SYNTHESIS AND EVALUATION OF SUBSTITUTED BENZOFURAN DERIVATIVES OF BIOLOGICAL INTEREST.

M.PHARM

DISSERTATION PROTOCOL

Submitted to the

RAJIV GANDHI UNIVERSITY OF HEALTH SCIENCES, BANGALORE KARNATAKA

By

MR. SYED SARFRAZ ALI

B.Pharm

Under the guidance of

DR. RAGA BASAWARAJ

M.Pharm. Ph.D

PROFESSOR

DEPARTMENT OF BULK DRUGS

DEPARTMENT OF BULK DRUGS

K.R.E. SOCIETY’S KARNATAKA COLLEGE OF PHARMACY, MANHALLI ROAD, BIDAR – 585 403.

2

RAJIV GANDHI UNIVERSITY OF HEALTH SCIENCES,BANGALORE, KARNATAKA

Annexure- IIProforma for Registration of Subjects for Dissertation

1 Name of The Candidate And Address ( In Block Letters )

SYED SARFRAZ ALIH-No-2-5-55 (New) Pansal Taleem Near Fathedarwaza , Bidar – 584 501 (KARNATAKA)

2 Name of The Institution KARNATAKA COLLEGE OF PHARMACY, BIDAR – 584 503

3 Course of study and subject M. PHARM(BULK DRUGS)

4 Date of Admission to Course 06-07-2010

5 Title Of The Topic :SYNTHESIS AND EVALVATION OF SUBSTITUTED

BENZOFURAN DERIVATIVES OF BIOLOGICAL INTEREST.

6 Brief resume of the intended work:6.1 Need For The Study Enclosure-I6.2 Review Literature Enclosure-II6.3 Objective Of The Study Enclosure-III

7 Materials And Methods :7.1 Sources Of Data Enclosure-IV7.2 Methods Of Collection Of data Enclosure-V7.3 Does the study require any investigation or intervention to be conducted on patients or humans and animals? If so please describe briefly: … Yes …. 7.4 Has ethical clearance been obtained from yours institution? If so please describe briefly: …Applied …

8 List of References Enclosure-VI

3

9 Signature of the candidate SYED SARFRAZ ALI

10 Remarks of the guide Satisfactory

11 Name and Designation (in block letter)11.1 Guide

11.2 Signature

11.3 Co-guide (if any)

11.4 Signature

11.5 Head of Department

11.6 Signature

DR. RAGA BASAWARAJ M.Pharm. Ph.D

PROFESSOR DEPARTMENT OF BULK DRUGS

--

DR. KASHINATH NAUBADE M.Pharm. Ph.D

PROFESSOR AND H.O.D.DEPARTMENT OF BULK DRUGS

KARNATAKA COLLEGE OF PHARMACY, BIDAR.

12 12.1 Remarks of the chairmen and Principal

12.2 Signature with seal

Prof. KRANTIKUMAR SIRSE M.PHARMA (Ph.D)

PRINCIPALKARNATAKA COLLEGE OF

PHARMACY, BIDAR.

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ENCLOSURE- I

6. BRIEF RESUME OF THE INTENDED WORK

6.1 Need for the study

The present research programmed is focused on the design and development of new

antimicrobial, antitubercular, antihypertensive and antidiabetic agents and it is justified because

more organisms being resistance to the present available drugs in the market.

The advances made in the synthesis of organic compounds, knowledge of enzymes &

their structures & of other biochemical basis of the physiological processes helped in

understanding the disease & consequently their cure by drugs.

The integrity of the drug molecule optimization of pharmaceutical effects, uniform and

consistent availability of drug from the dosage.

Word wise pharmaceutical research are working day and night to synthesize new drug

molecule usually better pharmaceutical and better dynamic properties with less side effects and it

is necessary to replace order drug by newer drug molecule.

Therefore in view of the above facts, we planned to synthesize some new substituted

benzofuran derivatives of biological interest.

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ENCLOSURE- II

6.2 Review of Literature:-

Literature survey suggests that extensive synthetic work on Synthesis and evaluation of

substituted benzofuran derivatives of biological interest. Our main goal is to study the synthesis

of some new benzofuran derivatives and evaluated for their better activities.

