Indian Journal of Chemistry Sect. B: Organic Chemistry including Medicinal Chemistry

VOL. 38B NUMBER 9 SEPTEMBER 1999

1011

1015

CONTENTS

Rapid Communications

Chemoenzymatic synthesis of enantiopure (+)­presqualene diphosphate analogues

Pseudomonas putida 39D

Escherichia coli JM109 (pOTG601)

Martin G Banwel\*, Grant S Forman &

David C R Hockless

•

Interesting reaction of 2,2'-binaphthol with 1,2-dibromoethane: Synthesis of a novel spiro­dienone

OH

OH

A R Ramesha, Kodumuru Vishnumurthy, Tayur N Guru Row & Srinivasan Chandrasekaran*

cis-I, 2-Dihydrocatechol 2, u product or mi crobial ox i­dation of toluene, has bcen converted into the enunti o­pure analogues 24-27 of presqu alene diphosphate (PSDP, 1).

2,2'-Binaphthol 1 reacts with 1,2-dibromoethane in th..: presence of potassium carbonate to give ri se to a nove l spirodienone system 3 and its structure has been COIl ­

firmed by X-ray analysis.

~Br K:PJ3 Br .

(i)

DMF,~ 20 hr

.. 3

INDIAN.J CHEM, 38B (9) 1999

CONTENTS

Advances in Contemporary Research

1018 Natural taxols Taxo ls, thc· N-acyICN-alkyl)-phenylisosCrllle csters of baecat in III-type taxoids , have becn reported from di ITcr­ent yew plants (TaxlIs species) . The literature cOllcern ing the chemi stry and bioactivity of thesc comlxlllmb has bcen brie lly rcviewed.

Biswanath Das*, A Kashinatham &

G Anjani

Papers

HO OBz OA c

1025 Bioconversions of citral and C±)-cil.ronellol by Microbial reductions of citral and (±)c itroncllo l hy Sac-

1030

Saccharomyces cerevisae-2415 charol1l),ces cerevisae is reported .

T Chatterjee, B K De & D K Bhattacharyya*

Solid phase peptide synthesis using a new PS­TTEGDA resin: Synthesis of pardaxin (1-26)

~CH=O ~CH20H H · s. cerevisae ~ """'H

H 0 H 30 - 32 C(3 days)

3

~CH=O ZCHPH

H S. cerevisae H H ~ H

30 - 32 °C(3 days)

2 4

Development of new tlexible polymer supports i"cl r the synthesis of bioactive peptidcs is reported .

8oc-Gly-Phe-Phe-Ala-Leu-lle-Pro-Lys(CICbz)-lle··lle-Ser(8zl)-Ser(8zl)-Pro-Leu- Phe­

LYS(CICbZ)-Thr(8ZI)-LeU-LeU-Ser(8ZI)-Ala-Val-GIY-Ser.(BZI)-Ala-Le\:!)'--0-16

lTFA: Thioanisol : m-Cresol . (10:1 :1) 400 C

M Renil*, V N Rajasekharan Pillai*,

S Thennarasu & R Nagaraj

Pardaxin 1-26

(ii) INDIAN J CHEM, 38H(9) 1999

1036 Condensation of 2,3-pyridinediamines with Condensation of 2,3-pyridined iamines 1 with acc-

1041

1046

acetonylacetone tonylacetone gives 2 whose structure is suppo rted by its reaction with HONO to yield 4 whi ch is also prepared alternatively in an authentic way. The reacti vity of 2 with electrophilic reagents has been studied .

:n't< N NH:1

Na~.X~'q aq.HCVOoC ~N~OH

1 2 4 (X = H or Br)

P K Dubey* & R Vinod Kumar

Condensation of a-phenylenediamine with phenylpropiolic acid

Condensation of o-phenylenediamine dihydrohalides (I . 2HX, X=CI or Br) with 2 in refluxing ethylene glycol yield 2-p-haloarylvinylbenzimidazo les (i.e. 3, X=CI; 4. X=Br). The mechanism of formation of 3 and 4 has been discussed. Compounds 3 and 4 when treated with pot. tert . butoxide in DMSO at 1000 gi ve 2- p-phenyl­acetylenylbenzimidazole 5.

