【药物名称】Murabutide
化学结构式(Chemical Structure):
参考文献No.42025
标题:Novel compounds of the muramyl peptide
作者:Lefrancier, P.; Parant, M.; Audibert, F.; Chedid, L.; Choay, J.; Lederer, E. (ANVAR (Agence Natl. Valor. Rech.))
来源:DD 145274; EP 0006068; ES 481785; FR 2428051; JP 55000392; US 4693998
合成路线图解说明:

The reaction of N-benzltoxycarbonyl-L-alanine succinimidyl ester (I) with o-glutamine (II) by means of triethylamine in THF water gives benzyloxycarbonyl-L-alanyl-o-glutamine (III), which is esterified with bromobutane and Cs2CO3 in DMF yielding the corresponding butyl ester (IV). Deprotection of (IV) by hydrogenation with H2 over Pd/C in acetic acid affords L-alanyl-D-glutamine n-butyl ester (V), which is condensed with 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramic acid (VI) bv the mixed anhydride method affording 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramyl-L-alanyl-o-glutamine n-butyl ester (VII). Finally, this compound is deprotected by hydrogenation with H2 over Pd/C as before.

参考文献No.71739
标题:Murabutide
作者:Casta馿r, J.; Prous, J.
来源:Drugs Fut 1986,11(9),750
合成路线图解说明:

The reaction of N-benzltoxycarbonyl-L-alanine succinimidyl ester (I) with o-glutamine (II) by means of triethylamine in THF water gives benzyloxycarbonyl-L-alanyl-o-glutamine (III), which is esterified with bromobutane and Cs2CO3 in DMF yielding the corresponding butyl ester (IV). Deprotection of (IV) by hydrogenation with H2 over Pd/C in acetic acid affords L-alanyl-D-glutamine n-butyl ester (V), which is condensed with 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramic acid (VI) bv the mixed anhydride method affording 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramyl-L-alanyl-o-glutamine n-butyl ester (VII). Finally, this compound is deprotected by hydrogenation with H2 over Pd/C as before.

参考文献No.555587
标题:Potential neuroleptic agents. 2,6-dialkoxybenzamide derivatives with potent dopamine receptor blocking activities
作者:Florvall, L.; Ogren, S.O.
来源:J Med Chem 1982,25(11),1280
合成路线图解说明:

The reaction of N-benzltoxycarbonyl-L-alanine succinimidyl ester (I) with o-glutamine (II) by means of triethylamine in THF water gives benzyloxycarbonyl-L-alanyl-o-glutamine (III), which is esterified with bromobutane and Cs2CO3 in DMF yielding the corresponding butyl ester (IV). Deprotection of (IV) by hydrogenation with H2 over Pd/C in acetic acid affords L-alanyl-D-glutamine n-butyl ester (V), which is condensed with 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramic acid (VI) bv the mixed anhydride method affording 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramyl-L-alanyl-o-glutamine n-butyl ester (VII). Finally, this compound is deprotected by hydrogenation with H2 over Pd/C as before.

合成路线图解说明:

The bromination of 2,6-dimethoxybenzoic acid (I) with Br2 in dioxane gives 3-bromo-2,6-dimethoxy benzoic acid (II), which is treated with refluxing SOCl2 yielding the corresponding acyl chloride (III). Finally, this compound is condensed with (-)-(S)-1-ethyl 2-(aminomethyl)pyrrolidine (IV).

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