BIA-3-202
3-硝基-5-苯基乙酰基邻苯二酚Chemical Name: 1-(3,4-Dihydroxy-5-nitrophenyl)-2-phenyl-1-ethanone
CAS No. 274925-86-9
项目整合开发状态: Phase I
项目研究机构: Bial (Originator), Portela (Originator)
合成路线:Protection of vanillin (I) as the benzyl ether (II),followed by reaction with benzylmagnesium bromide,furnished alcohol (III).Oxidation of alcohol (III) to the corresponding ketone (IV) was achieved by means of chromium trioxide or,in an improved procedure,by Oppenauer oxidation with cyclohexanone and sodium tert-butoxide.Benzyl group cleavage in (IV) either with HBr,or by transfer hydrogenolysis,yielded phenol (V).Regioselective nitration of (V) gave the ortho-nitrophenol (VI).The title compound was finally obtained by methyl ether cleavage in (VI) with boiling HBr or with AlCl3 in pyridine.
📌 参考资料/链接：
参考文献标题:Substd.2-phenyl-1-(3,4-dihydroxy-5-nitrophenyl)-1-ethanones,their use in the treatment of some central and peripheral nervous system disorders and pharmaceutical compsns.containing them
文献作者:Benes,J.; Soares da Silva,P.M.V.A.; Learmonth,D.A.(Portela & Ca.,SA)
参考来源:EP 1010688; GB 2344819; WO 0037423
📄 详细内容
合成路线:Protection of vanillin (I) as the benzyl ether (II),followed by reaction with benzylmagnesium bromide,furnished alcohol (III).Oxidation of alcohol (III) to the corresponding ketone (IV) was achieved by means of chromium trioxide or,in an improved procedure,by Oppenauer oxidation with cyclohexanone and sodium tert-butoxide.Benzyl group cleavage in (IV) either with HBr,or by transfer hydrogenolysis,yielded phenol (V).Regioselective nitration of (V) gave the ortho-nitrophenol (VI).The title compound was finally obtained by methyl ether cleavage in (VI) with boiling HBr or with AlCl3 in pyridine.
参考文献标题:Synthesis of 1-(3,4-dihydroxy-5-nitrophenyl)-2-phenyl-ethanone and derivatives as potent and selective inhibitors of catechol-O-methyltransferase (COMT)
文献作者:Learmonth,D.; et al.
参考来源:16th Int Symp Med Chem (Sept 18 2000,Bologna) 2000,Abst PA-34
合成路线:Protection of vanillin (I) as the benzyl ether (II),followed by reaction with benzylmagnesium bromide,furnished alcohol (III).Oxidation of alcohol (III) to the corresponding ketone (IV) was achieved by means of chromium trioxide or,in an improved procedure,by Oppenauer oxidation with cyclohexanone and sodium tert-butoxide.Benzyl group cleavage in (IV) either with HBr,or by transfer hydrogenolysis,yielded phenol (V).Regioselective nitration of (V) gave the ortho-nitrophenol (VI).The title compound was finally obtained by methyl ether cleavage in (VI) with boiling HBr or with AlCl3 in pyridine.
参考文献标题:Synthesis of 1-(3,4-dihydroxy-5-nitrophenyl)-2-phenyl-ethanone and derivatives as potent and long-acting peripheral inhibitors of catechol-O-methyltransferase
文献作者:Learmonth,D.A.; Vieira-Coelho,M.A.; Benes,J.; Alves,P.C.; Borges,N.; Freitas,A.P.; Soares-da-Silva,P.
参考来源:J Med Chem 2002,45(3),685
产品链接: CAS No. 274925-86-9››