Synthesis and Anticancer Activity of Isatin-Based Pyrazolines and Thiazolidines Conjugates

✍ Scribed by Dmytro Havrylyuk; Natalya Kovach; Borys Zimenkovsky; Olexandr Vasylenko; Roman Lesyk

• Book ID: 101641653
• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 148 KB
• Volume: 344
• Category: Article
• ISSN: 0365-6233
• DOI: 10.1002/ardp.201100055

✦ Synopsis

Abstract

The synthesis and antitumor activity screening of novel isatin based conjugates with thiazolidine and pyrazoline moieties were performed. Reaction of 3,5‐diaryl‐4,5‐dihydropyrazoles with chloroacetyl chloride yielded starting 2‐chloro‐1‐(3,5‐diaryl‐4,5‐dihydropyrazol‐1‐yl)‐ethanones which were utilized in alkylation of isatin and 5‐bromoisatin. Thus, corresponding 1‐[2‐(3,5‐diaryl‐4,5‐dihydropyrazol‐1‐yl)‐2‐oxoethyl]‐1__H__‐indole‐2,3‐diones (1a–1d) have been obtained. The compounds 1a–1d have been used in Knoevenagel condensation with 4‐thiazolidinones for obtaining a series of 5‐ylidenederivatives 2a–2f and 3a–3d. The synthesized compounds were tested for their anticancer activity in NCI60 cell lines. Among the tested compounds, 5‐bromo‐1‐{2‐[5‐(4‐chlorophenyl)‐3‐(4‐methoxyphenyl)‐4,5‐dihydropyrazol‐1‐yl]‐2‐oxoethyl}‐1__H__‐indole‐2,3‐dione (1d) was found to be the most active candidate with selective influence on leukemia subpanel tumor cell lines with GI~50~ values range of 0.69–3.35 µM.