Mannich-type modifications of (−)-cannabidiol and (−)-cannabigerol leading to new, bioactive derivatives

Lőrincz, Eszter Boglárka and Tóth, Gergely and Spolárics, Júlia and Herczeg, Mihály and Hodek, Jan and Zupkó, István and Minorics, Renáta and Ádám, Dorottya and Oláh, Attila and Zouboulis, Christos C. and Weber, Jan and Nagy, Lajos and Ostorházi, Eszter and Bácskay, Ildikó and Borbás, Anikó and Herczegh, Pál and Bakai-Bereczki, Ilona (2023) Mannich-type modifications of (−)-cannabidiol and (−)-cannabigerol leading to new, bioactive derivatives. SCIENTIFIC REPORTS, 13 (1). No. 19618. ISSN 2045-2322

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Abstract

(−)-Cannabidiol (CBD) and (−)-cannabigerol (CBG) are two major non-psychotropic phytocannabinoids that have many beneficial biological properties. However, due to their low water solubility and prominent first-pass metabolism, their oral bioavailability is moderate, which is unfavorable for medicinal use. Therefore, there is a great need for appropriate chemical modifications to improve their physicochemical and biological properties. In this study, Mannich-type reaction was used for the synthetic modification of CBD and CBG for the first time, and thus fifteen new cannabinoid derivatives containing one or two tertiary amino groups were prepared. Thereafter the antiviral, antiproliferative and antibacterial properties of the derivatives and their effects on certain skin cells were investigated. Some modified CBD derivatives showed remarkable antiviral activity against SARS-CoV-2 without cytotoxic effect, while synthetic modifications on CBG resulted in a significant increase in antiproliferative activity in some cases compared to the parent compound.

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