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

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

Journal

Letters in Drug Design and Discovery
ISSN: 1570-1808 , E-ISSN: 1875-628X

Output data

Year: 2017, Volume: 14, Number: 5, Pages: 508-514 Pages count : 7 DOI: 10.2174/1570180813666161102142642

Tags

Analgesia; monoterpenoids; CB1 receptors; opioid receptors; adrenergic system; dopaminergic system

Authors

Pavlova Alla ¹ , Patrusheva Oksana ¹ , Il'ina Irina ^1,2 , Volcho Konstantin ^1,2 , Tolstikova Tat'yana ¹ , Salakhutdinov Nariman ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Lavrentjev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova 2, Novosibirsk 630090, Russia

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-dimethyl3,4,4a, 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 C-4 and the hydroxyl substituent at C-3 (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.

Pavlova A. , Patrusheva O. , Il'ina I. , Volcho K. , Tolstikova T. , Salakhutdinov N.
The Decisive Role of Mutual Arrangement of Hydroxy and Methoxy Groups in (3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols in their Biological Activity
Letters in Drug Design and Discovery. 2017. V.14. N5. P.508-514. DOI: 10.2174/1570180813666161102142642 WOS Scopus

Published print:

Apr 6, 2017

Web of science	WOS:000399449900001
Scopus	2-s2.0-85019731394
OpenAlex	W2607080871