title: Microwave assisted synthesis of some hybrid molecules derived from norfloxacin and investigation of their biological activities.
abstract: Norfloxacin was converted to 7-(4-amino-2-fluorophenyl)piperazin derivative (2) via the formation of nitro compound. The synthesis of the norfloxacin derivatives containing 1,3-thiazole or 1,3-thiazolidin moiety was performed from the reaction of 4-chlorophenacylbromide or ethyl bromoacetate with compounds 4-7 obtained starting from 2. 3-Fluoro-4-[4-(2-methoxyphenyl)piperazin-1-yl]aniline (14), 5-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-4-phenyl-4H-1,2,4-triazole-3-thiol (18) and {[4-(2-methoxy phenyl)piperazin-1-yl]methyl}-1,3,4-oxadiazol-2-thiol (19) were obtained starting from 1-(2-methoxyphenyl)piperazine by several steps. The treatment of hydrazide (16) with several aldehydes afforded N'-[(2-hydroxyphenyl)methylen]- (20), N'-[(3-hydroxy-4-methoxy phenyl)methylen]- (21) or N'-[1H-indol-3-ylmethylene]-2-[4-(2-methoxyphenyl)piperazin-1-yl]acetohydrazide (22). Then, compounds 14, 18, 19 and 22 were condensed with 7-[4-(chloroacetyl)piperazin-1-yl]-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (3) that was obtained from norfloxacine. All newly synthesized compounds were screened for their antimicrobial activities and some of them exhibited excellent activity. Moreover, one compound was found to have antiurease activity.
authors.affiliation: Karadeniz Technical University, Department of Chemistry, 61080 Trabzon, Turkey.
authors.forename: Meltem Yolal
authors.initials: MY
authors.lastname: Mentese
authors.forename: Hacer
authors.initials: H
authors.lastname: Bayrak
authors.forename: Yıldız
authors.initials: Y
authors.lastname: Uygun
authors.forename: Arif
authors.initials: A
authors.lastname: Mermer
authors.forename: Serdar
authors.initials: S
authors.lastname: Ulker
authors.forename: Sengul Alpay
authors.initials: SA
authors.lastname: Karaoglu
authors.forename: Neslihan
authors.initials: N
authors.lastname: Demirbas
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008872:Microwaves; D015394:Molecular Structure; D009643:Norfloxacin / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014510:Urease / Q000037:antagonists & inhibitors / Q000378:metabolism
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D004791:Enzyme Inhibitors; D014510:Urease; D009643:Norfloxacin
keywords: 1,2,4-Triazole; 1,3-Thiazole; Antimicrobial activity; Antiurease activity; Norfloxacin