【药物名称】BIA-3-202
化学结构式(Chemical Structure):
参考文献No.43986
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
作者:Benes, J.; Soares da Silva, P.M.V.A.; Learmonth, D.A. (Portela & Ca., SA)
来源:EP 1010688; GB 2344819; WO 0037423
合成路线图解说明:

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No.592880
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)
作者:Learmonth, D.; et al.
来源:16th Int Symp Med Chem (Sept 18 2000, Bologna) 2000,Abst PA-34
合成路线图解说明:

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No.650873
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
作者:Learmonth, D.A.; Vieira-Coelho, M.A.; Benes, J.; Alves, P.C.; Borges, N.; Freitas, A.P.; Soares-da-Silva, P.
来源:J Med Chem 2002,45(3),685
合成路线图解说明:

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.

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