H H

(XNH:1 _e_Ih....:;y_le_n_e .. (XI N: L/Al I . 2HX + HOOC-C=C-Al .. Y 1 "- glycol l ot. ~ N X ...... , NH:1

KOBu l

P K Dubey* , Ramesh Kumar, J S Grossert* &

D L Hooper*

Anodically generated manganese (III) sul­phate for the oxidation of aldo- and keto­hexoses: A kinetic and mechanistic study

1

N Anitha, K S Rangappa* &

K M Lokanatha Rai

+

2

H

(XN I rC=C-Al

~ N

5

3, X=CI ; 4, X=Br

Oxidation of hexoses 1 by manganese (III ) in the pres­ence of sulphate ions in acidic medi um to the corre­sponding aldaric acids 2 and Mn(II ): Kineti cs and mechanism.

305 K + 2

(iii) INDIAN J CHEM, 3813 (9) 1999

CONTENTS

1052 Synthesis of purines and azapurines

1066

C J Shishoo*, K S Jai n, S R Jain. V S Shirsath

& T Ravikuma r

Syn thesis and antibacteria l activities of 1, 3, 4-thiadiazole, 1, .3. 4-oxadiazole and 1, 2, 4-triazole d eriva tivl"s of 5-methylisoxazol e

3a-d

Xin-Ping Hui, Lin-Mei Zhang, Zi-Yi Zhang*, Qin Wang & Fang Wang

The synthesis of a novel serics uf CiX) ull , ubst itutcu l1a-h, C (X) substituted 12a-e, 8-mercapt o- 13a-c. 1,3 -diaryl-2-thiox ant hines, as well as , 8-aza-l . J-diaryl-2-thi oxanthines 14a-g. through precursors, 5 , 6-di alll ino-l. 3-diaryl -2-thiouracil s 10 via the rcducti on of the int er­mediate 5-nitroso-6-ami no- I , 3-di aryl-2-thiuuraeils 9.

j10

1C dono r

14

A series of thi oscmicarbazides 2a-h . I . 3. 4- thi ad iawks 3a-d, I , 2, 4- tri azoles 4 , S and I , 3 , 4 -oxidazo les 7, 9 have been synthesi zed from 5-mcthyli suxazu l-3-aeetil· ac id hydrazide 1. Some o f them have heen tested for antibacterial activi ties .

(iv)

7 R,=NHPh

9 R,=SC H3

(ONHNHCSNHCOAr

)l--v, N 2a-h Me "'-0;

N-N

JZ~ In'( 'N SH

A _;N I Me 0.... R2

IN DIAN J CHEM, 38U(9) 1999

1070

1075

Synthesis and antimicrobial activity of some new 2-aminomethyl-5-(4-phenyl-5-mercapto-1, 2, 4-triazol-3-yl)methoxyindoles

2-Aminomethylindole di esters 3a-b react cheJlloselec­tively with hydrazine hydrate to yield Jllonocarhuhy­drazides 5a-b whi ch are further roverted to 2-aJllino­methyl-5-(4-phenyl -5 -m.:rcapto- l , 2, 4-tri azol-3-yllmcth­oxyi ndole derivatives. All these new compounds have been screened for an tibacterial and ant ifunga l activiti es .

H N~N

COOC, Hs COOC2Hs s=( II COOC2H, HSC:!OOC,---,0XX)- N2H,.H,o H2NHNOC,---,0XX)- N~0x:Q-

I ~ CH2-R · I ~ CH:1 -R - / I ~ CH, - R

B "" N Bhanol B "" N (415 B "" N r I r I r I

n-Bu n-Bu n- Bu

3a-b 5a-b 8a- b

G S Gadaginamath* & S A Patil

Synthesis of novel J , 2-(un) substituted-3-amino-5-aryl-6-arylaminopyrazoloL3,4-d]pyri­midin-4(5H)-ones and their biological activi­ties

C J Shishoo*, T Ravikurnar, K S Jain,

! S Rathod, T P Gandhi & 1\01 C Satia

A novel series of I, 2-(un)substituted-3-;1I11ino-5-aryl-6-arylami nopyrazolo[3,4-d]pyrimidin-4(5Hl-ones 5-7 have been synthesised through the cyciocundensation <11" 1 he corresponding, hitherto unreported 3-aryl-2-ar 'lalllino-5-cyano-6-met.hylthio/su lfonylpyrimidin -4-oncs 3 ,)r 4 with hydrazine hydrate or substituted hydrazincs. Compounds 6a and 7a exhibit analgesic activity superior to that of the standards, aspirin and pentazocine. Thesc compounds also ex hibit significant an ti-intl ammatory ac tivity compa­rable to that of diclofenac sodium. The free rad ical 5C; 11' ­

enging activity, as well as, the ul cerogenic potential or some of the act ive compounds in the ,c ri e~ ha, also heen determined .

