Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

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VOL. 47B

NUMBER 5

MAY 2008

CONTENTS

Advances in Contemporary Research

 

 

 

721

Retrometabolism based drug targeting- soft drug approach

 

A soft drug is pharmacologically active as such and it undergoes a predictable and controllable metabolism to non-toxic and inactive metabolites.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

C S Ramaa*, Rhea Mohan, A S Mundada &

V J Kadam

 

 

 

 

 

Papers

 

 

 

734

Double Michael addition reactions of methyl-3-aryl-2-(Z-styrylsulfonyl)-acrylate

 

The double Michael addition of active methylene compounds, viz., dimethyl malonate, ethyl cyanoacetate and malo­no­nitrile to methyl-3-aryl-2-(Z-styrylsulfonyl)acrylate is described.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

V Padmavathi*, K Sudheer & A Padmaja

 

 

 

 

 

 

 

 

740

Biologically active hydroximoyl chlorides as anti­fungal agents

An approach towards the synthesis ofchlorooximes as novel antifungal agents is reported.

 

 

 

 

 

 

 

 

 

 

 

Tabasum Ismail, Syed Shafi, Parvinder Pal Singh,

Naveed Ahmed Qazi, Sanghapal D Sawant, Intzar Ali,

Inshad Ali Khan, H M S Kumar*, Ghulam Nabi Qazi &

M Sarwar Alam

 

 

 

 

 

 

 

748

Synthesis of some new 10H-pyrido[3,2-b][1,4] benzo­thiazine and their ribofuranosides as pos­sible chemotherapeutic agents

 

N-(2´, 3´, 5´-tri-O-benzoyl-b-d-ribofuranosyl)-8-chloro-7-methyl/7,9-dimethyl/ 8-chloro-9-methyl-3-nitro pyrido [3,2-b][1, 4]benzothiazine have been synthesized by the treatment of 10H-8-chloro-7-methyl/ 7,9-dimethyl/8-chloro-9-methyl-3-nitropyrido[3,2-b][1,4] benzothiazines. The antimicrobial activities of all these derivatives have been accomplished.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Naresh Kumar & Ashok K Yadav*

 

 

 

 

 

 

 

 

 

 

753

Synthesis of novel naphtho[2,1-b]furo[3,2-b]pyri­dine derivatives as potential antimicrobial agents

 

The compounds 4a,b undergo Friedlander cyclization on treatment with active methylene compounds, and produce title compounds 5a,b, 6a,b and 7a,b. Some other routes for the synthesis of various derivatives of this new heterocycle have been investigated. All the newly synthesized compounds are characterized by elemental analysis, spectral studies, and have been evaluated for antimicrobial activity.

 

 

 

 

 

 

 

 

 

 

 

D Ramesh, C Chandrashekhar & V P Vaidya*

 

 

 

 

 

 

 

759

Synthesis of some 7-methyl-3-(2-oxo-2H-chromen-3-yl)thiazolo[3,2-a]pyrimidin-5-ones

 

Reaction of 3-(2-amino-4-thiazolyl)-coumarins with ethyl acetoacetate in a mixture of PPA and POCl3 gave 7-methyl-3-(2-oxo-2H-chromen-3-yl)thiazolo[3,2-a]-pyrimidin-5-ones in a single step. 

 

 

 

 

 

 

 

 

 

 

 

P  Vijaya kumar, K Manoher Reddy &

V  Rajeswar Rao*

 

 

 

 

 

Notes

 

 

 

764

Synthesis of some novel 1, 2, 4-triazolo [4, 3-a] 2H-pyrano [3, 2-e] pyridine derivatives

 

The compound 2 is prepared by reacting ethyl-5-methyl-6-cyano-7-chloro-2-oxo-2H-pyrano[2,3-b]pyridine-3-carbo­xy­late 1 with hydrazine hydrate at room temperature furnishes 2 with good yield. Condensation of 2 with acids results in the formation of 1-substituted 2H-pyrano [3,2-e][1,2,4]triazolo[4,3-a]pyridine 3, further the hydrazine derivative 2 is transformed to 1-aryl- 2H-pyrano[3,2-e][1,2,4]triazolo[4,3-a]pyridine 4. These compounds are expected to have as better antihypertensive activity.