The chemistry of benzofuran owes its importance mainly to the frequent occurrence of

this nucleus in natural products. Such natural products which have structures ranging from

simple benzofuran derivatives to highly complicated molecules like retinoid and morphine are

often endowed with use ful therapeutic properties. Benzofuran nucleus is frequently associated

with oxygen heterocyclic like α – pyrone , γ – pyrone, chromone etc. However the association of

benzofuran nucleus in natural product with nitrogen heterocycles is less common. Even though

voluminous work has been done on benzofuran monographs devoted to the study of both natural

and synthetic benzofuran have appeared in literature1-5.

During last few years interest in this area was focused on the synthesis and evaluation of

biological activities of various benzofuran coupled with heterocyclic moieties such as pyrazole,

thiazole, oxadiazole, pyrimidines etc.

In view of the significance of biological properties of benzofuran and other nitrogen

heterocyclic a systematic evaluation of fused heterocyclic and heterocyclic of benzofuran was

undertaken and result have been published in a series of paper 6-10.

Based on these observations and in continuation of our research work on synthesis of

biologically active heterocyclic compounds, we now planned to synthesise some new benzofuran

derivatives of biological interest.

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1. Raga Basawaraj, and coworker12. Reported the synthesis and antitubercular activities of

azetidinone and thiazolidinone derivatives from 5-chloro-3-methrylbenzofurans.

3-{[(1E)-1-(5’-Chloro-3’-methyl-1’-benzofuran-2’-yl)ethylidine]amino}-2-substituted phenyl-1,3-thiazolidin-4-ones

2. Vijaykumar Tirlapur, and coworker13. Reported the synthesis and biological activities

of some new substituted benzofuranopyridines.

6-(5-bromo-1-benzofuran-2-yl)-2-amino-4-(substituted phenyl)nicotinonitriles.

3. Vijay Kumar Tirlapur and coworker14. Reported the synthesis and biological activities

of some new benzofuranopyrazoles.

3-(5-bromo-1-benzofuran-2-yl)-1H-pyrazole-4-carbaldehyde 3

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4. J.K. Makrandi , and coworker 15. Reported the synthesis of isatin-3-[benzofuran-2-yl]-2’-

thiazolyl]-hydrazones.

Isatin-3-[(benzofuran-2-yl)-2’-thiazolyl]hydrazones

5. J.K. Makrandi , and coworker16. Reported the microwave assisted synthesis and

antimicrobial activity of 3-[(benzofuran-2-yl)acylthio]-5H-as-triazino[5,6-b] indoles.

3-[(benzofuran-2-yl)acylthio]-5H-as-triazino [5,6-b]indoles

6. Ling-Yi Kong, and coworker17. Reported the synthesis of benzofuran derivatives via rearrangement and their inhibitory activity on acetylcholinesterase.

3-bromo-6-methyl-4-morpholinocoumarin

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7. D. R. Harish Kumar, and coworker18. Reported the synthesis of benzofuran derivatives and their evaluation of antimicrobial activity.

4-[1-benzofuran-2-yl]-1-[1,3-benzothiazol-2-yl]-3-azetidin-2-one

8. Magdy I. El-Zahar, and coworker19. Reported the synthesis and cytotoxic evaluation

of some novel 6-(benzofuran-2-yl)-4-(4-fluorophenyl) pyridines.

2-[(4-substituted-5-thioxo-1,2,4-triazolin-3-yl)methoxy]-6-(benzofuran-2-yl)-4-(4-fluorophenyl)pyridine-3-carbonitriles

9

9. Raga Basawaraj, and coworker20. Reported the synthesis of various azetidinone and

thiazolidinone derivatives from 5-chloro-3-methyl-2-(2’-aminothiazole-4’-yl) benzofuran

and their biological activities.

5-chloro-3-methyl-2-[2’ (2”aryl-4”-oxo-thiazolidine-3”yl)thiazole-4’-yl]benzofurans

10. Mohamoud Reza Heidari, and coworker21. Reported study of the anti-inflamatory and

analgesic effects of novel rigid benzofuran-3, 4-dihydroxy chalcone by formalin,

hot-plate and carrageenan tests in mice.

(Z)-2-(3,4-dihydroxybenzylidene)-5-methoxybenzofuran-3(2H)-one

11. Raga Basawaraj, and coworker22. Reported the synthesis and pharmacological

activities of 5-chloro-3-nethylbenzofuran incorported pyrimidines and isoxazolines.

