Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

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VOL. 46B

NUMBER 1

JANUARY 2007

CONTENTS

Papers

 

 

 

115

Synthesis and bronchodilatory activity of new

4-aryl-3,5-bis-(2-chlorophenyl)carbamoyl-2,6

-dimethyl-1,4-dihydropyridines and their

1-substituted analogues

 

IPC: Int.Cl.8 C07C

New 1,4-DHPs have been prepared by rapid synthetic methods, characterized and their yields and reaction times compared. They have been screened for their bronchodilatory activity and the results are reported.

 

 

 

 

 

 

 

T Suresh, S K Swamy & V M Reddy*

 

 

 

 

 

 

 

122

Synthesis of substituted and unsubstituted 5-(1,3-diaryl-1-oxopropyl)pyrimidine(1H, 3H, 5H)-2,4,6-triones

 

IPC: Int.Cl.8 C07D

Reactions of 1,3-diaryl-2-propene-1-ones give the correspond­ing 5-(1,3-diaryl-1-oxopropyl)pyrimidine (1H,3H,5H)-2,4,6-triones with barbituric acid under refluxing condition without using any catalyst.

 

 

 

 

 

 

 

M Giasuddin Ahmed*, Syeda Asghari Ahmed,

S Mosaddeq Ahmed, Tazin Sultana &

Md Khabir Uddin

 

 

 

 

 

 

 

 

 

 

 

 

126

Synthesis of amide derivatives of quinolone and their antimicrobial studies

 

IPC: Int.Cl.8 C07C

A series of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[chloro/1-piperazinyl/4-methyl-1-piperazinyl/4-ethyl-1-piper­azinyl/4-hydroxyethyl-1-piperazinyl/imidazolyl/morpholinyl]-3[N-(substi­tuted phenyl amino) carbo-nyl]quinoline 5a-j-11a-j have been prepared by using substituted arylamine at C-3 position and 1-piperazine/4-methyl-1-piperazine/4-ethyl-1-piperazine/4-hydroxyethyl-1-piperazine/imidazole/morpholine at C-7 position of newly synthesized quinolone 3. Biological profile like antibacterial activity against four different strain viz. S. aureus and B. subtilis (gram-positive bacteria) and E. coli and P. aeruginosa (gram-negative bacteria) and C. albicans (fungi) by cup plate method have been studied.

 

 

 

 

 

 

 

N B Patel*, A L Patel & H I Chauhan

 

 

 

 

 

 

135

Synthesis of some pyrazino, pyrimido and mercaptopyrimido annelated carbazoles using 2-hydroxymethylene-1-oxo-1,2,3,4-tetrahydrocarbazoles

 

 

 

IPC: Int.Cl.8 C07D

 

 

 

 

 

V Sangeetha & K J Rajendra Prasad*

 

 

 

 

 

 

 

 

 

 

 

 

 

141

Polymorphism in hydrazonium salt of

3,5-pyrazoledicarboxylic acid

 

 

IPC: Int.Cl.8 C07C

Two polymorphic structures of hydrazonium monobasic salts of 3,5-pyrazoledicarboxylic acid are described. In both instances, one-dimensional infinite chains formed by acid molecules through O–H∙∙∙O hydrogen bonding (1.68 Å ,177.1°; 1.71 Å ,169°) are inter-linked by hydrazonium dications to form two-dimensional sheets. The subtle structural difference between the two forms arises in the packing of hydrazonium dications. In form A, the hydrazonium dications are relatively close packed compared to those in form B. The closest N…..N distance between two hydrazonium dications of inversion related layers in form A is 2.03 Å whereas the closest N…..N distance between two similar hydrazonium dications (disordered) is 4.89 Å for form B. This account for the higher packing fraction (78% vs 76.2%) of form A compared to form B.

 

 

 

 

 

 

 

 

 

V S Senthil Kumar, T Premkumar,

Nigam P Rath & S Govindarajan*

 

 

 

 

 

 

 

148

Synthesis and antimicrobial activity of 5-amino-2,7-diaryl-6-cyano-3-isonicotinamido thiazolo[4,5-b]-2,3,4,7-tetrahydropyridines, 2,7-diaryl-6-cyano-3-iso­nico­tin­amido thiazolo[4,5-b]-2,3,4,5,6,7-hexahydro­pyrid-5-ones, 2,7-diaryl-5-amino-3-isonicotinamido thiazolo[4,5-d][1,3]thiazines and 2,6-diaryl-3-isonico­tinamido thiazolo[4,5-c] pyrazolines

 

IPC: Int.Cl.8 C07D

5-Amino-2,7-diaryl-6-cyano-3-isonicotinamido thiazolo[4,5-b]-2,3,4,7-tetrahydropyridines and 2,7-diaryl-6-cyano-3-iso­nico­tinamido thiazolo[4,5-b]-2,3,4,5,6,7-hexahydropyrid-5-ones have been prepared by Michael addition between  a,b-unsaturated ketones and malononitrile/ethyl cyanoacetate in the presence of excess ammonium acetate. 2,7-Diaryl-5-amino-3-isonicotinamido thiazolo[4,5-d][1,3]thiazines and 2,6-diaryl-3-isonicotinamido thiazolo[4,5-c]pyrazolines have been prepared by cyclocondensa­tion of a,b-unsaturated ketones with thiourea/hydrazine hydrate, respectively. The antimicrobial activity of the representative samples are assayed against bacteria sE. coli, B. subtilis, S. aureus and fungi A. niger, P. oryzae and F. oxysporum at 100 mg/mL concentration.

