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

Title: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

Volume: 14 Issue: 5

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

Affiliation:

• N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue, 9, 630090 Novosibirsk,Russian Federation

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

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.

Cite this article as:

Pavlova Alla, Patrusheva Oksana, Il`ina Irina, Volcho Konstantin*, Tolstikova Tat`yana and Salakhutdinov Nariman, 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, Letters in Drug Design & Discovery 2017; 14 (5) . https://dx.doi.org/10.2174/1570180813666161102142642

DOI https://dx.doi.org/10.2174/1570180813666161102142642	Print ISSN 1570-1808
Publisher Name Bentham Science Publisher	Online ISSN 1875-628X