title: Synthesis and antimicrobial activity of some new heterocycles incorporating the pyrazolopyridine moiety.
abstract: 2-Cyano-N-(4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)acetamide (2) was utilized as key intermediate for the synthesis of some new coumarin 3, pyridine 4, pyrrole 5, thiazole 8, pyrido[2',3':3,4]-pyrazolo-[5,1-c]triazine 7, and aminopyrazolo 10 compounds. 2-Cyano-N-(4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-3-(dimethylamino)acrylamide (11) was synthesized and allowed to react with hydroxylamine, hydrazine, and guanidine to afford regioselectively the isoxazole 13, pyrazole 15, and pyrimidine 17 derivatives, respectively. The reaction of 11 with thiourea and/or with ethyl glycinate in basic medium afforded the regioisomeric pyrimidinethione 18 and 3,5-dioxo-1,4-diazepine-6-carbonitrile 23. All the synthesized products were tested and evaluated as antimicrobial agents.
authors.affiliation: Faculty of Science of Girls, King Khaled University, Abha, Saudi Arabia.
authors.forename: Sraa
authors.initials: S
authors.lastname: Abu-Melha
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001412:Bacillus subtilis / Q000187:drug effects / Q000254:growth & development; D001413:Bacillus thuringiensis / Q000187:drug effects / Q000254:growth & development; D020171:Botrytis / Q000187:drug effects / Q000254:growth & development; D004926:Escherichia coli / Q000187:drug effects / Q000254:growth & development; D005670:Fusarium / Q000187:drug effects / Q000254:growth & development; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011550:Pseudomonas aeruginosa / Q000187:drug effects / Q000254:growth & development; D011720:Pyrazoles / Q000494:pharmacology*; D011725:Pyridines / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D000935:Antifungal Agents; D011720:Pyrazoles; D011725:Pyridines; C118531:pyrazolopyridine
keywords: Aminopyrazole; Antimicrobial activity; Pyrazolo[3,4-b]pyridine; Pyridine; Pyrimidine