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العنوان
The Utility of isatoic anhydrides in the synthesis of New Heterocyclic Compounds for Biological Study /
المؤلف
Ziedan, Noha Ibrahim EL-Sayed.
هيئة الاعداد
باحث / نهى إبراهيم السيد زيدان
مشرف / / عبد الله أحمد الشنوانى
مشرف / صبحى محمد العدل
مشرف / سامى مجاهد إبراهيم
الموضوع
Anhydrides.
تاريخ النشر
2004 .
عدد الصفحات
183 P. :
اللغة
الإنجليزية
الدرجة
ماجستير
التخصص
الصيدلة ، علم السموم والصيدلانيات (المتنوعة)
تاريخ الإجازة
1/1/2004
مكان الإجازة
جامعة الزقازيق - كــليـــة الصيدلــــة - Pharmaceutical Chemistry
الفهرس
Only 14 pages are availabe for public view

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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 CNS modulators is outlined.New synthetic routes for preparation of 3 different heterocyclic ring systems starting with isatoic anhydride derivatives are presented:
1) Triazoloquinazoline: 6-Substituted-5-(substitutedphenyl)-5,6-dihydr-1,2,4-triazolo [4,3-c]quinazoline-3-thiol (Va-f) are prepared by refluxing the intermediate 5-(2-substituted aminophenyl)-1,2,4-triazol-3-thiol (IVa,b) with aromatic aldehyde. Reacting the intermediate IV with formaldehyde gave 3-hydroxymethyl-6-substituted-5,6-dihydro-1,2,4-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-thiol (XIVa-c) with different orthoesters. Reacting XVIa with orthoacetate gave fused tetracyclic compound instead of 6-methyl-5H-1,2,4-triazol[4,3-d]1,3,4-benzotriazepine-3-thiol. Quinazolinone: Three different N-(4-oxo-3-quinazolinyl)succinimide or phthalimide derivatives (XVIIIa-c) are prepared by reacting succinic or phthalic anhydride with 2-methylamino benzoylhydrazide followed by cyclization with different aldehydes. Five other 3-(4-substituted benzylidineamino)-1-methyl-2,3-dihydro-4[1H]-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: