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Synthesis and Anticancer and Antiviral Activities of New 2-Pyrazoline-Substituted 4-Thiazolidinones

Authors :
Borys Zimenkovsky
Roman Lesyk
Dmytro Havrylyuk
Olexandr Vasylenko
Source :
Journal of Heterocyclic Chemistry. 50:E55-E62
Publication Year :
2013
Publisher :
Wiley, 2013.

Abstract

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 (EC50 = 0.71 μg/mL, selectivity index = 130).

Details

ISSN :
0022152X
Volume :
50
Database :
OpenAIRE
Journal :
Journal of Heterocyclic Chemistry
Accession number :
edsair.doi...........ff66d803980084aa077d8edf1f5e6e31
Full Text :
https://doi.org/10.1002/jhet.1056