020, 10, 22–

30. [Google Scholar]

[42] S.S. Pathade, V.A. Adole, B.S. Jagdale, T.B.

Pawar, Mat. Sci. Res. India, 2020, 17, 27–40.


[43] R.A. Shinde, V.A. Adole, B.S. Jagdale, T.B.

Pawar, Mat. Sci. Res. India, 2020, 17, 54–72.


[44] A.R. Bukane, B.S. Jagdale, J. Adv. Chem. Sci.,

2021, 7, 717–720 [CrossRef], [Google Scholar]

[45] N.V. Sadgir, S.L. Dhonnar, B. Jagdale, B.

Waghmare, C. Sadgir, Mat. Sci. Res. India,

2020, 17, 281–293. [CrossRef], [Google


https://doi.org/10.1039/C6RA28613E

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=J.C.+Menezes%2C+RSC+adv.%2C+2017%2C+7%2C+9357-9372.Arylidene+indanone+scaffold%3A+medicinal+chemistry+and+structure%E2%80%93activity+relationship+view&btnG=

https://pubs.rsc.org/az/content/articlehtml/2017/ra/c6ra28613e

https://doi.org/10.3762/bjoc.13.48

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.+Turek%2C+D.+Szcz%C4%99sna%2C+M.+Koprowski%2C+P.+Ba%C5%82czewski%2C+Beilstein+J.+Org.+Chem.%2C+2017%2C+13%2C+451-494&btnG=

https://www.beilstein-journals.org/bjoc/articles/13/48

https://doi.org/10.1515/abm-2019-0052

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=%282E%29-2-Benzylidene-4%2C7-dimethyl-2%2C3-dihydro-1H-inden-1-one+%28MLT-401%29%2C+a+novel+arylidene+indanone+derivative%2C+scavenges+free+radicals+and+exhibits+antiproliferative+activity+of+Jurkat+cells&btnG=

https://sciendo.com/article/10.1515/abm-2019-0052

https://doi.org/10.1080/17415993.2020.1817456

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=DFT+computational+insights+into+structural%2C+electronic+and+spectroscopic+parameters+of+2-%282-Hydrazineyl%29+thiazole+derivatives%3A+a+concise+theoretical+and+experimental+approach&btnG=

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=DFT+computational+insights+into+structural%2C+electronic+and+spectroscopic+parameters+of+2-%282-Hydrazineyl%29+thiazole+derivatives%3A+a+concise+theoretical+and+experimental+approach&btnG=


https://doi.org/10.1080/08927022.2020.1800690

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=V.A.+Adole%2C+R.H.+Waghchaure%2C+S.S.+Pathade%2C+M.R.+Patil%2C+T.B.+Pawar%2C+B.S.+Jagdale%2C++Mol.+Simul.%2C+46%2814%29%2C+pp.1045-1054&btnG=

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=V.A.+Adole%2C+R.H.+Waghchaure%2C+S.S.+Pathade%2C+M.R.+Patil%2C+T.B.+Pawar%2C+B.S.+Jagdale%2C++Mol.+Simul.%2C+46%2814%29%2C+pp.1045-1054&btnG=


10.22036/PCR.2020.248964.1837

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=S.L.+Dhonnar%2C+V.A.+Adole%2C+N.V.+Sadgir%2C+B.S.+Jagdale%2C+Phys.+Chem.+Res.%2C+2021%2C+9%2C+193-209%2C+Structural%2C+Spectroscopic+%28UV-Vis+and+IR%29%2C+Electronic+and+Chemical+Reactivity+Studies+of+%283%2C+5-Diphenyl-4%2C+5-dihydro-1H-pyrazol-1-yl%29%28phenyl%29+methanone&btnG=

http://www.physchemres.org/article_122153.html

10.22036/PCR.2020.227546.1763

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=S.S.+Pathade%2C+B.S.+Jagdale%2C+Phys.+Chem.+Res.%2C+2020%2C+8%2C+671-687%2C+Experimental+and+Computational+Investigations+on+the+Molecular+Structure%2C+Vibrational+Spectra%2C+Electronic+Properties%2C+FMO+and+MEP+Analyses+of+4%2C+6-Bis+%284-Fluorophenyl%29-5%2C+6-dihydropyrimidin-2+%281H%29-one%3A+A+DFT+Insight.&btnG=

