76252-27-2Relevant academic research and scientific papers
An effective system to synthesize hypolipidemic active α-asarone and related methoxylated (E)-arylalkenes
Sharma, Anuj,Joshi, Bhupendra P.,Sinha, Arun K.
, p. 2231 - 2235 (2004)
Methoxylated (E)-arylalkenes (1a-1k) were prepared in two steps by an improved Grignard reaction comprising the reverse addition of alkylmagnesium bromide to benzaldehydes (2a-2k) in anhydrous ether and toluene into arylalkanols (3a-3k) in high yield, followed by dehydration with silica gel under microwave irradiation for 3-12 min, depending upon the substituents attached to the aromatic ring to afford hypolipidemic active α-asarone (1a) and related methoxylated (E)-arylalkenes (1b-1k).
Ultrasound-assisted convenient synthesis of hypolipidemic active natural methoxylated (E)-arylalkenes and arylalkanones
Joshi, Bhupendra P.,Sharma, Anuj,Sinha, Arun K.
, p. 3075 - 3080 (2007/10/03)
An ultrasound-assisted convenient method was developed for the conversion of toxic methoxylated cis-isomer of arylalkenes into its hypolipidemic active trans-isomer. Treatment of cis-isomer or mixture of all three isomers (1a-1j) with ammonium formate and 10% Pd/C gave arylalkanes (2a-2j), which upon oxidation with DDQ in anhydrous dioxane containing a little amount of silica gel, provided (E)-arylalkenes (3a-3g) in 42-72% yield depending upon the substituents attached at the aryl ring. The same method, upon addition of a few drops of water, provided hypolipidemic active arylalkanones (3h-3j) in 59-65% yield.
Synthesis and hypolipidemic activity of modified side chain α-asarone homologues
Cruz,Garduno,Salazar,Martinez,Jimenez-Vazquez,Diaz,Chamorro,Tamariz
, p. 535 - 544 (2007/10/03)
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.
