Synthesis and hypolipidemic activity of modified side chain alpha-asarone homologues.
A series of homologues of alpha-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 I and olefins 10 suggest unfavorable steric interactions in the bulky superior side-chain homologues as the deactivating biological effect.
Cruz
A
A
Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, México, D.F., Mexico.
Garduño
L
L
Salazar
M
M
Martínez
E
E
Jiménez-Vázquez
H A
HA
Díaz
F
F
Chamorro
G
G
Tamariz
J
J
D000081248:Allylbenzene Derivatives; D000818:Animals; D000840:Anisoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D002791:Cholesterol, Dietary / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004032:Diet; D004435:Eating / Q000187:drug effects; D000960:Hypolipidemic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D008297:Male; D051379:Mice; D008958:Models, Molecular; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship; D015430:Weight Gain / Q000187:drug effects
D000081248:Allylbenzene Derivatives; D000840:Anisoles; D002791:Cholesterol, Dietary; D000960:Hypolipidemic Agents; C012195:asarone