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=S.S.+Pathade%2C+B.S.+Jagdale%2C+Phys.+Chem.+Res.%2C+2020%2C+8%2C+671-687%2C+Experimental+and+Computational+Investigations+on+the+Molecular+Structure%2C+Vibrational+Spectra%2C+Electronic+Properties%2C+FMO+and+MEP+Analyses+of+4%2C+6-Bis+%284-Fluorophenyl%29-5%2C+6-dihydropyrimidin-2+%281H%29-one%3A+A+DFT+Insight.&btnG=

http://www.physchemres.org/article_110988.html

https://doi.org/10.1016/j.saa.2015.02.111

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.+Shkir%2C+S.+AlFaify%2C+H.+Abbas%2C+S.+Muhammad%2C+Spectrochim.+Acta+A+Mol.+Biomol.+Spectrosc.+SPECTROCHIM+ACTA+A%2C+2015%2C+147%2C+84-92&btnG=


https://doi.org/10.1016/j.molstruc.2014.11.070

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=A.+Srivastava%2C+R.+Mishra%2C+S.+Kumar%2C+K.+Dev%2C+P.+Tandon%2C++R.+Maurya%2C+J.+Mol.+Struct.%2C+2015%2C+1084%2C+55-73&btnG=


https://doi.org/10.1016/j.molstruc.2019.127394

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=Density+functional+studies+and+spectroscopic+analysis+%28FT-IR%2C+FT-Raman%2C+UV%E2%80%93visible%2C+and+NMR%29with+molecular+docking+approach+on+an+antifibrotic+drug+Pirfenidone&btnG=


10.22034/CHEMM.2020.107203

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=A.+Kumer%2C+M.J.+Islam%2C+S.+Paul%2C++Chemical+Methodologies%2C+2020%2C+4%285%29%2C+595-604&btnG=

http://www.chemmethod.com/article_107203.html

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=A.+Kumer%2C+N.+Sarker%2C+S.+Paul%2C+A.+Zannat%2C+Adv.+J.+Chem.+A%2C+2019%2C+2%283%29%2C+190-202&btnG=

http://www.ajchem-a.com/article_83694_9926.html

https://doi.org/10.32571/ijct.478179

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=A.+Kumer%2C+M.N.+Sarker%2C+P.A.U.L.+Sunanda%2C+Int.+J.+Chem.+Technol.%2C+2019%2C+3%281%29%2C+26-37&btnG=

https://dergipark.org.tr/en/pub/ijct/article/478179

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.J.+Islam%2C+A.+Kumer%2C+N.+Sarker%2C+S.+Paul%2C+A.+Zannat%2C+Adv.+J.+Chem.+A%2C+2019%2C+2%284%29%2C+316-326&btnG=

http://www.ajchem-a.com/article_87152.html


https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=J.R.+Hidalgo%2C+A.+Neske%2C+M.A.+Iramain%2C+P.E.+Alvarez%2C+P.L.+Bongiorno%2C+S.A.+Brand%C3%A1n%2C+J.+Mol.+Struct.%2C+2019%2C+1196%2C+508-517&btnG=



https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.+Raja%2C+R.R.+Muhamed%2C+S.+Muthu%2C+M.+Suresh%2C+J.+Mol.+Struct.%2C+2017%2C+1141%2C+284-298&btnG=



https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.A.+Iramain%2C+L.+Davies%2C+S.A.+Brand%C3%A1n%2C+J.+Mol.+Struct.%2C+2018%2C+1158%2C+245-254.&btnG=


https://doi.org/10.1016/j.molstruc.2020.129225

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=A.+Nath%2C+A.+Kumer%2C+M.W.+Khan%2C+J.+Mol.+Struct.%2C+2021%2C+1224%2C+129225.&btnG=

