Synthesis and Analgesic Activity of 4,7-Dimethyl-3,4,4a,5,8,8a-Hexahydro-2-Chromen-4,8-Diols Containing Alkyl-Substituted Aromatic Moieties

Synthesis and Analgesic Activity of 4,7-Dimethyl-3,4,4a,5,8,8a-Hexahydro-2-Chromen-4,8-Diols Containing Alkyl-Substituted Aromatic Moieties Full article

Journal

Chemistry of Natural Compounds
ISSN: 0009-3130 , E-ISSN: 1573-8388

Output data

Year: 2017, Volume: 53, Number: 6, Pages: 1066-1071 Pages count : 6 DOI: 10.1007/s10600-017-2202-1

Tags

monoterpenes; aldehydes; montmorillonite clay; heterocyclic compounds; analgesic activity

Authors

Patrusheva O.S. ¹ , Pavlova A.V. ¹ , Korchagina D.V. ¹ , Tolstikova T.G. ¹ , Volcho K.P. ^1,2 , Salakhutdinov N.F. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Prosp Akad Lavrenteva, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk Natl Res State Univ, 2 Pirogova St, Novosibirsk 630090, Russia

A series of new heterocyclic compounds with the hexahydro-2H-chromene skeleton were prepared by reacting the monoterpenoid para-mentha-1,8-diene-5,6-diol with 4-alkyl-substituted aromatic aldehydes. Adding small alkyl substituents (methyl and ethyl) to the aldehyde aromatic ring increased the yields of hexahydrochromenes as compared with the analogous reaction with benzaldehyde. However, adding a branched substituent (isopropyl) and longer butyl and octyl moieties reduced the yields of the target compounds. The stereoselectivity of the reaction changed as the alkyl substituent lengthened. The analgesic activity of the obtained products was studied.

Patrusheva O.S. , Pavlova A.V. , Korchagina D.V. , Tolstikova T.G. , Volcho K.P. , Salakhutdinov N.F.
Synthesis and Analgesic Activity of 4,7-Dimethyl-3,4,4a,5,8,8a-Hexahydro-2-Chromen-4,8-Diols Containing Alkyl-Substituted Aromatic Moieties
Chemistry of Natural Compounds. 2017. V.53. N6. P.1066-1071. DOI: 10.1007/s10600-017-2202-1 WOS Scopus РИНЦ

Published print:	Nov 1, 2017
Published online:	Nov 22, 2017

Web of science	WOS:000416801100012
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