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العنوان
Synthesis and biological evaluation of some pyrazolopyrimidines and arylazothiazoles /
المؤلف
Mahmoud, Mohamed Nour Eldein.
هيئة الاعداد
باحث / محمد نور الدين محمود
.
مشرف / سيد عبد القادر احمد
.
مشرف / علي محمود خليفة الزناتي
تاريخ النشر
2018.
عدد الصفحات
142 P. :
اللغة
الإنجليزية
الدرجة
ماجستير
التخصص
Organic Chemistry
الناشر
تاريخ الإجازة
25/7/2018
مكان الإجازة
جامعة بني سويف - كلية العلوم - الكيمياء
الفهرس
Only 14 pages are availabe for public view

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Abstract

This work discuss synthesis and utilization of sodium salt in synthesis of some new pyrazolopyrimidines ’ aminopyridone ’ thienopyridine and pyrazolopyridine . all of structures were elucidated on the basis of elemental analysis . spectral data and alternative method synthesis
Treatment of acetyl derivative with ethyl formate in presence of sodium methoxide afforded sodium salt of compound 2 which react with 2-cyanoacetohydrazide to give aminopyridinone 7
Similarly salt of compound 2 which react with cyanothioacetamide to give 2-mercapto-6-(2-methyl-4,5-diphenyl-1H-pyrrol-3-yl)nicotinonitrile 8
sodium salt of compound 2 reacted with (E)-4-(p-tolyldiazenyl)-1H-pyrazole-3,5-diamine 5 and (E)-4-((2-chlorophenyl)diazenyl)-1H-pyrazole-3,5-diamine 6 to afford (E)-6-(2-methyl-4,5-diphenyl-1H-pyrrol-3-yl)-3-(p-tolyldiazenyl)-1,3a-dihydropyrazolo[1,5-a]pyrimidin-2-amine 9 and (E)-3-((2-chlorophenyl)diazenyl)-6-(2-methyl-4,5-diphenyl-1H-pyrrol-3-yl)-1,3a-dihydropyrazolo[1,5-a]pyrimidin-2-amine 10 respectively
Compound 8 dissolve in sodium ethoxide to give compound 11 which recreated with ethyl 2-chloroacetate to give ethyl 2-((3-cyano-6-(2-methyl-4,5-diphenyl-1H-pyrrol-3-yl)pyridin-2-yl)thio)acetate 12
On reacting 12 with pip / alcohol cyclysed and give ethyl 3-amino-6-(2-methyl-4,5-diphenyl-1H-pyrrol-3-yl)thieno[2,3-b]pyridine-2-carboxylate 13
sodium 3-cyano-6-(2-methyl-4,5-diphenyl-1H-pyrrol-3-yl)pyridine-2-thiolate 11
was reacted with iodomethane to give 6-(2-methyl-4,5-diphenyl-1H-pyrrol-3-yl)-2-(methylthio)nicotinonitrile 15.
On reacting 15 with hydrazine and pip / alcohol cyclized and give 6-(2-methyl-4,5-diphenyl-1H-pyrrol-3-yl)-1H-pyrazolo[3,4-b]pyridin-3-amine 16
Biological evaluation for synthesized compounds
The synthesized products were screened for their antimicrobial activities in vitro against two Gram‐positive bacterial species (Bacillus subtilis, Staphylococcus aureus), two Gram negative bacterial species (Escherichia coli, Salmonella typhimurium), two moulds (Aspergillus flavus, Syncephalastrum racemosum) and two yeasts (Candida albicans, Creptococcus neoformans) .
Pyrazolopyrimidine 9 – 10 and aminopyridine 7 exhibit high inhibitory effects against Aspergillus flavus
All synthesized compounds has no inhibitory effect towards Candida albicans
Pyrazolopyrimidine 9 – 10 and pyrazolopridine 16 have moderate effect against Cryptococcus neoformas
Thienopyridine 13 and pyrazolopridine 16 exhibit high inhibitory effects against Syncephalastrum racemosum
While Pyrazolopyrimidine 9 have moderate effect against Syncephalastrum racemosum
thienopyridine 13 has no inhibitory effect towards Staphylococcus aureus while Pyrazolopyrimidine 9 – 10 and pyrazolopridine 16 and aminopyridine 7 have moderate effect against Staphylococcus aureus
Pyrazolopyrimidine 9 – 10 and pyrazolopridine 16 and aminopyridine 7 have moderate effect against Bacillus subtilis
Pyrazolopyrimidine 9 – 10 exhibit high inhibitory effects against Salmonella typhimurium while aminopyridine 7 and pyrazolopridine 16 have moderate effect against Salmonella typhimurium
Pyrazolopyrimidine 9 – 10 and aminopyridine 7 have moderate effect against Escherichia coli while thienopyridine 13 has no inhibitory effect towards Escherichia coli.