【药物名称】Tolrestatin, Tolrestat, AY-27773, Alrestin, Lorestat, Alredase
化学结构式(Chemical Structure):
参考文献No.46053
标题:N-Naphtoylglycine derivatives
作者:Sestanj, K.; Abraham, N.A.; Bellini, F.; Treasurywala, A.; Humber, L.G. (Ayerst Laboratories Inc.)
来源:EP 0059596; JP 570158756; US 4391825
合成路线图解说明:

The reaction of 6-methoxy-5-(trifluoromethyl)naphthalene-1-carboxylic acid (I) with SOCl2 in refluxing DMF gives the corresponding acyl chloride (II), which is condensed with methyl N-methylglycinate (III) by means of hydroxybenzotriazole and dicyclohexylcarbodiimide in DMF yielding methyl N-[[5-(trifluoromethyl)-6-methoxy-1-naphthyl]carbonyl]-N-methylglycinate (IV). The reaction of (IV) with P2S5 refluxing pyridine affords methyl N-[[5-(trifluoromethyl)-6-methoxy-1-naphthyl]thioxomethyl]-N-methylglycinate (V), which is finally hydrolyzed with NaOH in methanol water. The synthesis of [14C]-labeled tolrestat has also been described.

参考文献No.71713
标题:Tolrestat
作者:Casta馿r, J.; Serradell, M.N.
来源:Drugs Fut 1984,9(9),670
合成路线图解说明:

The reaction of 6-methoxy-5-(trifluoromethyl)naphthalene-1-carboxylic acid (I) with SOCl2 in refluxing DMF gives the corresponding acyl chloride (II), which is condensed with methyl N-methylglycinate (III) by means of hydroxybenzotriazole and dicyclohexylcarbodiimide in DMF yielding methyl N-[[5-(trifluoromethyl)-6-methoxy-1-naphthyl]carbonyl]-N-methylglycinate (IV). The reaction of (IV) with P2S5 refluxing pyridine affords methyl N-[[5-(trifluoromethyl)-6-methoxy-1-naphthyl]thioxomethyl]-N-methylglycinate (V), which is finally hydrolyzed with NaOH in methanol water. The synthesis of [14C]-labeled tolrestat has also been described.

参考文献No.608345
标题:N-[[5-(Trifluoromethyl)-6-methoxy-1-naphthalenyl]thioxomethyl]-N-methylglycine (tolrestat), a potent, orally active aldose reductase inhibitor
作者:Sestanj, K.; Bellini, F.; Fung, S.; Abraham, N.A.; Treasurywala, A.; Humber, L.G.; Simar-Duquesne, N.; Dvornik, D.
来源:J Med Chem 1984,27(43),255-256
合成路线图解说明:

The reaction of 6-methoxy-5-(trifluoromethyl)naphthalene-1-carboxylic acid (I) with SOCl2 in refluxing DMF gives the corresponding acyl chloride (II), which is condensed with methyl N-methylglycinate (III) by means of hydroxybenzotriazole and dicyclohexylcarbodiimide in DMF yielding methyl N-[[5-(trifluoromethyl)-6-methoxy-1-naphthyl]carbonyl]-N-methylglycinate (IV). The reaction of (IV) with P2S5 refluxing pyridine affords methyl N-[[5-(trifluoromethyl)-6-methoxy-1-naphthyl]thioxomethyl]-N-methylglycinate (V), which is finally hydrolyzed with NaOH in methanol water. The synthesis of [14C]-labeled tolrestat has also been described.

参考文献No.800094
标题:Synthesis of [14C]-labelled tolrestat (N-[[5-(trifluoromethyl)-6-methoxy-1-naphthalenyl]-[14C]thioxomethyl]-N-methylglycine
作者:Hicks, D.R.
来源:J Label Compd Radiopharm 1984,21(3),229-236
合成路线图解说明:

The reaction of 6-methoxy-5-(trifluoromethyl)naphthalene-1-carboxylic acid (I) with SOCl2 in refluxing DMF gives the corresponding acyl chloride (II), which is condensed with methyl N-methylglycinate (III) by means of hydroxybenzotriazole and dicyclohexylcarbodiimide in DMF yielding methyl N-[[5-(trifluoromethyl)-6-methoxy-1-naphthyl]carbonyl]-N-methylglycinate (IV). The reaction of (IV) with P2S5 refluxing pyridine affords methyl N-[[5-(trifluoromethyl)-6-methoxy-1-naphthyl]thioxomethyl]-N-methylglycinate (V), which is finally hydrolyzed with NaOH in methanol water. The synthesis of [14C]-labeled tolrestat has also been described.

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