 

 

 

 

Mukhtar Hussain Khan

 

 

 

 

 

 

 

 

 

 

 

 

 

154

Recyclable polymer bound Pd(0) phosphine catalyst for effecting sp2-sp2 and sp2-sp carbon-carbon coupling reactions in aqueous medium

IPC: Int.Cl.8 C07D

Aqueous Heck type coupling reactions between aryl iodides and terminal alkenes or alkynes have been effected in good yields using a recyclable catalyst system that consists of poly(N-isopropyl acrylamide) bound Pd(0) phosphine and an anionic surfactant, potassium lauryl sulphate.

 

 

 

 

Nirmal Koshti*, Bharat Parab & Shubhangi Naik

 

 

 

 

 

 

 

160

Conformational studies of some N-acyl-t(3)-isopropyl-r(2),c(6)-bis(2¢-furyl)piperidin-4-ones

 

IPC: Int.Cl.8 C07D

The high resolution 1H and 13C NMR spectra of four N-acyl-t(3)-isopropyl-r(2),c(6)-bis(2¢-furyl)piperidin-4-ones 1-4 have been recorded at various temperatures and analysed.

 

 

 

 

A Manimekalai*, K Selvaraju & T Maruthavanan

 

 

 

 

 

 

 

170

Alternate routes for the synthesis of ibuprofen piconol

 

IPC: Int.Cl.8 C07D

New, improved and alternate methods for the synthesis of ibuprofen piconol from ibuprofen and pyridine-2-methanol have been demonstrated with different carboxyl activating groups

 

 

 

 

 

C M Haricharan Raju, C Vijay Anand, P K Dubey &

Palle V R Acharyulu*

 

 

 

 

 

 

 

 

 

 

 

 

173

Two new terpenes from the lichen Parmelia perlata

 

 

 

IPC: Int.Cl.8 C07D

The lichen Parmelia perlata an important drug used in Indian systems of medicine has yielded a new lanost-2-en type triterpene, named parmelanostene and a new labdane type diterpenoid, named permelabdone, identified on the basis of spectroscopic studies as 29, 30-nordimethyl-lanost-2-en 1 and 2¢-methoxy­phenyl-19-[4a,8b,10b-trimethyl-9-(13-methyl butyl)-deca­hydro­napthalen-4-yl]-20-methoxy­enzoate 2, respecti­vely. The compounds showed antibacterial activity against S. aureus and E. coli.

 

 

 

 

S Tarique Abdullah, Hinna Hamid, Mohammed Ali,

S H Ansari & M Sarwar Alam*

 

 

 

 

 

 

 

177

QSAR studies of cytotoxic acridine 5,7-diones : A comparative study using P-VSA descriptors and topological descriptors

 

IPC: Int.Cl.8 C07D

A comparative QSAR analysis of a series of cytotoxic acridine 5,7-diones was performed using topological descriptors and a novel set of P-VSA descriptors.

 

 

 

N S Hari Narayana Moorthy, C Karthikeyan &

Piyush Trivedi*

 

 

 

 

 

 

 

185

Synthesis and primary cytotoxicity evaluation of new diaryltriazenes

A series of triazenes derived from 5-(4-aminophenyl)-2,4-dihydro–4-substituted-3H-1,2,4-triazole-3-thiones 1a-c, amino­glutethimide or paraaminobenzoic acid have been synthesized for in vitro anticancer properties.

 

 

 

 

 

S Unsalan & S Rollas*

 

 

 

 

 

 

 

 

 

 

 

 

 

192

Phototransformation of 16a,17a-epoxy-3b-hydroxy­pregn-5-ene-20-one to 3b-hydroxy-pregn-5-ene-16,20-dione

 

IPC: Int.Cl.8 C07C

UV irradiation of 16a,17a-epoxy-3b-hydroxy-pregn-5-ene-20-one 5 in a variety of solvents (benzene, acetonitrile, methanol) and in the presence of triethylamine, pyrex glass reactor, leads to the formation of 3b-hydroxypregn-5-ene-16,20-dione 6.

 

 

 

 

 

 

 

N Kumar Girdhar, Abdul Faruk, K Avtar Suri &

M P S Ishar*

 

 

 

 

 

 

 

195

Microwave accelerated synthesis of novel spiro heterocycles

 

IPC: Int.Cl.8 C07C

A quick and efficient method for the synthesis of variety of spiro heterocycles containing fused triazoles, thiazetidines, oxoazetidines, diazetidines and thiadiazoles moiety by microwave technique as well as by classical thermal method has been described.

