Synthesis, antineoplastic activity and in silico studies of (S)-N-(1-hydroxy-3-methylbutan-2-yl)-3-(p-tolyl)-1,2,4-oxadiazole-5-carboxamide
| Autor: | Jonh Anderson Macêdo Santos, Silvia Maria Souza, Juliano C. R. Freitas, Rodrigo Ribeiro Alves Caiana, Cláudia Laís Araújo Almeida Santos, Gardênia Carmem Gadelha Militão, Jucleiton J. R. Freitas |
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| Rok vydání: | 2021 |
| Předmět: |
Renewable Energy
Sustainability and the Environment medicine.drug_class Stereochemistry General Chemical Engineering In silico Oxadiazole Carboxamide General Chemistry Biochemistry chemistry.chemical_compound chemistry medicine General Earth and Planetary Sciences General Agricultural and Biological Sciences General Environmental Science |
| Zdroj: | Research Journal of Chemistry and Environment. 25:167-176 |
| ISSN: | 2278-4527 0972-0626 |
| DOI: | 10.25303/257rjce16721 |
| Popis: | The development of chemotherapy agents without side effects is a major challenge, since traditional medicines usually have undesirable properties such as high toxicity, resistance and low bioavailability. In this sense, computational methods play a crucial role in the discovery and optimization of new drugs, as they combine speed and efficiency with low cost. The 1,2,4-oxadiazoles are one of the main classes of heterocyclics due to their numerous biological applications. In this work, we report the synthesis, antineoplastic evaluation and in silico study of a new 1,2,4-oxadiazole. The (S)-N-(1-hydroxy-3-methylbutan-2-yl)-3-(p-toluyl)-1,2,4-oxadiazole-5-carboxamide was obtained after two reaction steps in excellent yield. Although it has shown low activity in relation to the MCF-7, HCT116 and HL60 tumor cell lines, the molecular docking study indicates that this compound acts in the colchicine site and can inhibit tubulin polymerization. From the calculation of pharmacokinetic properties by the SwissADME and Osiris Property Explorer programs, it is possible to infer that the compound meets the Lipinski rules presenting good oral bioavailability and low toxicity. |
| Databáze: | OpenAIRE |
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