Síntese e avaliação da atividade antioxidante de derivados e análogos do canabidiol

Abstract

Cannabis is a general name given to plants of the Cannabis sp. genus, of the Cannabaceae family, used as therapeutic, religious, spiritual, narcotic and recreational input for millennia. It has dozens of substances called phytocannabinoids, including Δ9 -tetrahydrocannabinol, responsible for the characteristic psychoactivity of cannabis, and cannabidiol, a non-psychoactive phytocannabinoid with several therapeutic activities described and under investigation, such as analgesic, anti-inflammatory, antioxidant, neuroprotective, anticonvulsant and antispasmodic activities. Cannabidiol, however, has unfavorable physicochemical characteristics for oral administration, such as high hydrophobicity that directly influences its solubility and consequent absorption, in addition to extensive hepatic metabolism. In order to obtain more water-soluble and more potent substances, 16 substances were synthesized in this work, including derivatives and analogues of cannabidiol and olivetol. Their antioxidant activities were evaluated in two different in vitro assays, the DDPH and ABTS.+. Three substances, 4, 8 and 9, showed, in general, activity comparable to cannabidiol in both tests and one of them, 6, showed activity superior to cannabidiol and to the positive control in the DDPH assay. None of the synthesized substances was, however, capable of performing an activity greater than 50% in the tests for antioxidant activity.