---------------------------------------------------

(\') INDIAN J CHEM, 38B (9) J999

1086

1090

1093

CONTENTS

Synthesis of O,O-diaryl 0-II-propyl phos­phorothionates and their fungitoxicity against Rhizoctollia soLani and SclerotiulII ro(fsii

O,O-Di aryl 0-II-propyl phosphorothi onatcs ha vc hec n prepared by reacting thiophosphoryl tri chl ori de wi th 11-

propanol foll owed by co ndensat ion with substi tuted phe­nols and their fun gitox icity stud ied again st N. SO /Oil ; and S. rolfsii. O,O-Di (3-methylphenyl) 0 -II-propyl phllS­phorothionate is most effective against R. solon ; and O,O-di (2, 3-dimethylphenyl ) 0-II -pro pyl phos phoro­thionate a!!ai nst S. rolfsii.

s CsHsN • CH3C1-LCH2- 0 - r- CI2 PSCI3 + CH3C~C~OH --- ' '<

Dipankar Patra & R L Gupta*

Isolation and structure elucidation of some pseudoguaianolides from Parlhelliulll hyslero­phorus

Baldev R Chhabra*, Meenu Jain & Mandeep K Bhullar

Phytochemical investigation of Mallgifera illdica root bark

J yoti Gupta & Mohd Ali*

R 2

2( HO-0) EtN

2 Et,N'HCI, Cf<,-C~-CH,o-l( o--Q), Three pseudoguaianolides (R1=OH, R2=H; R1=H, R2=OCH, ; R1=OH, R2=OCH,) isolated fro m the ch loro­fo rm extract of P. hysterophorus are reported.

o

Th ree new pent acyc li c trit erpenes, ident ified as olcan­II -one- 13( 18)-ene 1, urs-3-one 2 and 30-dcsmethy l-urs-3-on-20-01 4 and one unknown alicyclic giyc(ls ide. I 0-nonyl-cyclohex -1 2-ene- ] I-glucoside have bee n iso­lated from the root bark of Mal1gijem illdiea culti var Desi in add ition 10 the known compounds B-si lOslerol glycoside, mangiferin and isomangife ri n.

(v i) I NDIAN J CHEM, 38 13 (9) 1999

1099

1104

1106

Chemical characterisation of the lipopolysac­charide from Erwillia lipopolysaccharide

The followi ng plausiblc struct ure for the O-side chain from E. carolovora has been arri ved at.

D-G lep- (l ~2) )-D-Glcp-(l ~3)-D-Glep- ( 1 ~3)-D-Glcp-( 1 ~3) -L-D-Hepp-(J ~3)-L- D-Hepp- ( J ~3)

474 iii

Anup Kumar Datta, Srabani Das,

Nirmolendu Roy* & Sumanta Basu

1 D-Glel' L-D-Hepp

3 i

D-Glep

D-Glep

Notes

Synthesis of (Z)-7-heneicosene and (Z)-7-tricosene via organoboranes - Part V

Raminderjit S BaHn, Ranjit S Dhillon* &

Jasvinder Singh

Photochemical oxidation of 3-methyJcarba­zole: Synthesis of murrayaquinone-A

(E)-2-( I-Octenyl)-l , 3, 2-dioxaborinJncs, preparcd con­venientl y via hydroborat ion of I-octync with BHBr2. SMe2 fo llowed by reacti on with I, 3-propanc diol, upon sequential treatment with the corresponding Grignard reagent at -n oc with 12/M cOH and NaOH at QOC afford the captioned pheromoncs in good yi clds.

i) RMgX,-78 0C

ii) 12/ MeOH R

_ii_i)_N_a_O_H __ •• H13 CsK

H H

4 R = Cn H27 R = C1 5 H31

3-Methylcarbozole 1 undergoes photochemical oxidation in mcthnaol solution to furni sh murrayaq uino ne-A 2, the carbazoloquinone alkaloid isolatcd from MlIrram

ellchreslifolia. The reaction has bcen success full y cx­tended to 3, 6-dimethyl carbazole 3 to yield 3, 6-dimethylcarbazole-! , 4-quinone 4.

