Synthesis and Anti-microbial Activities of Thiazolidin-4-one Derivatives

Kanchugarakoppal S. Rangappa 1Kamaiah Jayalakshmi 1Chandagirikoppal V. Kavitha 1Siddaiah Chandra Nayaka 2Basappa Basappa 1Hirihalli C. Devarajegowda 3Javaregowda Shashidhara Prasad 3

1. University of Mysore (UOM), Manasagangothri, Mysore, Bangalore 570005, India
2. Department of Studies in Applied Botany, Seed Pathology and Biotechnology, Mysore 570006, India
3. University of Mysore Physics, Manasagangotri, Mysore 570006, India

Abstract

Development of novel therapeutics for the treatment of microbial infection has become a clinical imperative. Synthetic combinatorial libraries made up of hundreds to millions of small organic molecules have been successfully developed and used to discover new antimicrobial leads. In this connection, a series of thiazolidin-4-one derivatives are synthesized by one pot, three-component condensation of amine, aldehyde and thioglycolic acid using γ-ferrite as a catalyst, an effective adsorbent for water molecule (dehydrating agent). The synthesized compounds were characterized by spectral and elemental analyses. The anti-microbial studies of the above mentioned nucleus gave a concordant inhibitory results, where the polycyclic aromatics and the electron withdrawing substituents at both the 3rd and 4th position of the phenyl group. Antimicrobial data of thiazolidin-4-ones against mycotoxigenic isolates of F. verticillioides, A. alternata, A. flavus, A. ochraceous and p. chrysogenum and bacterial isolates of X. oryzae Pv oryzae, C. michigensis Pv michigensis, E. coli, S. aureus and B. subtilis indicate that all the compounds show moderate to strong inhibitory activities compared to streptomycin and nystatin. The X-ray crystallographic details of the compound 2-(4-chlorophenyl)-3-(4-phthalimide)-1,3- thiazolidin-4-one 4a reveals that it crystallizes in monoclicnic system, the space group is p21/a .T=293(2) K and the final R factor is 6.6%.

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Presentation: oral at 18th Conference on Physical Organic Chemistry, Symposium 2, by Kanchugarakoppal S. Rangappa
See On-line Journal of 18th Conference on Physical Organic Chemistry

Submitted: 2006-07-17 18:05
Revised:   2009-06-07 00:44
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