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=A.+Nath%2C+A.+Kumer%2C+M.W.+Khan%2C+J.+Mol.+Struct.%2C+2021%2C+1224%2C+129225.&btnG=


https://doi.org/10.1080/08927022.2020.1811866

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=M.M.+Hoque%2C+M.S.+Hussen%2C+A.+Kumer%2C+M.W.+Khan%2C+Mol.++Simul.%2C+2020%2C+46%2816%29%2C+1298-1307&btnG=


https://doi.org/10.33435/tcandtc.481878

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=A.+Kumer%2C+M.N.+Sarker%2C+S.+Paul%2C+Turkish+Comp.+Theo.+Chem.%2C+2019%2C+3%282%29%2C+59-68.The+thermo+physical%2C+HOMO%2C+LUMO%2C+Vibrational+spectroscopy+and+QSAR+study+of+morphonium+formate+and+acetate+Ionic+Liquid+Salts+using+computational+method&btnG=

https://dergipark.org.tr/en/pub/tcandtc/issue/43895/481878

http://dx.doi.org/10.13005/msri/170207

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=R.A.+Shinde%2C+V.A.+Adole%2C+B.S.+Jagdale%2C+T.B.+Pawar%2C+B.S.+Desale%2C+R.S.+Shinde%2C+Mat.+Sci.+Res.+India%2C+2020%2C+17%282%29%2C+146-161&btnG=

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=R.A.+Shinde%2C+V.A.+Adole%2C+B.S.+Jagdale%2C+T.B.+Pawar%2C+B.S.+Desale%2C+R.S.+Shinde%2C+Mat.+Sci.+Res.+India%2C+2020%2C+17%282%29%2C+146-161&btnG=

http://www.materialsciencejournal.org/vol17no2/efficient-synthesis-spectroscopic-and-quantum-chemical-study-of-23-dihydrobenzofuran-labelled-two-novel-arylidene-indanones-a-comparative-theoretical-exploration/

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=S.S.+Pathade%2C+B.S.+Jagdale%2C+J.+Adv.+Sci.+Res.%2C+2020%2C+11%2C+87-94&btnG=

http://dx.doi.org/10.13005/msri.17.special-issue1.06

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=V.A.+Adole%2C+P.B.+Koli%2C+R.A.+Shinde%2C+R.S.+Shinde%2C+Mat.+Sci.+Res.+India%2C+2020%2C+17%28specialissue2020%29%3A41-53.&btnG=

https://www.materialsciencejournal.org/specialissue2020/computational-insights-on-molecular-structure-electronic-properties-and-chemical-reactivity-of-e-3-4-chlorophenyl-1-2-hydroxyphenylprop-2-en-1-one/

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=V.A.+Adole%2C+R.H.+Waghchaure%2C+B.S.+Jagdale%2C+T.B.+Pawar%2C+Chem.+Bio.+Interface%2C+2020%2C+10%281%29%2C+22-30.Investigation+of+Structural+and+Spectroscopic+Parameters+of+Ethyl+4-%284-isopropylphenyl%29-6-methyl-2-oxo-1%2C+2%2C+3%2C+4-tetrahydropyrimidine-5-carboxylate%3A+a+DFT+Study.&btnG=


https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=S.S.+Pathade%2C+V.A.+Adole%2C+B.S.+Jagdale%2C+T.B.+Pawar%2C+Mat.+Sci.+Res.+India%2C+2020%2C+17%28special+issue2020%29%2C+27-40&btnG=

http://www.materialsciencejournal.org/specialissue2020/molecular-structure-electronic-chemical-and-spectroscopic-uv-visible-and-ir-studies-of-5-4-chlorophenyl-3-34-dimethoxyphenyl-1-phenyl-45-dihydro-1h-pyrazole-combined-dft-and-experimental-ex/


https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=R.A.+Shinde%2C+V.A.+Adole%2C+B.S.+Jagdale%2C+T.B.+Pawar%2C+Mat.+Sci.+Res.+India%2C+2020%2C+17%28specialissue2020%29%2C+54-72.+&btnG=

