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C-3 Alkyl /Arylalkyl-2,3-dideoxy hex-2-enopyranosides as Antitubercular Agents: Synthesis, Biological Evaluation and QSAR Study

IR@CDRI: CSIR-Central Drug Research Institute, Lucknow


Field	Value

Creator	Saquib, Mohammad Gupta, M K Sagar, Ram Prabhakar, Y S Shaw, A K Kumar, Rishi Maulik, P R Gaikwad, Anil Sinha, Sudhir Srivastava, A K Chaturvedi, Vinita Srivastava, Ranjana Srivastava, B S

Date	2008-02-25T05:26:41Z 2008-02-25T05:26:41Z 2007

Identifier	Journal of Medicinal Chemistry (2007), 50, 2492 http://hdl.handle.net/123456789/88

Description	A series of C-3 alkyl and arylalky 2,3-dideoxy hex-2-enopyranoside derivatives were synthesized by Morita-Baylis-Hillman reaction using enulosides 4, 5 and 6 and various aliphatic and aromatic aldehydes. The compounds were evaluated in vitro for the complete inhibition of growth of Mycobacterium tuberculosis H37Rv. They exhibited moderate to good activity in the range of 25-1.56 µg/mL. Among these, 4d, 4h, 5c and 4hr showed activity at minimum inhibitory concentrations, 3.12, 6.25, 1.56 and 1.56µg/mL, respectively. These compounds were safe against cytotoxicity in VERO cell line and mouse macrophage cell line J 744A.1. A QSAR analysis by CP-MLR with alignment-free 3D-descriptors indicated the relevance of structure space comparable to the minimum energy conformation (from conformational analysis) of 5c to the activity. The study indicates that the compounds attaining conformational space 5c and reflecting some symmetry, minimum eccentricity and closely placed geometric and electronegativity centers therein are favorable for activity.

Format	394356 bytes application/pdf

Language	en

Subject	Antitubercular activity Morita-Baylis-Hillman reaction C-3 alkyl /arylalkyl-2,3-dideoxy hex-2-enopyranosides QSAR study CP-MLR alignment-free 3D-descriptors DRAGON descriptors

Title	C-3 Alkyl /Arylalkyl-2,3-dideoxy hex-2-enopyranosides as Antitubercular Agents: Synthesis, Biological Evaluation and QSAR Study

Type	Article