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العنوان
Synthesis of some novel Pyran and Pyridine derivatives and their
use as inhibitor for the corrosion of steel in aqueous media,
antimicrobial and anticancer /
المؤلف
Anwer, Kurls Ekram.
هيئة الاعداد
باحث / Kurls Ekram Anwer
مشرف / Galal Hosni Sayed
مشرف / Hamdy Hassanian Hassan
مناقش / Nabel Abdel Moneem Negm
تاريخ النشر
2019.
عدد الصفحات
528 P. :
اللغة
الإنجليزية
الدرجة
الدكتوراه
التخصص
Organic Chemistry
تاريخ الإجازة
1/1/2019
مكان الإجازة
جامعة عين شمس - كلية العلوم - قسم الكيمياء
الفهرس
Only 14 pages are availabe for public view

from 528

from 528

Abstract

Title of thesis: Synthesis of some novel Pyran and Pyridine derivatives and their use as inhibitor for the corrosion of steel in aqueous media, antimicrobial and anticancer.
1st part: 2-amino-4H-pyran-3-carbonitrile derivative 1 was synthesized by both conventional and microwave methods. Under both microwave and conventional conditions, compound 1 was treated with chloroacetyl chloride, phenyl isocyanate, cyanoacetic acid, benzoyl chloride, T.E.O.F, acetic anhydride/H2SO4, arylidene malononitrile, urea and/or p-aminosulphaguanidine producing pyran derivatives 2-10, respectively. Meanwhile, compound 1 was allowed to react with ethyl bromoacetate, phenacyl bromide, phthalic anhydride, different aromatic amines and/or acetic acid/H2SO4 to produce compounds 11-16, respectively. On the other hand, when compound 1 was allowed to react with maleic anhydride and/or hydrazine hydrate, compounds 17 and 20 were obtained respectively. Reaction of 17 with malononitrile under different conditions gave compounds 18 and 19. While condensation of compound 20 with benzaldehyde gave product 21. The newly synthesized compounds was characterized by the spectroscopic tools IR, 1H-NMR, MS and elemental analysis. Some newly synthesized compounds have been screened in vitro antimicrobial activity against different strains of bacteria and fungi, and also were tested in vitro against two cancer cell lines, mammary gland breast cancer (MCF-7) and colon cancer (HCT-118).
2nd part: the newly synthesized compounds based on 2-amino-6-(2,4-dimethoxyphenyl)-4-(4-methoxyphenyl)pyridine-3-carbonitrile 22. The reactivity of pyridine derivative 22 was studied towards different reagents by its reaction with malononitrile, 2-(4-chlorobenzylidene)malononitrile, ethyl cyanoacetate, cyano acetic acid, m-nitro benzaldehyde, sodium azide, formamide, acetic anhydride and/or acetic anhydride/H2SO4 to give compounds 23-26,28, 31-34, respectively. The reaction of 26 with acetyl acetone gave the bipyridine derivative 27, while reaction of compound 28 with chloroacetyl chloride and phenacyl bromide gave the azetidinone derivatives 29 and 30. The formimidate 35 were obtained via reaction of compound 22 with triethylorthoformate, while reaction of 35 with phenylene diamine and/or acetamide gave the formimidamide and pyridopyrimidine derivatives 36 and 37 respectively. Compound 22 was also allowed to react with urea, thiourea, phthalic anhydride, succinic anhydride, benzoyl chloride, chloroacetonitrile, chloroacetyl chloride, p-toluenesulfonylchloride and ethyl bromoacetate to give compounds 38a,b - 45. Reaction of compound 22 with dichloro reagents in 1:1 ratio gave the bicyclic derivatives 46a–c, while its reaction with oxalyl chloride, dichloro and tetrachlorobenzoquinone derivatives, and/or dichloronaphthoquinone gave the imidazopyridine derivatives 47-50. Reaction of compound 50 with o-phenylenediamine in 1:2 ratio afforded the di-condenesed product 51 while, reaction of compound 1 with dichlororeagents in 1:2 ratio gave the bispyridine derivatives 52a-b. The newly synthesized compounds were characterized by IR, 1H-NMR and mass spectra. On the other hand the antimicrobial and anticancer activities of some of the newly synthesized compounds was studied and evaluated.
Keywords: 4H-Pyran, one-pot condensation, enaminonitrile, antimicrobial, anticancer, microwave, pyridine, one pot condensation, naphthyridine, pyrimidine, imidazole.