2-aryl-4-(5’-chloro-3’methylbenzofuran-2’-yl)isoxazolines

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12. P.M. Gurubasavaraja Swamy, and coworker23. Reported the synthesis and antimicrobial

activity of 3-(3’-hydroxy benzofuranyl)-5- aryl-pyrazolines.

3-(3’-hydroxy benzofuran-2’-yl)-5-aryl-pyrazolines

13. Raga Basawaraj, and coworker24. Reported the synthesis and biological activity of

some pyridyl substituted benzofurans.

2-amino-4-aryl-6-(benzofuran-2’-yl)-3-cyanopyridines

14. Raga Basawaraj, and coworker25. Reported the synthesis and biological evaluation of

benzofuro [3,2-d] pyrimidines.

4-pyrrolidino/piperidino/morpholino-2-(3,4,5-trimethoxyphenyl)benzofuro[3,2-d]pyrimidines

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15. Sushila S.Sangapure, and coworker26. Reported the synthesis of new benzofuran

analogues from 5-bromosalicylaldehyde and their biological activities.

16. Raga Basawaraj, and coworker27. Reported the synthesis of some 3-aryl-2-(5’-chloro-3’-

methylbenzofuran-2’-yl)-1, 4-quinoxalyl methanes of biological interest.

3-aryl-2-(5’-chloro-3’-methylbenzofuran-2’-yl)-1,4-quinoxalyl methanes

17. P.M. Gurubasavaraja Swamy, and coworker28. Reported the synthesis and antimicrobial

activity of some novel chalcones containing 3-hydroxy benzofuran.

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18. Raga Basawaraj, and coworker29. Reported the synthesis of some benzodiazepines and benzothiazepines bearng benzofuran moiety as possible CNS depressants.

2-aryl-3-(5’-chloro-3’-methylbenzofuran-2’-yl)-1,5-dihydrobenzothiazepine

19. Raga Basawaraj, and coworker30. Reported the reaction products of 2-substituted-4-

chlorobenzofuro [3,2-d] pyrimidines and their antimicrobial activities.

2-(3,4,5-trimethoxyphenyl/ -naphthyl)-3,4-dihydro-4-thiobenzofuro [3,2-d]pyrimidines

20. Basawaraj R., and coworker31. Reported the synthesis and biological evaluation of some

new benzofuran derivatives.

5-chloro-3-nethylbenzofuran-2-carbothiosemicarbazide

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21. Samia M. Rida, and coworker32. Reported the synthesis and in vitro evaluation of some

novel benzofuran derivatives as potential anti-HIV-1, anticancer, and antimicrobial agent.

6-(1-benzofuran-2yl-ethylideneamino)-5-methyl-3-substituted-2-thiozo-2,3-dihydro-6H-thiazolo[4,5-d]pyrimidin-7-ones

22. M.Bhagavan Raju and coworker33. Reported the synthesis and antimicrobial activity of

2-[(5-substituted aryl-1’-N-substituted aryl aminomethyl) pyrazol-3-yl] benzofurans.

2-[(5-substituted aryl-1’-N-substituted aryl amino methyl) pyrazol-3-yl] benzofurans

23. M. Bhagavan Raju and coworker34. Reported the synthesis and antimicrobial activity of

1,2,4- triazolyl benzofurans.

2-(4-acetylamino substituted amino-5-mercapto-1,2,4-triazol-3-yl) 3-hydroxy benzofurans

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24. K.M. Basavaraja and coworker35. Reported the synthesis and nucleophilic displacement

reactions of biologically active 2,4-dichlorobenzofuro [3,2-d] pyrimidines.

3,4-dihydro-2-chloro-4-oxobenzofuro [3,2-d]pyrimidines

25. Raga Basawaraj and coworker36. Reported the synthesis and biological screening of some

new 2-N-arylaminoacetyl-5-chloro-3-methylbenzofurans.

2-N-arylaminoacetyl-5-chloro-3-methylbenzofurans

26. K.M. Basavaraja and coworker37. Reported the synthesis and reactions of biologically

active 1,2,3,4-tetrahydro-4-oxo-2-thiobenzofuro [3,2-d] pyrimidine derivatives.

