Victor Facchinetti, Felipe A. Guimarães, M. D. Souza
Jul 1, 2015
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Journal
Journal of Heterocyclic Chemistry
Abstract
A series of ethyl (substituted)phenyl-4-oxothiazolidin-3-yl)-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylates (7a, 7b, 7c, 7d, 7e, 7f, 7g) has been prepared from reactions between aminoquinolones 6 with arenealdehydes and mercaptoacetic acid. The critical intermediates, 6a and 6b, were obtained from appropriate amines by a sequence of steps involving (i) reaction with diethylethoxymethylenemalonate, (ii) thermal cyclization in diphenyl ether, (iii) ethylation and (iv) Pd/C catalyzed reduction. New compounds 7a, 7b, 7c, 7d, 7e, 7f, 7g were fully identified and characterized by NMR (1H and 13C) and specifically for 7d by X-ray crystallography. Compounds 7b, 7c, 7d, 7e, 7f were found not to exhibit activity at 10 uM concentrations against gastric ascitis (AGP-01), gastric adenocarcinoma kind intestinal (ACP-02), colon (HCT-116) and murine melanome (B16F10) cancer cells. However, none exhibited cytotoxicity against normal cells human fibroblast (MRC-5), murine fibroblast (NIH3T3) and normal human melanocyte (Melan-A).