title: Synthesis and preliminary ex vivo evaluation of the spasmolytic activity of 1,3-thiazolium- and 1,3,4-thiadiazolium-5-methylthio- and 5-thioacetate derivatives.
abstract: Seven new compounds have been synthetized in satisfactory yields (51-78 %) through the treatment of mesoionic 1,3-thiazolium-5-thiolate (4a-d) and 1,3,4-thiadiazolium- 5-thiolate (10a,b) with chloroacetic acid or methyl iodide: 1,3,4-thiadiazolium-5-methylthio- (11) and 5-thioacetate (12). The structure of the title compounds was elucidated by elemental analysis, IR, (1)H and (13)C NMR spectroscopy. The newly synthesized compounds 5a, 6a, 11 and 12 were evaluated for their ex vivo spasmolytic potential on four isolated smooth muscles (rat aorta and uterus, guinea pig ileum and trachea) and compared with scopolamine. Some of the compounds exhibited potent spasmolytic activity equal to or stronger than scopolamine.
authors.forename: José A S
authors.initials: JA
authors.lastname: Luis
authors.forename: Thiago M De
authors.initials: TM
authors.lastname: Aquino
authors.forename: Bruno F
authors.initials: BF
authors.lastname: Lira
authors.forename: Petrônio F A
authors.initials: PF
authors.lastname: Filho
authors.forename: Marcus T
authors.initials: MT
authors.lastname: Scotti
authors.forename: Luciana
authors.initials: L
authors.lastname: Scotti
authors.forename: Ricardo O De
authors.initials: RO
authors.lastname: Moura
authors.forename: Francisco J B Mendonça
authors.initials: FJ
authors.lastname: Junior
mesh_terms: D000818:Animals; D001011:Aorta / Q000187:drug effects; D005260:Female; D006168:Guinea Pigs; D007082:Ileum / Q000187:drug effects; D008297:Male; D009130:Muscle, Smooth / Q000187:drug effects; D010276:Parasympatholytics / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D051381:Rats; D017208:Rats, Wistar; D012601:Scopolamine / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014132:Trachea / Q000187:drug effects; D014599:Uterus / Q000187:drug effects
chemical_list: D010276:Parasympatholytics; D012601:Scopolamine