[1,5-a]-3-N-alkyl/aryl-4-oxopyrimidino [5,4-b] benzofurans

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27. A.R. Mishra, and coworker38. Reported the synthesis and fungicidal activity of benzofuran incorporated substituted pyrimidines.

4-(2-benzofuran)-6-(4’-arylphenyl)-2-hydroxypyrimidines

28. Vijay N. Pathak, and coworker39. Reported the facile synthesis of fluorine containing

2-aroylbenzo[b]furans via microwave assisted solventless phase transfer catalysis.

2-aroylbenzo [b] furans

29. K.M. Basavaraja and coworker40. Reported the synthesis and biological activity of

4-aryl benzofuro [3,2-d] pyrimidine-3-N-oxides and 3-(3’-aryl-1’,2’,4’-triazol-4’-yl)

benzofurans.

2-aroyl-3-(3’-alkyl/aryl-1’,2’,4’-triazol-4’-yl)-benzofuras

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30. Raga Basawaraj, and coworker41. Reported the synthesis and pharmacological activities of some 2-arylamino/arylidene hydrazino-4-(5’-chloro-3’-methylbenzofuran-2’-yl)

thiazoles.

.

2-arylidene hydrazine-4-(5’-chloro-3’-methylbenzofuran-2’-yl) thiazoles

31. De Quan YU and coworker42. Reported a new benzofuran derivative from the bark of

mulberry tree.

32. Kadriye benkli, and coworker43. Reported the synthesis and antifungal activities of some

aryl (3-methyl-benzofuran-2-yl) ketoximes.

aryl (3-methyl-benzofuran-2-yl) ketoximes acetates

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33. Raga Basawaraj and coworker44. Reported the synthesis of some 1H-pyrazolines bearing

benzofuran as biologically active agents.

5-aryl-3-(5-chloro-3-methyl benzofuran-2-yl)-1-acetyl pyrazolines

34. (Smt.) S.S. Sangapure and coworker45. Reported the synthesis of some benzofuro [3,2-d]

pyrimidine derivatives as antibacterial and antifungal agents.

2-(4-methoxyphenyl)-3,4-dihydro-4-mercaptobenzofur [3,2-d] pyrimidines

35. Y.S. Agasimundin, and coworker46. Reported the synthesis and some reactions of

benzofuran analogues of 2-aminochalcones.

2-phenyl-1,4-dihydorobenzofuro[2,3-b]pyridine-4-one

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ENCLOSURE- III

6.3 Objective of the Study:-

During the present course of investigation we planned to synthesize some new

benzofuran derivatives.

The newly synthesized molecules will be established on the basis of physical data,

analytical data and spectral studies such as IR, 1H NMR, 13C NMR and mass spectra. All

synthesized compounds were screened for their biological and pharmacological activities on the

basis of literature survey

The results of biological and pharmacological activities of the synthesized compounds

were compared with standard drug and also discussed about their structural activity relationship.

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ENCLOSURE- IV

7. MATERIALS AND METHODS

7.1 Source of data:-

In the present research programme, we planned to synthesize some new benzofuran derivatives. This synthetic work mainly a laboratory based work. All the basic facilities required for the synthesis of new benzofuran derivatives are available in our college laboratory. The facilities like glassware, heating mantle, distillation assembly, melting point apparatus, vacuum pump, chromatography apparatus & IR spectrophotometer etc is also available in our college laboratory.

The literature survey pertaining to present investigation will carried out by referring

chemical abstracts, internet, national and international journals. The information about the

synthesis & biological evaluation parameters will be collected by referring to Indian journal of

heterocyclic chemistry, journal of Indian chemical society, journal of heterocyclic chemistry,

Indian journal of chemistry, journal of medicinal chemistry, Chinese chemical letters, European

journal of medicinal chemistry, chemical abstracts etc .For this purpose library & internet

facilities are available in our college. Also Rajiv Gandhi University of Health Science Bangalore,

Indian institution of science Bangalore Indian institution of chemical technology, Hyderabad will

be made use.

The day to day development in the area will be updated by literature survey through

e-publishing, internet and current periodicals in our library and else where.

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ENCLOSURE- V

7.2 Method of collection of data:-

The chemical structure of synthesized compounds will be elucidated on the basis of

physical, chemical and analytical data. Melting point of all compounds will be determined in

open capillary tube and an uncorrected; they are expressed in degree centigrade.

