Design and Synthesis of Two Methylthiosteroid-Oxirenol Derivatives: Theoretical ‎Evaluation of Their Interaction with B1-Cannabinoid Receptor

Figueroa-Valverde Lauro , Diaz-Cedillo Francisco , Rosas-Nexticapa Marcela , Garcimarero-Espino E. ‎Alejandra , Mateu-Armand Virginia , Lopez-Ramos Maria , Hau-Heredia-Lenin , Estrella- Barron Raquel , ‎Borges-Ballote Yaritza


Several agonists and antagonists of B1 cannabinoid receptors have been synthesized for the treatment of several clinical pathologies such as psychosis, hyperalgesia, and drug addiction; however, some of these drugs may produce some side effects including higher intraocular pressure, hepatotoxicity, etc. The aim of this study was to synthesize two new methylthiosteroid-oxirenol derivatives (compounds 7 and 8) to evaluate their theoretical interaction with B1 cannabinoid receptor (5gtz) using WIN-55,212-2, yangonin, cannabigerol, and tetrahydrocannabivarin drugs as controls in a docking model. The preparation of 7 and 8 were carried out using a series of reactions which involved nitration, etherification, hydrogenation-chlorination, and addition. The chemical structure of the compounds was confirmed using elemental analysis and NMR spectrum. The results showed that compound 7 or 8 could bind to different types of amino acid residues involved in 5gtz protein surface compared with the WIN 55,212-2, Yangonin, Cannabigerol, and Tetrahydrocannabivarin drugs. All data suggest that compound 7 or 8 may exert changes in the biological activity of B1 cannabinoid receptor‎‎.

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