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

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 struc...

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Main Authors: Luis José A. S., Aquino Thiago M. De, Lira Bruno F., Filho Petrônio F. A., Scotti Marcus T., Scotti Luciana, Moura Ricardo O. De, Junior Francisco J. B. Mendonça
Format: Article
Language:English
Published: Sciendo 2014-06-01
Series:Acta Pharmaceutica
Subjects:
1,3-thiazolium
1,3,4-thiadiazolium
mesoionic derivatives
spasmolytic activity
Online Access:http://www.degruyter.com/view/j/acph.2014.64.issue-2/acph-2014-0016/acph-2014-0016.xml?format=INT
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spelling doaj-746872d23d5148b8bb3e31e66452de1f2020-11-25T02:00:59ZengSciendoActa Pharmaceutica1330-00751846-95582014-06-0164223324510.2478/acph-2014-0016acph-2014-0016Synthesis and preliminary ex vivo evaluation of the spasmolytic activity of 1,3-thiazolium- and 1,3,4-thiadiazolium-5-methylthio- and 5-thioacetate derivativesLuis José A. S.0Aquino Thiago M. De1Lira Bruno F.2Filho Petrônio F. A.3Scotti Marcus T.4Scotti Luciana5Moura Ricardo O. De6Junior Francisco J. B. Mendonça7Centro de Educação e Saúde Universidade Federal de Campina Grande 58175-000, Cuité-PB, BrazilInstituto de Química e Biotecnologia Universidade Federal de Alagoas 57072-970, Maceió-AL, BrazilDepartamento de Química, Universidade Federal da Paraíba, 58051-900 João Pessoa-PB, BrazilDepartamento de Química, Universidade Federal da Paraíba, 58051-900 João Pessoa-PB, BrazilDepartamento de Engenharia e Meio Ambiente, Universidade Federal da Paraíba Campus IV, 58297-000, Rio Tinto-PB, BrazilDepartamento de Ciências Biológicas Universidade Estadual da Paraíba CCBSA, João Pessoa-PB 58070-450 BrazilDepartamento de Ciências Biológicas Universidade Estadual da Paraíba CCBSA, João Pessoa-PB 58070-450 BrazilDepartamento de Ciências Biológicas Universidade Estadual da Paraíba CCBSA, João Pessoa-PB 58070-450 BrazilSeven 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, 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 scopolaminehttp://www.degruyter.com/view/j/acph.2014.64.issue-2/acph-2014-0016/acph-2014-0016.xml?format=INT1,3-thiazolium1,3,4-thiadiazoliummesoionic derivativesspasmolytic activity
collection DOAJ
language English
format Article
sources DOAJ
author Luis José A. S.
Aquino Thiago M. De
Lira Bruno F.
Filho Petrônio F. A.
Scotti Marcus T.
Scotti Luciana
Moura Ricardo O. De
Junior Francisco J. B. Mendonça
spellingShingle Luis José A. S.
Aquino Thiago M. De
Lira Bruno F.
Filho Petrônio F. A.
Scotti Marcus T.
Scotti Luciana
Moura Ricardo O. De
Junior Francisco J. B. Mendonça
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
1,3-thiazolium
1,3,4-thiadiazolium
mesoionic derivatives
spasmolytic activity
author_facet Luis José A. S.
Aquino Thiago M. De
Lira Bruno F.
Filho Petrônio F. A.
Scotti Marcus T.
Scotti Luciana
Moura Ricardo O. De
Junior Francisco J. B. Mendonça
author_sort Luis José A. S.
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
title_short 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_sort 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
publisher Sciendo
series Acta Pharmaceutica
issn 1330-0075
1846-9558
publishDate 2014-06-01
description 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, 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
topic 1,3-thiazolium
1,3,4-thiadiazolium
mesoionic derivatives
spasmolytic activity
url http://www.degruyter.com/view/j/acph.2014.64.issue-2/acph-2014-0016/acph-2014-0016.xml?format=INT
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