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العنوان
biological activity and mass spectral fragmentation patterns of some prepared nitrogen heterocycles \
المؤلف
mossalam, ahmed mohamed mohamed.
هيئة الاعداد
باحث / أحمد محمد محمد مسلم
مشرف / إبراهيم السيد محي الدين
مشرف / الشربيني حمدي السيد يوسف
مشرف / محمد عبد المنعم محمود
مناقش / عاطف محمد عبد الحميد عامر
مناقش / جيهان عبد الرازق حسنين
الموضوع
biological activity. mass spectral fragmentation patterns. prepared nitrogen heterocycles.
تاريخ النشر
2014.
عدد الصفحات
124, 7 leaves :
اللغة
الإنجليزية
الدرجة
ماجستير
التخصص
الكيمياء
تاريخ الإجازة
1/1/2014
مكان الإجازة
جامعة بورسعيد - كلية العلوم ببورسعيد - الكيمياء
الفهرس
Only 14 pages are availabe for public view

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Abstract

SUMMARY
It is well known that coumarin derivatives possess different pharmacological activities especially their applications as anti-inflammatory, anti-allergic, hepatoprotective, spazmolitic, antiviral, anti-carcinogenic and anti-coagulant activities. The present thesis deals with the behavior of some coumarin derivatives in reactions with some nucleophiles (namely, hydrazine hydrate, ethylenediamine , and thiosemicarbazide).
The starting materials 3-acetylbenzocoumarin 2a and 3-ethoxycarbonyl benzocoumarin 2b were prepared from reaction between a mixture of 2-hydroxy-1-naphthaldehyde 1 and active methylene (such as ethylacetoacetate and diethylmalonate, respectively) in presence of piperedine.
The reaction of a mixture of 2a and /or 2b and ethylenediamine in the presence of ethanol afforded the product 1,2-Bis[(o-hydroxy-1-naphthaldiene)amino]ethane 5. The expected 1,4-diazepene cyclocondensation products 3 or 4 were not achieved.
Compounds 2(a,b) react with hydrazine hydrate in ethanol and leads to the formation of 2-hydroxy-1-naphthaldazine 8. The synthesis of cyclocondensation product imidazolobenzocoumarin 6 and/or 7 was failed.
Acetylation of 2-hydroxy-1-naphthaldazine 8 by using acetic anhydride was carried out affording 2-Acetoxy-1-naphthaldazine 9.
Condensation of 2b with thiosemicarbazide in the presence of anhydrous potassium carbonate leads to the formation of 2-hydroxyl-1-naphthaldehydethiosemicarbazone 12.
Acetylation of 2- hydroxyl-1-naphthaldehyde thiosemicarbazone 12 by refluxing with acetic anhydride yielded the product 4-(2-acetroxy naphthaldiene-1-yl)-1,3-diacetylthiosemicarbazide 13.
Treatment of N-benzoylglycine 14 with 5-bromo-2-hydroxyaldehyde and 2-hydroxyl-1-naphthaldehyde in the presence of acetic anhydride and fused sodium acetate gives 6-bromo-3-benzoylaminocoumarin 15 and 3-benzoylaminobenzocoumarin 16 respectively.
Also the treatment of 6-bromo-3-benzoylaminocoumarin 15 and 3-benzoylaminobenzocoumarin 16 with hydrazine hydrate gives 6-bromo-salicyladazine 18 and 2-hydroxyl-1-naphthaldazine 8 respectively.
The purity of the synthesized compounds was checked by TLC and the structures of synthesized compounds were confirmed from elemental analysis, 1H-NMR , 13C-NMR and Mass spectroscopy. The mass spectral fragmentation patterns of some prepared compounds were investigated to elucidate the structure of the synthesized compounds.
The synthesized compounds were screened for their antioxidant and anticancer activities. The results of the provided samples shows different activities. It was found that compounds 8, 13 and 18 were active against antioxidant. Compounds 13 and 18 were also highly active against MCF-7 and HEPG-2 cell lines.