Synthesis and hypolipidemic activity of modified side chain α-asarone homologues

A. Cruz; L. Garduño; M. Salazar; E. Martínez; H. A. Jiménez-Vázquez; F. Díaz; G. Chamorro; J. Tamariz

doi:10.1055/s-0031-1300077

Synthesis and hypolipidemic activity of modified side chain α-asarone homologues

A. Cruz, L. Garduño, M. Salazar, E. Martínez, H. A. Jiménez-Vázquez, F. Díaz, G. Chamorro, J. Tamariz

Escuela Nacional de Ciencias Biológicas (ENCB)

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

22 Scopus citations

Abstract

A series of homologues of α-asarone (1), containing variable size and functionality on the side chain attached to the aromatic ring, has been subjected to a study of structure-activity relationship. For most of the prepared derivatives, either with a carbonyl (8a-8e), a hydroxy group (9a-9e), or with a conjugated double bond (10a-10d), significant effects on serum lipoprotein cholesterol, LDL-cholesterol, HDL-cholesterol and triglycerides were displayed. The results showed an enhancement of the hypocholesterolemic activity as the length of the chain is decreased. Theoretical conformational and electrostatic potential analyses of 1 and olefins 10 suggest unfavorable steric interactions in the bulky superior side-chain homologues as the deactivating biological effect.

Original language	English
Pages (from-to)	535-544
Number of pages	10
Journal	Arzneimittel-Forschung/Drug Research
Volume	51
Issue number	7
DOIs	https://doi.org/10.1055/s-0031-1300077
State	Published - 2001

Keywords

α-Asarone, conformational analysis, hypocholesterolemic effects, side-chain homologues

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10.1055/s-0031-1300077

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abstract = "A series of homologues of α-asarone (1), containing variable size and functionality on the side chain attached to the aromatic ring, has been subjected to a study of structure-activity relationship. For most of the prepared derivatives, either with a carbonyl (8a-8e), a hydroxy group (9a-9e), or with a conjugated double bond (10a-10d), significant effects on serum lipoprotein cholesterol, LDL-cholesterol, HDL-cholesterol and triglycerides were displayed. The results showed an enhancement of the hypocholesterolemic activity as the length of the chain is decreased. Theoretical conformational and electrostatic potential analyses of 1 and olefins 10 suggest unfavorable steric interactions in the bulky superior side-chain homologues as the deactivating biological effect.",

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T1 - Synthesis and hypolipidemic activity of modified side chain α-asarone homologues

AU - Cruz, A.

AU - Garduño, L.

AU - Salazar, M.

AU - Martínez, E.

AU - Jiménez-Vázquez, H. A.

AU - Díaz, F.

AU - Chamorro, G.

AU - Tamariz, J.

PY - 2001

Y1 - 2001

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AB - A series of homologues of α-asarone (1), containing variable size and functionality on the side chain attached to the aromatic ring, has been subjected to a study of structure-activity relationship. For most of the prepared derivatives, either with a carbonyl (8a-8e), a hydroxy group (9a-9e), or with a conjugated double bond (10a-10d), significant effects on serum lipoprotein cholesterol, LDL-cholesterol, HDL-cholesterol and triglycerides were displayed. The results showed an enhancement of the hypocholesterolemic activity as the length of the chain is decreased. Theoretical conformational and electrostatic potential analyses of 1 and olefins 10 suggest unfavorable steric interactions in the bulky superior side-chain homologues as the deactivating biological effect.

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DO - 10.1055/s-0031-1300077

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JF - Arzneimittel-Forschung/Drug Research

IS - 7

ER -

Synthesis and hypolipidemic activity of modified side chain α-asarone homologues

Abstract

Keywords

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