https://www.materialsciencejournal.org/specialissue2020/experimental-and-theoretical-studies-on-the-molecular-structure-ft-ir-nmr-homo-lumo-mesp-and-reactivity-descriptors-of-e-1-23-dihydrobenzob14dioxin-6-yl-3-345-trimethoxyphenylprop/

https://doi.org/10.30799/jacs.236.21070105

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=A.+R.+Bukane%2C+B.+S.+Jagdale%2C+J.+Adv.+Chem.+Sci.%2C+2021%2C+7%281%29%2C+717-720.&btnG=


https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=N.V.+Sadgir%2C+S.L.+Dhonnar%2C+B.+Jagdale%2C+B.+Waghmare%2C+C.+Sadgir%2C+Mat.+Sci.+Res.+India%2C+2020%2C+17%283%29%2C+281-293.+&btnG=

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=N.V.+Sadgir%2C+S.L.+Dhonnar%2C+B.+Jagdale%2C+B.+Waghmare%2C+C.+Sadgir%2C+Mat.+Sci.+Res.+India%2C+2020%2C+17%283%29%2C+281-293.+&btnG=

http://www.materialsciencejournal.org/vol17no3/synthesis-spectroscopic-characterization-quantum-chemical-study-and-antimicrobial-study-of-2e-3-2-6-dichlorophenyl-1-4-fluoro-prop-2-en-1-one/


187

[46] V.A. Adole, B.S. Jagdale, T.B. Pawar, B.S.

Desale, Mat. Sci. Res. India, 2020, 17, 13–36.


[47] V.A. Adole, T.B. Pawar, P.B. Koli, B.S. Jagdale,

J. Nanostructure Chem., 2019, 9, 61–76.


[48] V.A. Adole, R.A. More, B.S. Jagdale, T.B.

Pawar, S.S. Chobe, ChemistrySelect, 2020, 5,


[Publisher]

[49] R.H. Waghchaure, T.B. Pawar, World J.

Pharm. Res., 2020, 9, 1867–1881. [Google


[50] V.A. Adole, B.S. Jagdale, T.B. Pawar, A.A.

Sagane, S. Afr. J. Chem., 2020, 73, 35–43.


[51] B.S. Jagdale, S.S. Pathade, J. Appl. Chem.,

2019, 8, 12–19. [Google Scholar]

[52] S.S. Chobe, V.A. Adole, K.P. Deshmukh, T.B.

Pawar, B.S. Jagdale, Arch. Appl. Sci. Res., 6, 61–


[53] V.A. Adole, World J. Pharm. Res., 2020, 9,

1067–1091. [Google Scholar]

[54] N.V. Sadgir, S.L. Dhonnar, B.S. Jagdale, A.B.

Sawant, SN Appl. Sci., 2020, 2, 1–12.


[55] R. Basri, M. Khalid, Z. Shafiq, M.S. Tahir, M.U.

Khan, M.N. Tahir, M.M. Naseer, A.A.C. Braga,

ACS omega, 2020, 5, 30176–30188.


[56] N.V. Sadgir, S.L. Dhonnar, B.S. Jagdale, B.

Waghmare, C. Sadgir, Mat. Sci. Res. India,

2020, 17, 281–293. [CrossRef], [Google


[57] R. Bhuvaneswari, M.D. Bharathi, G.

Anbalagan, G. Chakkaravarthi, K.S. Murugesan,

J. Mol. Struct., 2018, 1173, 188–195.


[58] R.A. Shinde, V.A. Adole, J. Appl. Organomet.

Chem., 2021, 1, 48–58. [CrossRef], [Publisher]

[59] D. Pegu, J. Deb, S.K. Saha, M.K. Paul, U.

Sarkar, J. Mol. Struct., 2018, 1160, 167–176.


[60] V.A. Adole, B.S. Jagdale, T.B. Pawar, A.B.

Sawant, J. Chin. Chem. Soc., 2020, 67, 1763–


[61] S.L. Dhonnar, B.S. Jagdale, A.B. Sawant, T.B.