o R C~

~ R

B K Chowdhury*, Shailendra Jha, Bibek Ranjan Kar & C Saha

~NA)J H

1 R = H, 3 R = CH3

(vii)

o 2 R = H, 4 R = CH3

INDIAN J CHEM, 38B (9) 1999

1108

1111

CONTENTS

A simple method for the preparation of aryl phenacyl ether in mice\lar medium: Part I

Aryl phenacyl ethers have been prepared from phenol(s ) and phenacyl bromide in the presence o f NEt.l in mi celbr medium.

R3

NEt3 -?-PhCOCH2Sr • PhCOCH2-0 0 R2. +

Micelles

+ H NEt 3 Sr

M NaIIu*, Robinson Selvakumar & M Krishna Pillay

Synthesis of 1-(p-arylidenophenyl)-2-oxo-4-methylpyrido[b ]phenothiazines

V K Pandey* & Seema R Pathak

R1

The title compounds 5 have been prepared starti ng from 7-hydroxy-4- methylcoumarin 1 and p-phenylenediamine.

,,~s~ ~N~NJ:.O

¢ N=CH-R

H

5

1114 Sulfonation of arylamines: Part 9-Solid state The conversion of di-o-RSAS to RSABSA in vo lves N- H synthesis of di-ortho(ring) substituted amino- bond heterolysis in solid state.

1118

benzenesulfonic acids

[~] Di-o-RSAS(1)

Gurdip Siugh*, Inder Pal Singh Kapoor & Jyotsna Singh

Synthesis of pyrido[3,2-a] and indolo[2,3-a]­acridones

S Tharnarai Selvi & P S Mohan*

RSASSA . (4)

A conven ient photol ytic synthesis of titled compnlllllls from 4-hydroxy-2-methylquinoline is reported.

5

(v iii ) INDIAN J CHEM, 3SB(9) 1999

1121

1123

1126

A new synthesis of azetidin-2-ones Diphosphonium tritluoromethanesulphonate 1 PhjP+-O­Ph3P+.2S03CF)-, annelates imines to cis-azetidin-2-ones 5. .

+ + -2 x A1:f>= O+(CF~~O- A13P - 0 - P A13·2SO~F3

1

1 + FCH-PX>H - FO-l:zCXX)P+A13.SO:3CF;+ A13P=O+ CF~~H 2 3

3 +

S S Bari*, M K Sethi & Ashok K Sharma

One pot synthesis of novelS, 11-dioxo-6-methyl-5, 9, 10, 11-tetrahydro-8H-naphth­[2,3: 1,2]pyrrolizine and its 9-acetoxy analogue

4 5a-h

•

5, II-Dioxo:6-methyl-5, 9, 10, II -tetrahydro-8H-naphth­[2,3: 1,2]pyrrolizine and its 9-acetoxy analogue have been prepared in a one-flask procedure by the reaction or L­

proline or 4-hydroxY-L-proline with retluxing AC20 and olefinic dipolarophile I , 4-naphthoquinone.

R Rl Y""\ AC20,~

o

~N""""COOH -------~ I 1,4-naphthoquinone H

G S Gadaginamath*, R R Kavali, S A PatH & A S Shyadligeri

Synthesis of bishydrazones (aldazincs)

N Linganna, K M Lokanatha Rai* &

S Shashikanth

o

Bishydrazones have been prepared by thermolysis or aldehyde hydrazone under pressure in a scaled tube at 120-30°C. The possible mass spectral fragementati oll mode of bishydrazones have also been di scussed.

RCH=NNHCONH2 -------. RCH=N-N=CI

(ix) INDIAN J CHEM, 38B (9) 1999

1129

CONTENTS

Synthesis of some new I, 3-diaryl-5-(2, 3-dihydrobenzoxazole-2-ylidene)-2-thiobarbi­turic acids

R

I, 3-Diaryl-5-(2, 3-dihydrobenzoxazole-2-ylidenel-2-thiobarbituric acids have been synthesized by the con­densation of o-aminophenol with the corresponding 5-bis(methylmercapto)methylene and 5-ethoxymethylene derivative of I , 3-diaryl-2-thiobarbituric acids.

