title: Synthesis of some heterofunctionalized penicillanic acid derivatives and investigation of their biological activities.
abstract: 6-Substituted amino-penicillanic acid esters were synthesized starting with 6-apa. The compounds containing a 1,3-thiazole- or 1,3-thiazolidinone nucleus linked to the penicillanic acid skeleton via a hydrazino linkage were obtained from 6-apa. The treatment of carbonylamino and carbonothioylamino compounds with 4-chlorophenacyl bromide or ethyl bromoacetate gave 6-bis{4-[1,3-thiazol(idinone)amino]benzoyl}amino derivatives of 6-apa. Benzyl derivatives were synthesized in several steps, starting with 4-aminobenzoyl chloride. The treatment of 4-{[3-benzyl-4-oxo-1,3-thia(oxa)zolidin-2-ylidene]amino}benzoyl chlorides with 6-apa in ethanolic solution produced the 6-[bis(4-{[3-benzyl-4-oxo-1,3-thiazolidin-2-ylidene]amino}benzoyl)amino] derivative of penicillanic acid, while the reaction of the same intermediates in DMF gave the mono-substituted amino derivative of 6-apa. The synthesized compounds were screened for their biological activities, and some of them were found to possess good to moderate antimicrobial activity. Moreover, some of the compounds displayed antiurease, anti-β-lactamase, and/or antilipase activities.
authors.affiliation: Department of Chemistry, Karadeniz Technical University, Trabzon, Turkey.
authors.forename: Serpil
authors.initials: S
authors.lastname: Demirci
authors.forename: Ahmet
authors.initials: A
authors.lastname: Demirbas
authors.forename: Serdar
authors.initials: S
authors.lastname: Ulker
authors.forename: Sengul
authors.initials: S
authors.lastname: Alpay-Karaoglu
authors.forename: Neslihan
authors.initials: N
authors.lastname: Demirbas
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D008049:Lipase / Q000037:antagonists & inhibitors / Q000378:metabolism; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010397:Penicillanic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014510:Urease / Q000037:antagonists & inhibitors / Q000378:metabolism; D065093:beta-Lactamase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D000890:Anti-Infective Agents; D004791:Enzyme Inhibitors; D065093:beta-Lactamase Inhibitors; D010397:Penicillanic Acid; D008049:Lipase; D014510:Urease
keywords: 1,3-Oxa(thia)zole; 6-Amino penicillanic acid; Anti β-lactamase activity; Anti-urease activity; Antilipase activity; Antimicrobial activity