Synthesis of new bioactive venlafaxine analogs: novel thiazolidin-4-ones as antimicrobials.

Abstract:

:A one-pot, three-component, microwave irradiated and conventional solution-phase synthesis of bioactive venlafaxine analogs such as 2,3-disubstituted-1,3-thiazolidin-4-ones 3a-j under mild conditions and their characterization are reported. The novel thiazolidin-4-ones, 3-(2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl)-2-phenyl-thiazolidin-4-one 3a, 2-(2,6-difluorophenyl)-3-(2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl)thiazolidin-4-one 3c, and 2-(furan-2-yl)-3-(2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl)thiazolidin-4-one 3i, were characterized by the single crystal X-ray diffraction method. The cyclohexane ring of all the three molecules is in chair conformation. All the synthesized compounds were screened for their efficacy as antimicrobials in vitro by the disk diffusion and microdilution method against pathogenic strains such as Bacillus subtilis, Escherichia coli, Pseudomonas fluorescens, Xanthomonas campestris pvs, Xanthomonas oryzae, Aspergillus niger, Aspergillus flavus, Fusarium oxysporum, Trichoderma species, and Fusarium monaliforme species. Among these compounds 3c, 3j, 3g, 3d, and 3e showed potent antimicrobial activity, when compared to standard drugs.

journal_name

Bioorg Med Chem

authors

Kavitha CV,Basappa,Swamy SN,Mantelingu K,Doreswamy S,Sridhar MA,Shashidhara Prasad J,Rangappa KS

doi

10.1016/j.bmc.2005.11.017

subject

Has Abstract

pub_date

2006-04-01 00:00:00

pages

2290-9

issue

7

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(05)01074-6

journal_volume

14

pub_type

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