78950-74-0Relevant academic research and scientific papers
2-Morpholinoisoflav-3-enes as flexible intermediates in the synthesis of phenoxodiol, isophenoxodiol, equol and analogues: Vasorelaxant properties, estrogen receptor binding and Rho/RhoA kinase pathway inhibition
Tilley, Andrew J.,Zanatta, Shannon D.,Qin, Cheng Xue,Kim, In-Kyeom,Seok, Young-Mi,Stewart, Alastair,Woodman, Owen L.,Williams, Spencer J.
experimental part, p. 2353 - 2361 (2012/05/07)
Isoflavone consumption correlates with reduced rates of cardiovascular disease. Epidemiological studies and clinical data provide evidence that isoflavone metabolites, such as the isoflavan equol, contribute to these beneficial effects. In this study we developed a new route to isoflavans and isoflavenes via 2-morpholinoisoflavenes derived from a condensation reaction of phenylacetaldehydes, salicylaldehydes and morpholine. We report the synthesis of the isoflavans equol and deoxygenated analogues, and the isoflavenes 7,4′-dihydroxyisoflav-3-ene (phenoxodiol, haganin E) and 7,4′-dihydroxyisoflav-2-ene (isophenoxodiol). Vascular pharmacology studies reveal that all oxygenated isoflavans and isoflavenes can attenuate phenylephrine-induced vasoconstriction, which was unaffected by the estrogen receptor antagonist ICI 182,780. Furthermore, the compounds inhibited U46619 (a thromboxane A2 analogue) induced vasoconstriction in endothelium-denuded rat aortae, and reduced the formation of GTP RhoA, with the effects being greatest for equol and phenoxodiol. Ligand displacement studies of rat uterine cytosol estrogen receptor revealed the compounds to be generally weak binders. These data are consistent with the vasorelaxation activity of equol and phenoxodiol deriving at least in part by inhibition of the RhoA/Rho-kinase pathway, and along with the limited estrogen receptor affinity supports a role for equol and phenoxodiol as useful agents for maintaining cardiovascular function with limited estrogenic effects.
The Enamine Route to 2-Morpholinoisoflav-3-ene
Dean, Francis M.,Varma, Rajender S.
, p. 1193 - 1196 (2007/10/02)
In contrast to earlier reports, the condensation of N-styrylmorpholine with salicylaldehyde or with 3-methoxysalicylaldehyde gives 2-morpholinoisoflav-3-ene derivatives. 2-Morpholinoisoflav-3-ene can be hydrogenolysed in a useful synthesis of isoflavan; with acids it gives in high yield a remarkably stable di(isoflavenyl)ether (6); with triphenylmethyl perchlorate it gives isoflavylium perchlorate.A similar condensation with N-(cyclohexenyl)morpholine behaves differently, giving alcohols that are oxidised to chromone (or tetrahydroxanthone) derivatives, in accord withprevious reports.
REVISION OF AN ENAMINE SYNTHESIS; THE PREPARATION AND REACTIONS OF 2-MORPHOLINOISOFLAV-3-ENE.
Dean, Francis M.,Varma, Rajender S.
, p. 2113 - 2114 (2007/10/02)
The condensation of N-styrylmorpholine with salicylaldehyde does not give a product that can be oxidised to isoflavone; the product is N-morpholino-isoflav-3-ene wich can be used to prepare other compounds related to isoflavan and upon oxidation gives 3-phenylcoumarin.
