The Decisive Role of Mutual Arrangement of Hydroxy and Methoxy Groups in (3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8ahexahydro- 2H-chromene-4,8-diols in their Biological Activity

Author(s): Alla Pavlova, Oksana Patrusheva, Irina Il`ina, Konstantin Volcho*, Tat`yana Tolstikova, Nariman Salakhutdinov.

Journal Name: Letters in Drug Design & Discovery

Volume 14 , Issue 5 , 2017

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Abstract:

Background: The positional effects of the methoxy- and hydroxyl substituents in the phenyl ring were examined in vivo for distinct receptor classes in order to gain an insight into the mechanism by which isomeric compounds (2S,4R,4aR,8R,8aR)-2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl- 3,4,4a,5,8, 8a-hexahydro-2H-chromene-4,8-diols 1 and 2 exhibit their pharmacological activity.

Conclusion: Our findings suggest a strong structure-function relationship between the substitution pattern and the mechanism of biological activity of compound. The methoxy substituent at C4 and the hydroxyl substituent at C3 (compound 1) seem to employ the cannabinoid and adrenergic systems, whereas compound 2 with the methoxy substituent at C3 and the hydroxyl substituent at C4 possibly targets the opioid and dopaminergic mechanisms.

Keywords: Analgesia, monoterpenoids, CB1 receptors, opioid receptors, adrenergic system, dopaminergic system.

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Article Details

VOLUME: 14
ISSUE: 5
Year: 2017
Page: [508 - 514]
Pages: 7
DOI: 10.2174/1570180813666161102142642
Price: $65

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