Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols
- 308 Downloads
2-(3(4)-Hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols were found recently to possess high analgesic activity and low acute toxicity. Stereoisomers of these compounds with high optical purity were synthesized from (+)- and (−)-α-pinenes for the first time in this work. The structure of (4S)-4b isomer was confirmed by the XRD data. Studies of analgesic activity of the resulting products demonstrated that neither the absolute configuration nor cis- or trans-arrangement of vicinal oxygen atoms plays a significant role in manifestation of analgesic effect by these isomers, while only (4S)-4b isomer, but not (4R)-4b demonstrated the analgesic effect.
KeywordsTerpene Chromene Heterocyclic compounds Analgesic activity Acetic acid-induced writhing test Hot plate test Stereoisomers
Authors are grateful to the Russian Foundation for Basic Research (Grant No 13-03-00206a) for the financial support.
- Ardashov OV, Pavlova AV, Il’ina IV, Morozova EA, Korchagina DV, Karpova EV, Volcho KP, Tolstikova TG, Salakhutdinov NF (2011) Highly potent activity of (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in animal models of Parkinson’s disease. J Med Chem 54:3866–3874CrossRefPubMedGoogle Scholar
- Koster R, Anderson M, De Beer EJ (1959) Acetic acid for analgesic screening. Fed Proc 18:412–415Google Scholar
- Mikhalchenko OS, Volcho KP, Salakhutdinov NF (2013) Synthesis of heterocyclic compounds by interaction of aldehydes with monoterpenoids. In: Torrioni L, Pescasseroli E (eds) New developments in aldehydes research. Nova Science Publishers, NY, pp 49–80. ISBN: 978-1-62417-090-4Google Scholar