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Abstract
A general survey of the chemistry of isatoic anhydrides involving preparation and different groups of heterocyclic compounds that can be
prepared starting with isatoic anhydride is presented. In addition, a survey of different pharmacological activities of triazoloquinazolines including their activity as eNS modulators IS outlined. New synthetic routes for preparation of 3 different heterocyclic ring systems starting with isatoic anhydride derivatives are presented: I) Triazoloquinazoline: • 6-Substituted-5-(substitutedphenyl)-5,6-dihydr-l ,2,4-triazolo [4,3-c]quinazoline-3-thiol (Va. f) are prepared by refluxing the intermediate 5-(2-substituted aminophenyl)-l ,2,4-triazol-3-thiol (IVa,b) with aromatic aldehyde. • Reacting the intermediate IV with formaldehyde gave 3- hydroxymethyl-6-substituted-5,6-dihydro-l ,2,4-triazolo[ 1,5- c ]quinazolin-2-thione (VIIa,b). • Refluxing compounds V with formaldehyde caused isomerization to the triazolo[ 1 ,5-c ]quinazoline Isomer. However, the product was found to differ according to the nature of the 5-aryl substituent of compound V and the time of reflux. 2) Triazolobenzotriazepine: •Four different 1 ,2,4-triazolo[ 4,3-d]benzotriazepine-3-thiol derivatives (XVa-d) are prepared by reacting the intermediate 4- amino_5_(2_substitutedaminophenyl)-1 ,2,4-triazol-3-thio! (XIVa-c) with different orthoesters. • Reacting XVIa with orthoacetate gave fused tetracyclic compound instead of 6-methyl-5H-l ,2,4-triazol[ 4,3-d11,3 ,4- benzotriazepine- 3 - thio L 3) Quinazolinone: • Three different N_(4_0xo_3_quinazolinyl)succinimide or phthalimide derivatives (XVIII a-c) are prepared by reacting succmlC or phthalic anhydride with 2-methylamino
benzoyl hydrazide followed by cyclization with different aldehydes. • Five other 3-( 4-substituted benzylidineamino )-1-methyl-2,3- dihydro-4[lH1-quinazolinone derivatives (XXa-e) are prepared by reacting N_(2_methylaminobenzoyl)-N’-( 4- substituted benzylidine )hydrazine (XIXa-d) with different aldehydes- Finally, all the newly synthesized final compounds were subjected to pharmacological testing for their CNS effect as stimulants or depressants applying preliminary screening in mice and EEG recording in rabbits, the following compounds showed activity: • Compound VIla which belongs to the triazo!oquinazoline series was found to have CNS stimulating activity. • Comound XVId which belongs to the triazolobenzotriazepine series was found to have CNS depressant action.