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Acta Pharmaceutica

The Journal of Croatian Pharmaceutical Society

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Volume 64, Issue 2

Issues

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
  • Corresponding author
  • Centro de Educação e Saúde Universidade Federal de Campina Grande 58175-000, Cuité-PB, Brazil
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Thiago M. De Aquino
  • Instituto de Química e Biotecnologia Universidade Federal de Alagoas 57072-970, Maceió-AL, Brazil
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  • De Gruyter OnlineGoogle Scholar
/ Bruno F. Lira / Petrônio F. A. Filho / Marcus T. Scotti
  • Departamento de Engenharia e Meio Ambiente, Universidade Federal da Paraíba Campus IV, 58297-000, Rio Tinto-PB, Brazil
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  • De Gruyter OnlineGoogle Scholar
/ Luciana Scotti
  • Departamento de Ciências Biológicas Universidade Estadual da Paraíba CCBSA, João Pessoa-PB 58070-450 Brazil
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  • De Gruyter OnlineGoogle Scholar
/ Ricardo O. De Moura
  • Departamento de Ciências Biológicas Universidade Estadual da Paraíba CCBSA, João Pessoa-PB 58070-450 Brazil
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  • De Gruyter OnlineGoogle Scholar
/ Francisco J. B. Mendonça Junior
Published Online: 2014-06-06 | DOI: https://doi.org/10.2478/acph-2014-0016

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, 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

References

  • 1. L. B. Kier and E. B. Roche, Medicinal chemistry of the mesoionic compounds, J. Pharm. Sci. 56 (1966) 149-168; DOI: 10.1002/jps.2600560202.CrossrefGoogle Scholar

  • 2. M. B. Oliveira, J. Miller, A. B. Pereira, S. E. Galembeck, G. L. C. Moura and A. M. Simas, Mesoionic 2-N-cycloalkylamino-5-alkyl-1,3-dithiolium-4-thiolates, Phosphorus, Sulfur, Silicon Relat. Elem. 108 (1996) 75-84; DOI: 10.1080/10426509608029640.CrossrefGoogle Scholar

  • 3. C. A. C. Bosco, G. S. Maciel, N. Rakov, C. B. Araújo, L. H. Acioli, A. M. Simas, P. F. Athayde- -Filho and J. Miller, Probing the nuclear susceptibility of mesoionic compounds using two-beam coupling with chirp-controlled pulses, Chem. Phys. Lett. 449 (2007) 101-106; DOI: 10.1016/ j.cplett.2007.10.037.Web of ScienceCrossrefGoogle Scholar

  • 4. R. S. T. R. Nascimento, C. R. S. Morais, H. L. Lira, S. A. Morais, P. F. Athayde-Filho, L. F. L. Lucena, A. G. Souza and G. B. Campos, Synthesis and characterization of nanocomplexes of Eu(III) and Er(III) coordinate with 2(4-clorophenyl)-3-phenyl-1,3,4-thiadiazoleo-5-tiolate mesoionic, J. Alloys Comp. 495 (2010) 603-605; DOI: 10.1016/j.jallcom.2009.12.003.Web of ScienceCrossrefGoogle Scholar

  • 5. S. A.Morais, C. R. S. Morais, P. F. Athayde-Filho, B. F. Lira and R. S. T. R. Nascimento, Akinetic study of the thermal decomposition of mesoionic compounds within scope of its application in nonlinear optical devices, J. Therm. Anal. Calorim. 97 (2009) 437-441; DOI: 10.1007/s10973-009-0082-8.Web of ScienceCrossrefGoogle Scholar

  • 6. B. F. Lira, S. A. Morais, G. B. Rocha, J. Miller, G. L. C. Moura, A. M. Simas, C. Peppe and P. F. Athayde-Filho, 1,3-Thiazolium-5-thiolates mesoionic compounds: Semiempirical evaluation of their first static hyperpolarizabilities and synthesis of new examples, J. Braz. Chem. Soc. 21 (2010) 934-940; DOI: 101590/S0103-505320100000500024.Web of ScienceGoogle Scholar

  • 7. A. S.-Ribeiro, A. Echevarria, E. F. Silva, C. R. C. Franco, S. S. Veiga and M. B. M. Oliveira, Cytotoxic effect of a new 1,3,4-thiadiazolium mesoionic compound (MI-D) on cell lines of human melanoma, Br. J. Cancer 91 (2004) 297-304. DOI: 10.1038/sj.bjc.6601946.CrossrefGoogle Scholar

  • 8. R. F. Rodrigues, E. F. Silva, A. Echevarria, R. Fajardo-Bonin, V. F. Amaral, L. L. Leon and M. M. Canto-Cavalheiro, A comparative study of mesoionic compounds in Leishmania sp. and toxicity evaluation, Eur. J. Med. Chem. 42 (2007) 1039-1043; DOI: 10.1016/j.ejmech.2006.12.026.CrossrefWeb of ScienceGoogle Scholar

