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Synthesis of Thiazolopyrimidines via Annulation of N ‐(4,6‐Diaryl‐2‐thioxo‐1,2,3,6‐tetrahydropyrimidin‐4‐yl)phenyl)aryl‐sulfonamides
Author(s) -
Bahekar Sandeep P.,
Chandak Hemant S
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702785
Subject(s) - sulfonamide , thiourea , chemistry , aryl , acetic acid , annulation , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , alkyl
A series of 5,7‐diaryl‐5 H ‐thiazolo[3, 2‐a]pyrimidin‐3(2 H )‐ones (4 a‐4 r) bearing sulfonamide scaffold have been synthesized by cyclocondensation of bromoacetic acid and N ‐(4,6‐diaryl‐2‐thioxo‐1,2,3,6‐tetrahydropyrimidin‐4‐yl)phenyl)aryl‐sulfonamides (3 a‐3ab) . Compounds 3 a‐3ab have been synthesized by cyclocondensation of sulfonamide chalcones (1) and thiourea. Acetic acid: acetate buffer system and temperature of the reaction system played an important role in conversion of 3 to 4 . The synthesized compounds were evaluated for their in vitro anticancer activities against the strain of human breast cancer cell line MCF‐7. Compounds 3 e, 3 p, 4 h and 4 k with GI 50 below 80 μM were found to be moderately cytotoxic against MCF‐7.