新产品编号:1077851
Chemical Name: 5-[4-[2-[1-(6-Phenyl-3-pyridyl)ethylideneaminooxy]ethoxy]benzyl]thiazolidine-2,4-dione
项目整合开发状态: Biological Testing
项目研究机构: Sankyo (Originator)
合成路线:This compound has been obtained by two related ways:1) The condensation of 4-acetylbiphenyl oxime (I) with 2-(2-bromoethoxy)tetrahydropyran (II) by means of K2CO3 in hot dimethylacetamide gives the oxime derivative (III),which is treated with TsOH in methanol yielding 4-acetylbiphenyl O-(2-hydroxyethyl)oxime (IV).The condensation of (IV) with 5-(4-hydroxybenzyl)-3-tritylthiazolidine-2,4-dione (V) by means of diethyl azodicarboxylate (DEAD) and PPh3 in THF affords (VI),the trityl derivative of the target compound,which is finally treated with hot aqueous ethanol to eliminate the trityl group.2) The condensation of 5-(4-hydroxybenzyl)thiazolidine-2,4-dione (VIII) with N-(2-hydroxyethoxy)phthalimide (VII) by means DEAD gives the adduct (IX),which is treated with hydrazine to eliminate the phthalimido group yielding the substituted hydroxylamine (X).Finally,this compound is condensed with 4-acetylbiphenyl (XI) by means of TEA.
合成路线:This compound has been obtained by two related ways:1) The condensation of 3-acetyl-6-phenylpyridine oxime (I) with 2-(2-bromoethoxy)tetrahydropyran (II) by means of K2CO3 in hot dimethylacetamide gives the oxime derivative (III),which is treated with TsOH in methanol yielding 3-acetyl-6-phenylpyridine O-(2-hydroxyethyl)oxime (IV).The condensation of (IV) with 5-(4-hydroxybenzyl)-3-tritylthiazolidine-2,4-dione (V) by means of diethyl azodicarboxylate (DEAD) and PPh3 in THF affords (VI),the trityl derivative of the target compound,which is finally treated with hot aqueous ethanol to eliminate the trityl group.2) The condensation of 5-(4-hydroxybenzyl)thiazolidine-2,4-dione (VIII) with N-(2-hydroxyethoxy)phthalimide (VII) by means DEAD gives the adduct (IX),which is treated with hydrazine to eliminate the phthalimido group yielding the substituted hydroxylamine (X).Finally,this compound is condensed with 3-acetyl-6-phenylpyridine (XI) by means of TEA.
📌 参考资料/链接：
参考文献标题:Oxime derivs.,their preparation and their therapeutic use
文献作者:Yanagisawa,H.; Fujita,T.; Fujimoto,K.; Yoshioka,T.; Wada,K.; Oguchi,M.; Fujiwara,T.; Horikoshi,H.(Sankyo Co.,Ltd.)
参考来源:CA 2159938; EP 0708098; JP 1997048779; US 5703096; US 5780490; US 5972959
📄 详细内容
合成路线:This compound has been obtained by two related ways:1) The condensation of 4-acetylbiphenyl oxime (I) with 2-(2-bromoethoxy)tetrahydropyran (II) by means of K2CO3 in hot dimethylacetamide gives the oxime derivative (III),which is treated with TsOH in methanol yielding 4-acetylbiphenyl O-(2-hydroxyethyl)oxime (IV).The condensation of (IV) with 5-(4-hydroxybenzyl)-3-tritylthiazolidine-2,4-dione (V) by means of diethyl azodicarboxylate (DEAD) and PPh3 in THF affords (VI),the trityl derivative of the target compound,which is finally treated with hot aqueous ethanol to eliminate the trityl group.2) The condensation of 5-(4-hydroxybenzyl)thiazolidine-2,4-dione (VIII) with N-(2-hydroxyethoxy)phthalimide (VII) by means DEAD gives the adduct (IX),which is treated with hydrazine to eliminate the phthalimido group yielding the substituted hydroxylamine (X).Finally,this compound is condensed with 4-acetylbiphenyl (XI) by means of TEA.
合成路线:This compound has been obtained by two related ways:1) The condensation of 3-acetyl-6-phenylpyridine oxime (I) with 2-(2-bromoethoxy)tetrahydropyran (II) by means of K2CO3 in hot dimethylacetamide gives the oxime derivative (III),which is treated with TsOH in methanol yielding 3-acetyl-6-phenylpyridine O-(2-hydroxyethyl)oxime (IV).The condensation of (IV) with 5-(4-hydroxybenzyl)-3-tritylthiazolidine-2,4-dione (V) by means of diethyl azodicarboxylate (DEAD) and PPh3 in THF affords (VI),the trityl derivative of the target compound,which is finally treated with hot aqueous ethanol to eliminate the trityl group.2) The condensation of 5-(4-hydroxybenzyl)thiazolidine-2,4-dione (VIII) with N-(2-hydroxyethoxy)phthalimide (VII) by means DEAD gives the adduct (IX),which is treated with hydrazine to eliminate the phthalimido group yielding the substituted hydroxylamine (X).Finally,this compound is condensed with 3-acetyl-6-phenylpyridine (XI) by means of TEA.
参考文献标题:Novel oximes having 5-benzyl-2,4-thiazolidinedione as antihyperglycemic agents: Synthesis and structure-activity relationship
文献作者:Yanagisawa,H.; Takamura,M.; Yamada,E.; Fujita,S.; Fujiwara,T.; Yachi,M.; Isobe,A.; Hagisawa,Y.
参考来源:Bioorg Med Chem Lett 2000,10(4),373