Labedipinedilol A
Chemical Name: 4-[4-[2-Hydroxy-3-[2-(2-methoxyphenoxy)ethylamino]propoxy]-3-methoxyphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester
CAS No. 257284-30-3
项目整合开发状态: Preclinical
项目研究机构: Kaohsiung Medical University (Originator)
合成路线:Guaiacol (I) was alkylated by means of boiling dibromoethane (II) to produce the bromoethyl ether (III).From this,the intermediate amine (VI) was prepared by Gabriel synthesis,via condensation with potassium phthalimide (IV) in hot DMF,followed by hydrazinolysis of the resultant N-substituted phthalimide (V).
合成路线:The condensation of vanillin (VII) with epichlorohydrin (VIII) in ethanolic NaOH produced the glycidyl ether (IX).Epoxide ring opening in (IX) by means of amine (VI) in EtOH furnished amino alcohol (X).The title dihydropyridine derivative was then obtained by reaction between aldehyde (X),methyl acetoacetate (XI),and ammonia under Hantzsch condensation conditions.
📌 参考资料/链接：
参考文献标题:Guaiacoxypropanolamines with alpha/beta-adrenergic blocking activity
文献作者:Lin,T.-H.; Chen,I.-J.
参考来源:EP 1108710; WO 0005209
📄 详细内容
合成路线:The condensation of vanillin (I) with epichlorohydrin (II) in ethanolic NaOH produced the glycidyl ether (III).Epoxide ring opening in (III) by means of tert-butylamine (IV) in EtOH furnished amino alcohol (V).The title dihydropyridine derivative was then obtained by reaction between aldehyde (V),methyl acetoacetate (VI),ammonia under Hantzsch condensation conditions,and was isolated after conversion to the hydrochloride salt.
合成路线:The condensation of vanillin (VII) with epichlorohydrin (VIII) in ethanolic NaOH produced the glycidyl ether (IX).Epoxide ring opening in (IX) by means of amine (VI) in EtOH furnished amino alcohol (X).The title dihydropyridine derivative was then obtained by reaction between aldehyde (X),methyl acetoacetate (XI),and ammonia under Hantzsch condensation conditions.
参考文献标题:The new generation dihydropyridine type calcium blockers,bearing 4-phenyl oxypropanolamine,display alpha-/beta-adrenoceptor antagonist and long-acting antihypertensive activities
文献作者:Liang,J.-C.; Chen,I.-J.; Wang,C.-S.; Liou,S.-F.; Tsai,C.-H.; Yeh,J.-L.
参考来源:Bioorg Med Chem 2002,10(3),719