• A novel synthesis and preliminary in vitro cytotoxic evaluation of dihydropyrimidine-2,4(1H,3H)-dione derivatives

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      https://www.ias.ac.in/article/fulltext/jcsc/129/02/0249-0258

    • Keywords

       

      Triflic anhydride; Boc anhydride; Negishi coupling; acid-amine coupling; cyclization reaction; cytotoxicity; MCF-7.

    • Abstract

       

      We report the synthesis and characterization of four new compounds: 6-(2-(1H-inden-2-yl) phenyl)-3-(2-morpholinoethyl)dihydropyrimidine-2,4(1H,3H)-dione (13a), 6-(2-(1H-inden-2-yl)phenyl)-3-(2-(pyrrolidin-1-yl)ethyl)dihydropyrimidine-2,4(1H,3H)-dione (13b), 6-(2-(1H-inden-2-yl)phenyl)-3-phenethyldihydropyrimidine-2,4(1H,3H)-dione (13c) and 3-(3-(1H-imidazol-1-yl)propyl)-6-(2-(1H-inden-2-yl)phenyl) dihydropyrimidine-2,4(1H,3H)-dione (13d). A series of dihydropyrimidine-2,4(1H, 3H)-dione moieties was derived from methyl 3-amino-3-(2-chlorophenyl)propanoate precursor in a multi-step synthesis. Acid-aminecoupling of 3-(2-(1H-inden-2-yl)phenyl)-3-((tert-butoxycarbonyl)amino)propanoic acid with a series of amine derivatives under mild reaction conditions led to form the corresponding dihydropyrimidine-2,4(1H, 3H)- dione derivatives via de-Boc and cyclization reaction in modest yield. Spectroscopic (¹H, ¹³C NMR, and Mass) and analytical techniques have been used to identify and confirm the structure of the products.

    • Author Affiliations

       

      V UDAYAKUMAR1 J GOWSIKA2 A PANDURANGAN1

      1. Department of Chemistry, Anna University, Guindy, Chennai 600 025, India
      2. Department of Chemistry, Pachaiyappa’s College, University of Madras, Chennai 600 030, India
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