The compounds synthesized drug present research programme will be characterized by

IR, 1HNMR and Mass Spectral data. This will be collected by sending the sample to other

advanced research center.

The main aim of the present investigation is to explore newer molecule with potent

biological and pharmacological activities

All newly synthesized compounds were evaluated for antimicrobial activity by

cup-plate diffusion method11.

Some selected compounds were screened for pharmacological activities such as anti-

inflammatory, analgesic and diuretic activity11.

7.3 Does the study require any investigation to be conducted on patients or other

human or animals? If so, please describe briefly.

Yes, at the later stage, after successful synthesis of molecules. The compound will be

screened for pharmacological actions on albino mice and rats.

7.4 Has ethical clearance been obtained from your institution in case?

Yes ethical clearance committee had been obtained by our Institution.

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ENCLOSURE-VI

8. LIST OF REFERENCE:

1. Dolique R, Traite de chimie organique 18, Masson, Paaries (1935).

2. Meyer V B, Heterocyclic compounds” (Ed. By Elder Field), 2,65, Wiely New York, (1951).

3. Stevens T S, Chemistry of Carbon Compounds (Ed. By E.M. Rodd) IV , Elsssevier Amsterdam (1957).

4. Dean F M, Naturally occurring oxygen ring compounds, Butter Worths and co-London (1963).

5. Mustafa A, Furopyrans and Furopyones (Ed. By Weissberger). Interscience Publisher. London, New York (1967).

6. Small L F, Eddy N B, Moesetting E and Himmeisbach L K, Studied on Drug Addiction, Public Health Dept. Suppl., 113 (1938).

7. Sangapure S S and Agasimundin Y S, Indian J.Chem. 14B, 688 (1976).

8. Sangapure S S, and Agasimundin Y S, Indian J.Chem. 15B, 485 (1977).

9. Mahajan S B, and Agasimundin Y S, Indian J.Chem. Sco., LIV 965 (1977).

10. Sangapure S S, and Agasimundin Y S, Indian J.Chem. 16B, 627 (1978).

11. Indian Pharmacopoeia, Vol. II (Controller of Publication Delhi) 1996

12. Raga Basawaraj, Amith.L, Vijaykumar.T, Havangirao.M and Upendra.C.H International Journal of ChemTech Research. Vol.2, No.3, pp 1764-1770, (2010)

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13. Vijaykumar Tirlapur, Raga Basawaraj and Y.Rajendra Prasad Indian Journal of Heterocyclic Chem. Vol 20 , pp. 49-52 (2010)

14. Vijay Kumar Tirlapur, Y.Rajendra Prasad and Raga Basawaraj Indian Journal of Heterocyclic Chem. Vol. 20, pp 57-60, (2010)

15. J.K. Makrandi and Rekha Rani Indian Journal of Heterocyclic Chem.

Vol. 19, pp 393-396, (2010)

16. J.K. Makrandi and Rekha Rani Indian Journal of Heterocyclic Chem.

Vol. 19, pp 305-306, (2010)

17. Ling-Yi Kong Xiang Zhou , Miao Li , Xiao-Bing Wang and Tao Wang Molecules Journal (2010),

15, pp 8593-8601

18. D. R. Harish Kumar and M.D. Karvekar E-Journal of Chemistry Vol. 7(2), pp 636-640, (2010)

19. Magdy I. El-Zahar, Somaia S. Abd EL-Karim and Mogedda E. Haiba World Journal of Chemistry 4 (2) ISSN 1817-3128, pp 182-194, (2009)

20. Raga Basawaraj, Srikanth Patil, Ashok Patil, T.Vijaykumar, G.Parmeshwarappa An Indian Journal OCAIJ, 5(1), (2009), pp 68-72

21. Mohamoud Reza Heidari, Alireza Foroumadi, Hojat Noroozi, Ali Samzadeh-Kermani And Behzad Sarvar Azimzadeh Pak.Journal Pharma Science, Vol. 22, No. 4 pp 395-401 (2009)

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22. Raga Basawaraj, Ashok Patil and Y. Rajendra Prasad Indian Journal of Heterocyclic Chem. Vol. 18 pp 235-238, (2009)