Pawar, S.S. Chobe, Der Pharma Chem, 2016, 8,

119–128. [Google Scholar]

[62] V.A. Adole, V.R. Bagul, S.A. Ahire, R.K. Pawar,

G.B. Yelmame, A.R. Bukane, J. Adv. Sci. Res.,

2021, 12, 276–286. [Google Scholar]

[63] M.J. Frisch, "Gaussian 03, revision C. 02;

Gaussian, Inc.: Wallingford, CT, 2004. [Google


[64] (a) A.D. Becke, J. Chem. Phys., 1993, 98,

5648–5652. [CrossRef], [Google Scholar]; (b)

A.D. Becke, J. Chem. Phys., 1993, 98, 1372–

1377. [CrossRef], [Google Scholar]

[65] (a) J.H. Jorgensen, J.D. Turnidge Manual of

Clinical Microbiology, Eleventh Edition:

American Society of Microbiology, 2015, p

1253. [CrossRef], [Google Scholar],

[Publisher]; (b) E.M. Johnson, M. Cavling-

Arendrup, Manual of Clinical Microbiology,

Eleventh Edition American Society of

Microbiology, 2015, p. 2255. [CrossRef],


[66] A. Kumer, M.N. Sarker, P.A.U.L. Sunanda,

Eurasian J. Environ. Res., 2019, 3, 1–10.


[67] M.N. Sarker, A. Kumer, M.J. Islam, S. Paul,

Asian J. Nanosci. Mater., 2019, 2, 439–447.


[68] M.K. Ahmed, A. Kumer, A.B. Imran, R. Soc.

Open Sci., 2021, 8, 202056. [CrossRef],


[69] V.A. Adole, J. Appl. Organomet. Chem., 2021,

1, 29–40. [CrossRef], [Publisher],

[70] T.B. Pawar, B.S. Jagdale, A.B. Sawant, V.A.

Adole, J. Chem. Biol. Phys. Sci., 2017, 7, 167–


[71] V.A. Adole, R.H. Waghchaure, T.B. Pawar, B.S.

Jagdale, K.H. Kapadnis, Asian J. Org. Med.

Chem., 2020, 242–248. [CrossRef], [Google


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https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=V.A.+Adole%2C+B.S.+Jagdale%2C+T.B.+Pawar%2C+B.S.+Desale%2C+Mat.+Sci.+Res.+India%2C+2020%2C+17%28special+issue2020%29%2C+13-36&btnG=

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https://link.springer.com/article/10.1007/s40097-019-0298-5

https://doi.org/10.1002/slct.201904609

https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=V.A.+Adole%2C+R.A.+More%2C+B.S.+Jagdale%2C+T.B.+Pawar%2C+S.S.+Chobe%2C+ChemistrySelect%2C+2020%2C+5%289%29%2C+2778-2786.&btnG=

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https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=R.H.+Waghchaure%2C+T.B.+Pawar%2C+World+J.+Pharm.+Res.%2C+2020%2C+9%286%29%2C+1867-1881%2C+SYNTHESIS%2C+CHARACTERIZATION%2C+MOLECULAR+STRUCTURE%2C+AND+HOMO-LUMO+STUDY+OF+2-PHENYLQUINOXALINE%3A+A+DFT+EXPLORATION&btnG=

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http://dx.doi.org/10.17159/0379-4350/2020/v73a6

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https://link.springer.com/article/10.1007/s42452-020-2923-9

https://doi.org/10.1021/acsomega.0c04653

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https://doi.org/10.1063/1.464913

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https://dergipark.org.tr/en/pub/ejere/issue/45416/478362

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https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=A+computational+study+of+thermophysical%2C+HOMO%2C+LUMO%2C+vibrational+spectrum+and+UV-visible+spectrum+of+cannabicyclol+%28CBL%29%2C+and+cannabigerol+%28CBG%29+using+DFT&btnG=

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:%20https:/doi.org/10.14233/ajomc.2020.AJOMC-P285

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