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  • Title: Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones.
    Author: Bruno G, Costantino L, Curinga C, Maccari R, Monforte F, Nicoló F, Ottanà R, Vigorita MG.
    Journal: Bioorg Med Chem; 2002 Apr; 10(4):1077-84. PubMed ID: 11836118.
    Abstract:
    Several (Z)-5-arylidene-2,4-thiazolidinediones were synthesized and tested as aldose reductase inhibitors (ARIs). The most active of the N-unsubstituted derivatives (2) exerted the same inhibitory activity of Sorbinil. The introduction of an acetic side chain on N-3 of the thiazolidinedione moiety led to a marked increase in lending inhibitory activity, conducting to the discovery of a very potent ARI (4c), whose activity level (IC50=0.13 microM) was in the same range of Tolrestat. Moreover, the corresponding methyl esters (3), devoid of any acidic functionality, showed appreciable inhibitory activity similar to that of the N-unsubstituted compounds. It was also found that the substitution pattern on the 5-benzylidene moiety markedly influenced the activity of N-unsubstituted 2,4-thiazolidinediones 2, compounds with substituents at the meta position being generally more effective than the para-substituted ones; however, this SAR was not evidenced in acetates 3 and acids 4.
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