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Synthesis, Characterization and Cytotoxic Studies of New Thiazolidinones

Author

Listed:
  • Shafia Mir
  • Masrat Jan
  • Praveen Kumar

    (Department of Chemistry, OPJS University, Rajasthan, India)

  • Ayaz Mahmood Dar

    (Department of Chemistry GDC Kulgam, University of Kashmir, Jammu and Kashmir, India)

Abstract

A new series of substituted aromatic thiazolidinones [1-4]were synthesized by the reaction of acetophenone and its derivatives [5-8]with hydrazine hydrate and merceptoacetic acid in absolute ethanol in one pot manner. The striking feature of this reaction is the formation of hydrazone in situ which in turn undergoes the cyclization with mercepto acetic acid, leading to the formation of new thiazolidinones. Thus, the thiazolidinone ring closes at carbonyl carbon, by the attack of sulfur of mercaptoacetic acid moiety, preferentially from the front (β, axial) so that the nitrogen has an equatorial orientation (α, equatorial) to avoid steric repulsion, giving minimum steric hindrance. The new compounds were characterized by spectral (IR, 1H NMR,13C NMR, MS) and analytical methods. The new compounds were screened for cytotoxicity (MTT assay) as well as genotoxicity (Comet assay) studies against different cancer cell lines, during which the new compounds depicted potential anticancer behaviour.

Suggested Citation

  • Shafia Mir & Masrat Jan & Praveen Kumar & Ayaz Mahmood Dar, 2018. "Synthesis, Characterization and Cytotoxic Studies of New Thiazolidinones," Organic & Medicinal Chemistry International Journal, Juniper Publishers Inc., vol. 8(1), pages 17-22, October.
    • Handle: RePEc:adp:jomcij:v:8:y:2018:i:1:p:17-22
    DOI: 10.19080/OMCIJ.2018.08.555730
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