NSC-706995, MS-275, MS-27-275
恩替诺特 氨基酸,[[4-[[(2-氨基苯基)氨基]苯基]甲基,3-吡啶甲酯,盐酸盐 Chemical Name: N-[4-[N-(2-Aminophenyl)carbamoyl]benzyl]carbamic acid 3-pyridylmethyl ester
CAS No. 209783-80-2, 209784-80-5 (monoHCl)
项目整合开发状态: Phase II
项目研究机构: Mitsui Pharmaceuticals (Originator), Schering AG (Originator), National Cancer Institute (Codevelopment)
合成路线:The acylation of 4-(aminomethyl)benzoic acid (I) with trifluoroacetic anhydride gives the corresponding trifluoroacetamide (II),which is condensed with the monoprotected ortho-phenylenediamine (III) by means of oxalyl chloride in dichloromethane/DMF yielding the benzamide (IV).Elimination of the trifluoacetyl group of (V) by means of K2CO3 in methanol/water affords the 4-(aminomethyl)-derivative (V),which is condensed with 3-(hydroxymethyl)pyridine (VI) and carbonyldiimidazole (CDI) in THF providing the Boc-protected intermediate (VII).Finally,this compound is deprotected by a treatment with 4N HCl in dioxane/water.
📌 参考资料/链接：
参考文献标题:Benzamide derivs.,useful as cell differentiation inducers
文献作者:Suzuki,T.; Ando,T.; Tsuchiya,K.; Nakanishi,O.; Saito,A.; Yamashita,T.; Shiraishi,Y.; Tanaka,E.(Mitsui Chemicals,Inc.)
参考来源:EP 0847992
📄 详细内容
合成路线:The reaction of 4-(aminomethyl)benzoic acid (I) with 3-pyridinylmethanol (II) and CDI by means of DBU and TEA in THF gives the carbamate (III),which is treated with oxalyl chloride in toluene to yield the corresponding acyl chloride (IV).Finally,the condensation of (IV) with 1,2-phenylenediamine (V) by means of imidazole in THF affords the target compound.Alternatively,the condensation of acyl chloride (IV) with 2-nitroaniline (VI) by means of pyridine gives the corresponding amide (VII),which is finally reduced with SnCl2 and ammonium acetate in methanol.
参考文献标题:Synthesis and histone deacetylase inhibitory activity of new benzamide derivatives
文献作者:Suzuki,T.; Ando,T.; Tsuchiya,K.; Fukazawa,N.; Saito,A.; Mariko,Y.; Yamashita,T.; Nakanishi,O.
参考来源:J Med Chem 1999,42(15),3001
产品链接: CAS No. 209783-80-2›› 产品链接: CAS No.209784-80-5››