- 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.
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.
Acta pharmaceutica (Zagreb, Croatia) (2014-06-11)
José A S Luis, Thiago M De Aquino, Bruno F Lira, Petrônio F A Filho, Marcus T Scotti, Luciana Scotti, Ricardo O De Moura, Francisco J B Mendonça Junior
PMID24914723
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.
MATERIALS
Product Number
Brand
Product Description
Carbachol, European Pharmacopoeia (EP) Reference Standard
Sigma-Aldrich
Aluminum oxide, nanopowder, 13 nm primary particle size (TEM), 99.8% trace metals basis
Sigma-Aldrich
Aluminum oxide, nanoparticles, <50 nm particle size (DLS), 20 wt. % in isopropanol
Sigma-Aldrich
Aluminum oxide, powder, primarily α phase, ≤10 μm avg. part. size, 99.5% trace metals basis