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

Kavitha, C. V. and Basappa and Nanjunda Swamy, S. and Mantelingu, K. and Doreswamy, S. and Sridhar, M. A. and Shashidhara Prasad, J. and Rangappa, K. S. (2006) Synthesis of new bioactive venlafaxine analogs: novel thiazolidin-4-ones as antimicrobials. Bioorganic & Medicinal Chemistry, 14 (7). 2290 - 2299. ISSN 1464-3391

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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.

Item Type: Article
Uncontrolled Keywords: Thiazolidinone, Crystal structure, Venlafaxine analogs, Antimicrobials
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: LA manjunath user
Date Deposited: 26 Aug 2019 05:33
Last Modified: 11 Dec 2019 11:17

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