0:: 1-----....

CH(OEtb

jye 'nEt

V K Ahluwalia*, Umashankar Das & Ranjana Sahaya

1132 Microwave induced synthesis of nitrogen- A series of nitrogen mustard derivatives incorporating ~-

1136

mustard derivatives lactam and indole moiety have been synthesised under MWI.

X

NN b>-x -fi- IIH--\S:J R~C

'~N(CIi2CHPl2

"" P PA ~v ~

4a-1

CICOCIi2CV / ~HsCl I ~v

~ Cli2CIi2N(CIi2CIi2Cll2

R-o-b-N-NH X

CIHoQ X%I Cli2N(CIi2CH~Il2

Mazaahir Kidwai*, Rajesh Kumar & Seema Kohli

Synthesis and antimicrobial activity of I, 3, 5-triaryl-IO-benzyl-I, 2, 3, 4, 6, 7, S, 9-octa­hydro-S, S-dimethyl-4, 6-dioxo-2-thioxo-5H, lOH-pyrimido[ 4, 5-b ]quinolines

V K Ahluwalia*, Ranjana Sahay & Umashankar Das

X

X H 0 R

5a-1 6a-1

A convenient one pot synthesis of the titl e compounds hy the condensation of 5, 5-dimethyl-3-benzy larnino-2-cyclohexen-I-one with aryl aldehyde and I , 3-diaryl -2-thiobarbituric acid is reported .

(x) INDIAN.J CHEM, 3SB(9) 1999

1139 Synthesis, characterization and antimicrobial studies of some novel 3-arylazo-7-hydroxy-4-methyIcouJ1"arins

Pratibha Sharma* & Shreeya Pritmani

A novel series of 3-arylazo-7-hydroxy-4-mcthylcoumarin has been synthesized incorporating l -ethoxy-2-arylhydrazono- I, 3-butanones as the precursor foll owed by treatment with resorcinol in acidic medium. Synthe­sized products have been characterized by IR , NMR, mass and elemental analyses. All the compounds have been tested against a number of microorgani sms and most of them found to exhibit remarkable ac tivity.

~:~~ CH3 R5 ~

33 -48

37 RI = CH" R2 = H, R, = H, R4 = H, R, = COOCH,

1143 Xanthone glycoside from rhizome of Acorus Ethanolic extract of the rhi zome of A. calamus yields a

1145

calamus new xdanthone 4, 5, 8-trimethoxyxanthone-2-0-~- D­

glucopyranosyl (I 4 2)-O-~-D-galactopyrono side 1.

Renu Rai*, Aditi Gupta, I R Siddiqui &

J Singh

Chemical investigation of the Marine sponge Axinella telluidigitata

N Srinivasa Reddy, P Ramesh,

T Prabhakara Rao, J Venkateswara Rao

& Y Venkateswarlu*

OWe OWe

$1 0 1 ~ ~OH ~ .0 0

OH

OWe 0 I,~OH V-j-LOH J-()

Four pyrrole based alkaloids 1-4 and a A-nor stero id 5 have been isolated from the sponge Axinella lenuidig iIa/a and are characterized from their spectral studies. Com­pounds 1-4 exhibit mild toxicity against brine shrimp Artemia salina.

o

~H RA~~NI H 0

1 R = H 2 R= Sr

(x i) INDIAN J CHEM, 38B (9) 1999

1148

CONTENTS

Chemical examination of Citrullus colocynth is roots

Three new compounds besides four known compounds have been isolated from the roots of C. coloc)'lllhis and characterised as tridecyl-2-methyl-19-ene-tri acontanote I, heptadecyl trieicosanoate 2, nonaeicosanol 3, dotriac­ontanol 4, l-hentriacontanol 5, dotriacontanoic acid 6, and tetraeicosanoic acid 7 using JR, 'H NMR, DC NMR and mass spectral data_

M Manoranjani, Shrilakshmi Kotra & B KMehta*

o cu-II I ".j

H~- (CHV 12-0-C-CH- (CI-i3l16- CH= CH- (CH2lg-- CH3

o Cu­II I ".j

~- (CH2l16-0-C-CH- (CH3l a>- CH3

2

~-(CHV27-CH~H

3

Authors for correspondence are indicated by (*)

(xii) INDIAN J CHEM, 38B(9) 1999