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العنوان
Synthesis and biological properties of new multi functionalized organic compounds based on cyclic ketones /
المؤلف
Said, Gehad Ebrahim El-Sayed El-Sayed.
هيئة الاعداد
باحث / جهاد ابراهيم السيد السيد سعيد
مشرف / مرجريت منصور جرجس
مشرف / ابراهيم عبدالجليل عبدالسلام
مناقش / محمد حسن عبد الرحمن شريف
مناقش / تامر كمال امين
الموضوع
biological. cyclic ketones.
تاريخ النشر
2022.
عدد الصفحات
online resource (251 pages) :
اللغة
الإنجليزية
الدرجة
الدكتوراه
التخصص
الكيمياء
تاريخ الإجازة
1/1/2022
مكان الإجازة
جامعة المنصورة - كلية العلوم - قسم الكيمياء
الفهرس
Only 14 pages are availabe for public view

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Abstract

Part I: Synthesis of new multifunctional cyclohexenone derivatives The cyclohexenone 1 was reacted with different hydrazides to prepare a series of new compounds 2-8.Thiazoles 9-12 were prepared by heterocyclization of 6 with different α-halocarbonyl derivatives and hydrazonyl halides. Arylidenes 13 (a-c) were obtained by Knoevenagel reaction of 7 with different aldehydes. On the other hand, the cyclocondensation of 7 with salicylicaldehyde and 2-hydroxy-1-naphthaldehyde produced 14 and 15, respectively. Treatment of compounds 7 and 13a with hydrazine resulted in pyrazole derivatives 16 and 17, respectively. Also, the reaction of cyanoacetylhydrazone derivative 7 towards coupling with diazonium salts formed from compound 8 and p-toluidine was studied to provide the proposed hydrazo derivatives 18a and 18b. The triethylamine promoted Gewald reaction of 7 with phenyl isothiocyanate in ethanol containing elemental sulphur led to the formation of aminothiazole product 19, while reaction with acetylacetone gave a dimethylpyridone derivative 20. Compound 8 was used to obtain cyanoacetamide derivative 21, which in turn reacted with different aldehydes to obtain arilidines 22a and 22b. The cyclocondensation of 21 with salicyldehyde and 2-hydroxy-1-naphthaldehyde produced compounds 23 and 24. The arilidene malononitrile 25 was prepared from compound 1 with malononitrile. The trial to synthesize the amino pyrazole derivative 26’ by refluxing an ethanolic solution of compound 25 with hydrazine hydrate failed and gave instead the bis-(arylidene) hydrazine 26. The azo coupling of compound 1 with aniline and p-toluidine was performed in the presence of NaOH (40%) to give the corresponding arylazo products 27a and 27b, respectively. The hydrazone derivative 28 was synthesized which in turn reacted with a series of different aldehydes and ketones to produce unsymmetrical and symmetrical azines 29-36. The diazonium salt 37 was formed from hydrazone 28. Coupling of 37 with resorcinol, morpholine and malononitrile gave triazines 38-40. Aminopyrazole 41 is derived by reaction with hydrazine. Coupling of aryl diazonium chloride of aniline, 4-nitroaniline or 4-aminohypuric acid with 28 produced tetrazines 42 (a-c). A similar coupling of 28 with the diazonium salt of the compound p-phenylenediamine gave 43. The reaction of 42c with 4-formylphenylbenzoate according to the well-known Erlenmeyer method afforded oxazolone 44.Part 2: Biological activity2.1. Antioxidant activityThe antioxidant activity of all new compounds (2-44) was determined. Compounds 11a and 39 showed the highest inhibition values.2.2. Antimicrobial activity The antimicrobial activities of newly synthesized compounds 2-44 were evaluated against S. aureus, E. Coli and C. albicans and most of compounds showed good inhibition as antimicrobial agents.2.3. Cytotoxicity activityThe most active compounds were evaluated in vitro for their cytotoxic activities against normal human fetal lung fibroblast (WI-38) cell line and Doxorubicin as a standard anticancer drug for comparison.