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Substituted Quinazolines, Part 2. Synthesis and In-Vitro Anticancer Evaluation of New 2-Substituted Mercapto-3H-quinazoline Analogs

✍ Scribed by Ashraf A. Khalil; Sami G. Abdel Hamide; Abdulrahman M. Al-Obaid; Hussein I. El-Subbagh

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
170 KB
Volume
336
Category
Article
ISSN
0365-6233

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✦ Synopsis

Abstract

A new series of 2‐substituted mercapto‐3__H__‐quinozolines bearing 6‐iodo and 2‐heteroarylthio functions was synthesized and screened for their in vitro antitumor activity. Eighteen compounds were identified as active anticancer agents. N′‐[(3‐Benzyl‐4‐oxo‐6‐iodo‐3__H__‐quinazoline‐2‐yl)thioacetyl]‐N^3^‐ethylthiosemicarbazide (10), N‐benzoyl‐N′‐[2‐(3‐benzyl‐4‐oxo‐6‐iodo‐3__H__‐quinozolin‐2‐yl)thioacetyl]hydrazine (12), and 2‐[(3, 6‐dioxo‐pyridazin‐4‐yl)thio]‐3‐benzyl‐4‐oxo‐6‐iodo‐3__H__‐quinazoline (20) proved to be the most active members in this study. They showed MG‐MID, GI~50~ values of 12.8, 11.3, and 13.8 μM, respectively. The detailed synthesis and biological screening data are reported.

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A variety of 3-(4-methyl phenyl)-2-substituted amino-3H-quinazolin-4-ones were synthesized by reacting the amino group of 2-hydrazino-3-(4-methyl phenyl)-3H-quinazolin-4-one with a variety of aldehydes and ketones. The starting material 2-hydrazino-3-(4-methyl phenyl)-3H-quinazolin-4one was synthesi