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Acta Pharmaceutica, Vol.66 No.3 September 2016. -

6-4-Chlorophenyl-spirocyclohexane-1,2-thieno3,2-d1,3oxazin-41H-one 1 was synthesized and used as a starting material for the synthesis of a novel series of spiro compounds having biologically active sulfonamide 2a-e and 3-4-acetylphenyl-6-4-chlorophenyl-1H-spirocyclohexane-1,2-thieno3,2-dpyrimidine-43H-one 3. Compound 2a was used as a key intermediate for the synthesis of sulfonyl carbothioamide derivatives 4a-c. Also, compound 3 was used as an intermediate for the synthesis of 3H-spirocyclohexane-1,2-thieno3,2-dpyrimidin-3-ylphenyl}-2-imino-4-substituted phenyl and-or thienyl-1,2-dihydropyridine-3-carbonitrile derivatives 5a-e, 3H-spirocyclohexane-1,2-thieno3,2-dpyrimidin-3-ylphenyl}-2-oxo-4-substituted phenyl and-or thienyl-1,2-dihydropyridine-3-carbonitrile derivatives 6a-e, and 4-2Z-3-substituted-arylprop-2-enoylphenyl-1H-spirocyclohexane-1,2-thieno3,2-dpyrimidine derivatives 7a-e. Cyclocondensation of 7a-e with hydrazine hydrate produced 6-4-chlorophenyl-3-4-5-substituted aryl-4,5-dihydro-1H-pyrazol-3-ylphenyl-1H-spirocyclohexane-1,2-thieno-3,2-dpyrimidin-43H-ones 8a-e, but with hydroxylamine hydrochloride afforded the corresponding isoxazoline derivatives 9a-e. Also, cyclocondensation by thiourea afforded 2-thioxo-1,2-dihydropyrimidin-4-yl-phenyl-spiro-{cyclohexanethieno3,2-dpyrimidin}-4-one derivatives 10a-e. The new compounds were investigated for antimicrobial activity. Compounds 2c, 8b, c, 9b and 10b were the most potent ones against both Gram-negative and Gram-positive bacteria. Compound 8c exhibited higher antifungal activity towards the examined fungi with MIC of 1–2 µmol mL–1 compared to ketoconazole MIC 2–3 µmol mL–1.

thieno3,2-d1,3oxazin-4-one; thieno3,2-dpyrimidines; N-nucleophiles; spiro-thieno3,2-dpyrimidine; ring transformation; antimicrobial



Autor: HEND N. HAFEZ - orcid.org-0000-0003-1541-8744 ; Al-Imam Mohammad Ibn Saud Islamic University IMSIU, College of Science, Departmen

Fuente: http://hrcak.srce.hr/



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