Acta Pharm. 64 (2014) 233-245

 

full paper

Original research paper

 

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

JOSÉ A. S. LUIS, THIAGO M. DE AQUINO, BRUNO F. LIRA, PETRÔNIO F. A. FILHO, MARCUS T. SCOTTI, LUCIANA SCOTTI, RICARDO O. DE MOURA and FRANCISCO J. B. MENDONÇA JUNIOR

franciscojbmendonca@yahoo.com.br; joseasl@ufcg.edu.br

1 Centro de Educação e Saúde, Universidade Federal de Campina Grande, 58175-000, Cuité-PB, Brazil

2 Instituto de Química e Biotecnologia, Universidade Federal de Alagoas, 57072-970, Maceió-AL, Brazil

3 Departamento de Química, Universidade Federal da Paraíba, 58051-900, João Pessoa-PB, Brazil

4 Departamento de Engenharia e Meio Ambiente, Universidade Federal da Paraíba, Campus IV, 58297-000, Rio Tinto-PB, Brazil

5 Departamento de Ciências Biológicas, Universidade Estadual da Paraíba, CCBSA, João Pessoa-PB 58070-450, Brazil

Accepted January 21, 2014

 

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-thiazolium-5-methylthio- (5a-c), 5-thioacetate (6a,b) and 1,3,4-thiadiazolium-5-methylthio- (11) and 5-thioacetate (12). The structure of the title compounds was elucidated by elemental analysis, IR, 1H and 13C 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.

 

Keywords: 1,3-thiazolium, 1,3,4-thiadiazolium, mesoionic derivatives, spasmolytic activity