23. P.M. Gurubasavaraja Swamy and Y.S. Agasimundin Indian Journal of Heterocyclic Chem. Vol. 18 pp 275-278, (2009)

24. Raga Basawaraj, S.N. Goled, G. Parmeshwarappa and S.S. Sangapure Indian Journal of Heterocyclic Chem. Vol. 18 pp 325-328, (2009)

25. Raga Basawaraj, Goled Shashikanth, M.H. Hugar and S.S. Sangapure Indian Journal of Heterocyclic Chem. Vol. 18 pp 329-332, (2009)

26. Sushila S.Sangapure, Gangajji Parameshwarappa, Raga Basawaraj An Indian Journal OCAIJ, 4(5), pp 375-379 (2008)

27. Raga Basawaraj and S.S. Sangapure Int. J. Chem. Sci.¨6(1), pp 351-357 (2008)

28. P.M. Gurubasavaraja Swamy and Y.S. Agasimundin Acta Pharmaceutical Sciencia, 50 pp 197-202 (2008)

29. Raga Basawaraj, Kashinath Naubade and S.S. Sangapure Indian Journal of Heterocyclic Chem. Vol. 17 pp 217-220, (2008)

30. Raga Basawaraj, S.N. Goled, G.Kalaskar and S.S. Sangapure Indian Journal of Heterocyclic Chem. Vol. 18 pp 01-04, (2008)

31. Sangapure S.S. Basawaraj R., and Parameshwarappa G. Indian Drugs 44(1), pp 08-12, (2007)

32. Samia M. Rida, Soad A.M. EI-Hawash, Hesham T.Y. Fahmy, Aly A. Hazza, and Mostafa M.M. EI-Meligy Archibes of Pharmacal Research Vol. 29, No 1, pp 16-25, (2006)

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33. M.Bhagavan Raju Rajesh Kumar, VVS Rajendra Prasad, Y.C. Mayur, and S.M. Shanta Kumar Indian Journal of Heterocyclic Chem. Vol. 15 pp 245-248, (2006)

34. M. Bhagavan Raju, Rajesh Kumar, VVS Rajendra Prasad, Y.C. Mayur, and S.M. Shanta Kumar Indian Journal of Heterocyclic Chem. Vol. 15 pp 287-288, (2006)

35. K.M. Basavaraja V.M. Patil and Y.S. Agasimundin Indian Journal of Heterocyclic Chem. Vol. 15 pp 313-318, (2006)

36. S.S. Sangapure Raga Basawaraj, and G. Parameshwarappa Indian Journal of Heterocyclic Chem. Vol. 16 pp 75-76, (2006)

37. K.M. Basavaraja V.M. Patil and Y.S. Agasimundin Indian Journal of Heterocyclic Chem. Vol. 16 pp 159-162, (2006)

38. A.R. Mishra, D.V. Singh, and R.M. Mishra Indian Journal of Heterocyclic Chem. Vol. 14 pp 319-322, (2005)

39. Vijay N. Pathak, Ragini Gupta and Neetu Gupta Indian Journal of Heterocyclic Chem. Vol. 14 pp 355-356, (2005)

40. K.M. Basavaraja V.P. Vaidya and Y.S. Agasimundin Indian Journal of Heterocyclic Chem. Vol. 15 pp 01-06, (2005)

41. S.S. Sangapure, Raga Basawaraj, and Suresh Madhur Indian Journal of Heterocyclic Chem. Vol. 15 pp 153-156, (2005)

42. De Quan YU, Sheng Jun DAI, Zhi Bo MA, Shuai LI, and Ruo Yun CHEN, Chinese Chemical Letters Vol. 15, No. 8, pp 951-953, (2004)

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43. Kadriye benkli, nalan gundogdu-karaburun ahmet cagri karabururn, umit ucucu, seref demirayak, and nuri kiraz archibes of pharmacal research vol. 26, No 3, pp 202-206, (2003)

44. S.S. Sangapure, Raga Basawaraj, and Bodke Yadav Indian Journal of Heterocyclic Chem. Vol. 11 pp 31-34, (2001)

45. (Smt.) S.S. Sangapure, D.H. Veeresh and Bodke Yadav Indian Journal of Heterocyclic Chem. Vol. 10 pp 21-26, (2000)

46. Y.S. Agasimundin, Ujjinimatada Ravi K, G S Harwalkar, and N V Kalyani Indian Journal of Chemistry. Vol. 39B, pp 587-591, (2000)

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