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Synthesis of 5-arylidene-2-amino-4-azolones and evaluation of their anticancer activity.

Abstract：

:Series of novel 5-arylidene-2-arylaminothiazol-4(5H)-ones and 2-aryl(benzyl)amino-1H-imidazol-4(5H)-ones were synthesized from appropriate 2-alkylthioazol-4-ones using nucleophilic substitution in position 2 by various anilines and benzylamines and Knoevenagel reaction. X-ray structural studies of 22 revealed the structure to be intermediate between amino and imino tautomeric forms. All the target compounds were evaluated for the anticancer activity in vitro in standard National Cancer Institute 60 cancer cell lines assay. Majority of compounds showed significant antitumor cytotoxicity effect at micromolar and submicromolar level (Mean LogGI50 ranges -5.77 to -4.35). Some of the most potent compounds, namely 10 and 13, possessed selectively high effect on all leukemia cell lines at submicromolar level (Mean LogGI50 [leukemia lines], respectively, -6.41 and -6.29), which are probably associated with immunosuppressive activity. Individual cancer cell lines sensitivity to synthesized compounds and SAR studies are discussed. COMPARE analysis allowed to disclose probable modes of anticancer action for synthesized compounds, in particular showed number of high correlations with activity patterns of alkylating agents (PCC approximately 0.606-0.731).

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Subtel'na I,Atamanyuk D,Szymańska E,Kieć-Kononowicz K,Zimenkovsky B,Vasylenko O,Gzella A,Lesyk R

doi

10.1016/j.bmc.2010.05.073

subject

Has Abstract

pub_date

2010-07-15 00:00:00

pages

5090-102

issue

14

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(10)00504-3

journal_volume

18

pub_type

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