 

 

 

 

N Vasanth Kumar & Uday C Mashelkar*

 

 

 

 

 

 

 

767

New tandem reactions for the construction of heterocycles via dianion strategy

 

The reaction of chiral and achiral salen ditopic ligands with sodium in dry isopropanol generates remote O,O-dianions. The dianions thus generated in situ are trapped by suitable phosphorus dielectrophiles to yield 2-oxo and 2-thioxo-1,3,7-dioxazaphospha-decines and 2-oxo and 2-thioxo-1,3,7,10-dioxadiazaphospha-tridecines in moderate to good overall yield. The products are characterized by elemental and spectral (IR, 1H, 13C, 31P NMR and Mass) studies.

 

 

 

 

 

M S Singh*, Pratibha Singh & Pallavi Singh

 

 

 

 

 

 

 

773

Two new neolignan glycosides from Pteris multifida poir

7S, 8S)-Δ7-2,9-dihydroxy-5-methoxy-7,3-dioxy-8, 4-neo­lignan-4-O-β-d-apiofuranosyl-(1→6)-β-d gluco­pyranoside and (7S, 8S)-Δ7-2,9,9-trihydroxy- 7,3-dioxy-8,4-neolignan-4-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside, named as multifidoside A and B, have been isolated from the roots of Pteris multifida Poir.

 

 

 

 

 

 

R1=H  R2=OMe                   2  R1=OH  R2=H

 

 

 

 

 

 

 

Zheng Xu-Dong*, Hu Hao-Bin &Hu Huai-Sheng

 

 

 

 

 

 

 

778

Reaction of ethyl cyanoacetate with benzal-4-acetylanilines: An unexpected result

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Anjali Sidhu & Mangat Rai*

 

 

 

 

 

 

 

781

Synthesis, antimicrobial and mosquito larvicidal activity of N-protected amino acid/peptide isoxazoles

A series of N-protected amino acid/peptide isoxazoles 4-12 and 15-16 have been synthesized and the antimicrobial activity  evaluated against three gram positive, three gram negative bacteria and five plant pathogenic fungi. Mosquito larvicidal activity of the newly synthesized compounds is also studied against fourth instar larve Culex quinq­uefasciatus.

 

 

 

 

 

E Rajanarendar*, G Mohan, E Kalyan Rao,

A Siva Rami Reddy, B Praveen & M Srinivasa Rao

 

 

 

 

 

 

787

Synthesis and nematicidal activity of 2-(1H-benzo [d]imidazol-2-ylmethyl)-4-aryl-1-thia-4-azaspiro­[4.5] decan-3-one

 

A series of N-cyclohexylidene-N-phenylamines 3 are prepared by the condensation of cyclohexanone 1 with aryl amine 2, subsequent treatment of 3 with thiomalic acid gave the corresponding 2-(3-oxo-4-aryl-1-thia-4-azas­piro­[4.5]­dec-2-yl)acetic acid 4, which on reaction with o-phenylene­diamine gave 2-(1H-benzo[d]imidazol-2-ylmethyl)-4-aryl-1-thia-4-azaspiro[4.5]decan-3-one 5. The compounds are characterized by IR, 1H NMR, MS and elemental analyses.  The antibacterial, antifungal and nematicidal activities of the compounds are also evaluated.

 

 

 

 

 

 

A Srinivas, A Nagaraj & Ch Sanjeeva Reddy*

 

 

 

 

 

 

 

 

 

 

792

A novel and environmental friendly, one step synthesis of 2,6-diamino-4-phenyl pyrimidine-5-carbonitrile using potassium carbonate in water

A green, simple and environmentally friendly approach towards one-step synthesis of 2,6-diamino-4-phenyl pyrimidine-5-carbonitrile by three-component condensation of aromatic aldehydes, malononitrile and guanidine hydrochloride in aqueous medium using potassium carbonate and in presence of tetrabutyl ammonium bromide has been reported.

 

 

 

 

 

M B Deshmukh*,  P V Anbhule, S D Jadhav,

S S Jagtap, D R  Patil, S M Salunkhe &

S A Sankpal

 

 

 

 

 

Authors for correspondence are indicated by (*)