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

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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. / Patrusheva, O. S.; Pavlova, A. V.; Korchagina, D. V. et al.

In: Chemistry of Natural Compounds, Vol. 53, No. 6, 01.11.2017, p. 1066-1071.

Research output: Contribution to journal › Article › peer-review

Author

Patrusheva, O. S. ; Pavlova, A. V. ; Korchagina, D. V. et al. / 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. In: Chemistry of Natural Compounds. 2017 ; Vol. 53, No. 6. pp. 1066-1071.

BibTeX

@article{d14667c49add44e3a38e9b486507e5f7,

title = "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",

abstract = "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.",

keywords = "aldehydes, analgesic activity, heterocyclic compounds, monoterpenes, montmorillonite clay",

author = "Patrusheva, {O. S.} and Pavlova, {A. V.} and Korchagina, {D. V.} and Tolstikova, {T. G.} and Volcho, {K. P.} and Salakhutdinov, {N. F.}",

year = "2017",

month = nov,

day = "1",

doi = "10.1007/s10600-017-2202-1",

language = "English",

volume = "53",

pages = "1066--1071",

journal = "Chemistry of Natural Compounds",

issn = "0009-3130",

publisher = "Springer New York",

number = "6",

}

RIS

TY - JOUR

T1 - 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

AU - Patrusheva, O. S.

AU - Pavlova, A. V.

AU - Korchagina, D. V.

AU - Tolstikova, T. G.

AU - Volcho, K. P.

AU - Salakhutdinov, N. F.

PY - 2017/11/1

Y1 - 2017/11/1

N2 - 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.

AB - 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.

KW - aldehydes

KW - analgesic activity

KW - heterocyclic compounds

KW - monoterpenes

KW - montmorillonite clay

UR - http://www.scopus.com/inward/record.url?scp=85034632451&partnerID=8YFLogxK

U2 - 10.1007/s10600-017-2202-1

DO - 10.1007/s10600-017-2202-1

M3 - Article

AN - SCOPUS:85034632451

VL - 53

SP - 1066

EP - 1071

JO - Chemistry of Natural Compounds

JF - Chemistry of Natural Compounds

SN - 0009-3130

IS - 6

ER -

ID: 8969001