Toborinone, OPC-18790, Tobonone
托波力农Chemical Name: (?-6-[3-(3,4-Dimethoxybenzylamino)-2-hydroxypropoxy]carbostyril; (?-6-[3-(3,4-Dimethoxybenzylamino)-2-hydroxypropoxy]-1,2-dihydroquinolin-2-one
CAS No. 143343-83-3, 128668-62-2 ((R)-isomer), 128668-65-5 ((S)-isomer), 128667-95-8 (undefined isomer)
项目整合开发状态: Discontinued
项目研究机构: Otsuka (Originator)
合成路线:6-Hydroxy-2(1H)-quinolinone (I) is alkylated with epichlorohydrin in the presence of K2CO3 in MeOH to afford 6-(2,3-epoxypropoxy)-2(1H)-quinolinone (II).Ring opening of the epoxide (II) with 3,4-dimethoxybenzylamine gives OPC-18790.This compound is also obtained by the reductive alkylation of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone (III) with 3,4-dimethoxybenzaldehyde.
📌 参考资料/链接：
参考文献标题:Novel positive inotropic agents; synthesis and biological activities of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone derivatives
文献作者:Fujioka,T.; Teramoto,S.; Mori,T.; Hosokawa,T.; Sumida,T.; Tominaga,M.; Yabuuchi,Y.
参考来源:J Med Chem 1992,35(20),3607-12
📄 详细内容
合成路线:6-Hydroxy-2(1H)-quinolinone (I) is alkylated with epichlorohydrin in the presence of K2CO3 in MeOH to afford 6-(2,3-epoxypropoxy)-2(1H)-quinolinone (II).Ring opening of the epoxide (II) with 3,4-dimethoxybenzylamine gives OPC-18790.This compound is also obtained by the reductive alkylation of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone (III) with 3,4-dimethoxybenzaldehyde.
参考文献标题:OPC-18790
文献作者:Fujioka,T.
参考来源:Drugs Fut 1993,18(12),1114
合成路线:The synthesis of the (+)-(R)-isomer of OPC-18790 has been published:The condensation of 6-hydroxyquinolin-2(1H)-one (I) with (S)-(+)-epichlorohydrin (II) by means of triethylamine in methanol gives (S)-(+)-6-(3-chloro-2-hydroxypropoxy)quinolin-2(1H)-one (III),which by reaction with KOH in isopropanol/water yields the (R)-(-)-epoxide (IV).Finally,this compound is condensed with 3,4-dimethoxybenzylamine (V) by heating its mixture at 80 C.The (+)-(R)-isomer is about 10-fold more potent than the (-)-(S)-isomer.
参考文献标题:Synthesis and biological activities of optically active 6-[3-(3,4-dimethox ybenzylamino)-2 hydroxypropoxy]-2(1H)-quinolinone (OPC-18790)
文献作者:Fujioka,T.; Teramoto,S.; Tsujimi,S.; Takemoto,K.; Mori,T.; Hosokawa,T.; Sumida,T.; Tominaga,M.; Yabuuchi,Y.
参考来源:Chem Pharm Bull 1996,44(8),1596
产品链接: CAS No. 143343-83-3››