Synthesis, X-ray diffraction study and pharmacological evaluation of 3-amino-4-methylthiophene-2-acylcarbohydrazones
| Autor: | Morgana Vital de Araújo, Lídia Moreira Lima, Fanny N. Costa, Fabio Furlan Ferreira, Magna Suzana Alexandre-Moreira, Stefan Laufer, Thays de Lima Matos Freire Dias, Sonja Herrmann, Tabea Schübel, Maria Claudia Barbosa, Eliezer J. Barreiro |
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| Rok vydání: | 2018 |
| Předmět: |
Double bond
Imine Anti-Inflammatory Agents 010402 general chemistry p38 Mitogen-Activated Protein Kinases 01 natural sciences Mass Spectrometry privileged structure X-ray Mice chemistry.chemical_compound X-Ray Diffraction In vivo Animals Relative potency lcsh:Science chemistry.chemical_classification Analgesics Multidisciplinary 010405 organic chemistry Spectroscopy methods Hydrazones N-acylhydrazone Combinatorial chemistry antinociceptive 0104 chemical sciences chemistry Drug Design X-ray crystallography p38MAPK Common key lcsh:Q Divergent synthesis |
| Zdroj: | Anais da Academia Brasileira de Ciências v.90 n.1 suppl.2 2018 Anais da Academia Brasileira de Ciências Academia Brasileira de Ciências (ABC) instacron:ABC Anais da Academia Brasileira de Ciências, Volume: 90, Issue: 1 Supplement 2, Pages: 1073-1088, Published: 2018 Anais da Academia Brasileira de Ciências, Vol 90, Iss 1 suppl 2, Pp 1073-1088 |
| ISSN: | 1678-2690 0001-3765 |
| Popis: | N-acylhydrazone is an interesting privileged structure that has been used in the molecular design of a myriad of bioactive compounds. In order to identify new antinociceptive drug candidates, we described herein the design, synthesis, X-ray diffraction study and the pharmacological evaluation of a series of 3-amino-4-methylthiophene-2-acylcarbohydrazone derivatives (8a-t). Compounds were prepared in good overall yields through divergent synthesis from a common key intermediate and were characterized by classical spectroscopy methods. X-ray diffraction study was employed for unequivocal determination of the imine double bond stereochemistry. 8a-t were evaluated in vivo through oral administration using the classical writhing test in mice. N-acylhydrazone derivatives 8j and 8l displayed relative potency similar to dipyrone, highlighting them as promising analgesic lead-candidates for further investigation. |
| Databáze: | OpenAIRE |
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