 

 

 

 

 

 

Vijay V Dabholkar* & Sagar D Parab

 

 

 

 

 

 

 

 

 

 

Notes

 

 

 

201

Synthesis of N-(3,5-dimethyl-4-hydroxybenzyl)-N-tosyl-3,4-dimethoxybenzyl amine

 

IPC: Int.Cl.8 A61K

Reaction of 4-benzyloxy-3,5-dimethyl benzyl bromide 4 and N-tosyl-3,4-dimethoxy benzyl amine 5 gave N-(4′-benzyloxy -3′,5′-dimethylbenzyl)-N-tosyl-3,4-dimethoxybenzyl amine 6. The obtained product on debenzylation gave N-(3′,5′-dimethyl-4′-hydroxybenzyl)-N-tosyl-3,4-dimethoxy benzyl amine 7 in 94% yield, which is key intermediate in the synthesis of isoindolines.

 

 

 

 

 

 

 

 

 

B China Raju, Parvathi Neelakantan &

U T Bhalerao*

 

 

 

 

 

 

 

204

Silica supported chromium trioxide: Microwave pro­moted oxidative ring closure of a-cyano-b-thioen­amino­nes to isothiazoles

 

IPC: Int.Cl.8 C07D

Silica supported chromium trioxide is found to be an excellent reagent for oxidative ring closure of a-cyano-b-thioenaminones to isothiazoles in dichloromethane at room temperature or in dry media under microwave irradiation.

 

 

 

 

 

 

Manisha Mishra & Kumar K Mahalanabis*

 

 

 

 

 

 

 

 

 

 

 

 

 

 

207

Microwave assisted synthesis of N-(3-aryl-1,8-naphthy­ridin-2-yl)phthalimides under solvent-free conditions

 

IPC: Int.Cl.8 C07C

A simple, rapid and efficient method for the synthesis of N-(3-aryl-1,8-naphthyridin-2-yl)phthalimides 3 in solvent-free conditions under microwave irradiation has been described.

 

 

 

 

 

 

K Mogilaiah* & B Sakram

 

 

 

 

 

 

 

210

Microwave-assisted facile synthesis of a new class of asymmetrical diheteroarylmethanes bearing imidazo­pyridine moieties under solvent-free condition

 

IPC: Int.Cl.8 C07D

A useful approach to diheteroarylmethanes bearing imidazopyridine moieties is described.

 

 

 

 

 

 

Guiyun Duan, Yawei Sun, Junzhi Liu,

Guilong Zhao, Datong Zhang & Jianwu Wang*

 

 

 

 

 

 

 

213

A novel synthesis of spiroisoxazoles via 1,3-dipolar cyclo­addition of nitrile oxide to 6-arylidene-6,7,8,9-tetra­hydro­benzocyclohepten-5-one

 

IPC: Int.Cl.8 A61K

Synthesis of a series of spiroisoxazole derivatives have been accomplished in good yield by regioselective 1,3-dipolar cycloaddition of nitrile oxide to 6-arylidene-3-methyl-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one. The antimicrobial activity of these compounds have been carried out.

 

 

 

 

 

 

 

Peesapati Venkateswarlu* &

Nageswara Rao Vasireddy

 

 

 

 

 

 

 

 

 

 

 

 

 

216

Synthesis of novel 1,2,4-oxadiazole heterocyclic compounds contain 2-H-pyranopyridine-2-one moiety and related compounds

 

 

IPC: Int.Cl.8 C07D

Ethyl 5-methyl-6-cyano-7-hydroxy-2-oxo-2H-pyrano [2, 3-b] pyridine-3-carboxylate 1 and ethyl 5-methyl-6-cyano-7-chloro-2-oxo-2H-pyrano [2, 3-b] pyridine-3-carboxylate 2 are treated with aqueous ammonia solution to afford 2H-pyrano[2,3-b] pyridine-3-carboxamide 3a-b, which are converted to 6-carboxamidoxime2H-pyrano[2,3-b]pyridine-3-carboxamide 4a-b and hydroxylamine on refluxing ethanol. Carboxamidoximes are treated with various acid chlorides to obtain 1,2,4-oxadiazole derivatives 5, 6a-c. The compound 3a was reacted with triethyl orthoformate to give 4-amino-5-methyl pyrano [3", 2':5, 6] pyrido[2,3-d] pyrimidine7-carboximde 7, 4a is allowed to reacted N, N-dimethyl formamide dimethyl acetal under reflux N-(6-carbonyl-4-methyl-7-oxo-1,7-dihydropyrano[2,3-b]pyrazolo[4,3-e] yridine-3-yl) methanamide 8.

 

 

 

 

 

N Vasanth Kumar & Uday C Mashelker*

 

 

 

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

Int.Cl8.: International Classification, 8th Edition, 2006