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Acta Pharmaceutica, Vol. 64 No. 2, 2014.

Original scientific paper

https://doi.org/10.2478/acph-2014-0016

Synthesis and preliminary ex vivo evaluation of the spasmolytic activity of 1,3-thiazolium- and 1,3,4-thiadiazolium-5-methylthio- and 5-tioacetate derivatives

JOSÉ A. S. LUIS orcid id orcid.org/0000-0003-3588-833X ; Centro de Educação e Saúde, Universidade Federal de Campina Grande, 58175-000, Cuité-PB, Brazil
THIAGO M. DE AQUINO ; Instituto de Química e Biotecnologia, Universidade Federal de Alagoas, 57072-970, Maceió-AL, Brazil
BRUNO F. LIRA ; Departamento de Química, Universidade Federal da Paraíba, 58051-900, João Pessoa-PB, Brazil
PETRÔNIO F. A. FILHO ; Departamento de Química, Universidade Federal da Paraíba, 58051-900, João Pessoa-PB, Brazil
MARCUS T. SCOTTI ; Departamento de Engenharia e Meio Ambiente, Universidade Federal da Paraíba, Campus IV, 58297-000, Rio Tinto-PB, Brazil
LUCIANA SCOTTI ; Departamento de Ciências Biológicas, Universidade Estadual da Paraíba, CCBSA, João Pessoa-PB 58070-450, Brazil
FRANCISCO J. B. MENDONÇA JUNIOR ; Departamento de Ciências Biológicas, Universidade Estadual da Paraíba, CCBSA, João Pessoa-PB 58070-450, Brazil

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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-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

Hrčak ID:

114600

URI

https://hrcak.srce.hr/114600

Publication date:

30.6.2014.

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