Synthesis of Novel 6,7,8,9-Tetrahydro-5H-5-hydroxyphenyl-2-benzylidine- 3-substituted Hydrazino Thiazolo (2,3-b) Quinazoline as Potent Antinociceptive and Anti-inflammatory Agents

摘要

A series of 6,7,8,9-tetrahydro-5H-5-hydroxyphenyl-2-benzylidine-3-substituted hydrazino thiazolo (2,3-b) quinazolines have been synthesized to meet the structural requirements essential for anti-inflammatory and antinociceptive properties. The synthesized series of heterocycles, 6,7,8,9-tetrahydro-5H-5-hydroxyphenyl-2-benzylidine-3-substituted hydrazino thiazolo (2,3-b) quinazoline by the reaction of 6,7,8,9-tetrahydro-5H-5-hydroxy phenyl thiazolo (2,3-b) quinazolin-3(2H)-one with appropriate hydrazine hydrate and ketones/aldehydes in the presence of anhydrous sodium acetate and glacial acetic acid as presented in Scheme 1. Their antinociceptive activity were evaluated by tailflick technique, anti-inflammatory was evaluated by carrageenan-induced paw edema test and their ulcerogenicity index determined by reported protocol. The compounds exhibited the lowest ulcer index (0.51 【 1.63, 0.48 【 1.28 and 0.50 【 1.53, respectively. The 6,7,8,9-tetrahydro-5H-5-hydroxy phenylhydroxy-2-benzylidine-3-(N`-3-pentylidenehydrazino) thiazolo (2,3-b) quinazoline and 6,7,8,9-tetrahydro-5H-5-hydroxy phenyl-2-benzylidine-3-(N`-2-pentylidene- hydrazino) thiazolo (2,3-b) quinazoline exhibited the most potent antinociceptive and anti-inflammatory activities.