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Synthesis and Anticancer and Antiviral Activities of New 2‐Pyrazoline‐Substituted 4‐Thiazolidinones
Author(s) -
Havrylyuk Dmytro,
Zimenkovsky Borys,
Vasylenko Olexandr,
Lesyk Roman
Publication year - 2013
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1056
Subject(s) - chemistry , acetamide , pyrazoline , in vitro , aryl , maleic anhydride , selectivity , stereochemistry , combinatorial chemistry , medicinal chemistry , biochemistry , organic chemistry , alkyl , copolymer , catalysis , polymer
2‐(4,5‐Dihydropyrazol‐1‐yl)‐thiazol‐4‐ones ( 2–5 ) have been synthesized starting from 3‐phenyl‐5‐aryl‐1‐thiocarbamoyl‐2‐pyrazolines via [2+3]‐cyclization with 2‐bromopropionic acid, maleic anhydride, N ‐arylmaleimides, and aroylacrylic acids. The in vitro anticancer activity of 2a , 3a , 4a , 5b , and 5c were tested by the National Cancer Institute. Compounds 4a , 5b , and 5c demonstrated selective inhibition of leukemia cell lines growth at a single concentration (10 −5 M). The screening of antiviral activity for a broad panel of viruses revealed that N ‐(4‐methoxyphenyl)‐2‐{2‐[5‐(4‐methoxyphenyl)‐3‐phenyl‐4,5‐dihydropyrazol‐1‐yl]‐4‐oxo‐4,5‐dihydrothiazol‐5‐yl}‐acetamide 4a was highly active against Tacaribe TRVL 11 573 virus strain (EC 50 = 0.71 μg/mL, selectivity index = 130).

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