  • 9. R. F. Rodrigues, D. Castro-Pinto, A. Echevarria, C.M. Reis, C. N. Del Cistia, C. M. R. Sant’Anna, F. Teixeira, H. Castro, M. Canto-Cavalheiro, L. L. Leon and A. Tomás, Investigation of tripanothione redutase inhibitory activity by 1,3,4-thiadiazolium-2-aminide derivatives and molecular docking studies, Bioorg. Med. Chem. 20 (2012) 1760-1766; DOI: 10.1016/j.bmc.2012.01.009.CrossrefWeb of ScienceGoogle Scholar

  • 10. K. L. M. Cavalcante, N. A. Correia, K. L. G. Dias, D. F. Silva, J. C. Silva-Filho, I. G. A. Araújo, B. F. Lira, P. F. Athayde-Filho and I. A. Medeiros, Endothelium-derived nitric oxide contributes to the vasorelaxant response induced by mesoionic 2-(4-chlorophenyl)-3-methyl-4-(4-methoxyphenyl)-1,3-thiazolium-5-thyolate (CMMTT) in rats, J. Pharmacol. Sci. 110 (2009) 29-35; DOI: 10.1254/jphs.FP0071581.CrossrefWeb of ScienceGoogle Scholar

  • 11. K. Rehse, T. Ciborski and B. Müller, Platelet aggregation inhibiting and anticoagulant effects of oligoamines. XXVII. Inhibition of leucocyte adherence to endothelium by oligoamine RE 1492C and the NO-donor RE 2047, Arch. Pharm. (Weinheim) 328 (1995) 125-126; DOI: 10.1002/ardp. 19953280206.CrossrefGoogle Scholar

  • 12. L. B. Kier and E. B. Roche, Medicinal chemistry of the mesoionic compounds, J. Pharm. Sci. 56 (1967) 149-168; DOI: 10.1002/jps.2600560202.CrossrefGoogle Scholar

  • 13. C. S. Oliveira, V. S. Falcão-Silva, J. P. Siqueira-Júnior, D. P. Harding, B. F. Lira, J. G. F. Lorenzo, J. M. Barbosa-Filho and P. F. Athayde-Filho, Drug resistance modulation in Staphylococcus aureus, a new biological activity for mesoionic hydrochloride compounds, Molecules 16 (2011) 2023-2031; DOI: 10.3390/molecules16032023.CrossrefWeb of ScienceGoogle Scholar

  • 14. B. F. Lira, J. Miller, A. M. Simas, P. F. Athayde-Filho, A. F. Dias, R. O. Silva and V. C. Oliveira, Synthesis and complete assignments of 1H and 13C-NMR spectra of mesoionic 2-(p-trifluoromethylphenyl)-3-methyl-4-(p-tolyl)-1,3-thiazolium-5-thiolate and 2-(p-chlorophenyl)-3-methyl-4-(p-isopropylphenyl)-1,3-thiazolium-5-thiolate, Arkivoc vi (2004) 12-21.Google Scholar

  • 15. P. F. Athayde-Filho, J. Miller, A. M. Simas, K. X. F. R. Sena and A. A. Chiappeta, Synthesis, characterization and evaluation of the activity of ten mesoionic compounds against microorganisms, Lat. Am. J. Pharm. 18 (1999) 17-22. Google Scholar

  • 16. J. T. Lima J. R. G. S. Almeida, K. S. L.Mota, A. S. S. C. Lúcio, C. A. Câmara, J.M. B. Filho and B. A. Silva, Selective spasmolytic effect of a new furanoflavoquinone derivative from diplotropin on guinea-pig trachea, J. Chem. Pharm. Res. 3 (2011) 249-258.Google Scholar

  • 17. E. E. Daniel, C. Y. Kwan and L. Janssen, Pharmacological techniques for the in vitro study of intestinal smooth muscles, J. Pharmacol. Toxicol. Meth. 45 (2001) 141-158.Google Scholar

  • 18. B. M. Altura and B. T. Altura, Differential effects of substrate depletion on drug-induced contractions of rabbit aorta, Am. J. Physiol. 219 (1970) 1698-1705.Google Scholar

  • 19. E. Tschirhart, N. Frossard, C. Bertrand and Y. Landry, Arachidonic acid metabolites and airway epithelium-dependent relaxant factor, J. Pharmacol. Exp. Ther. 243 (1987) 310-316. Google Scholar

About the article

Accepted: 2014-01-21

Published Online: 2014-06-06

Published in Print: 2014-06-01


Citation Information: Acta Pharmaceutica, Volume 64, Issue 2, Pages 233–245, ISSN (Online) 1846-9558, ISSN (Print) 1330-0075, DOI: https://doi.org/10.2478/acph-2014-0016.

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© by José A. S. Luis. This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. BY-NC-ND 3.0

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