Vesnarinone, OPC-8212, Arkin, Arkin-Z
维司力农Chemical Name: 1-(1,2,3,4-Tetrahydro-2-oxo-6-quinolyl)-4-veratroylpiperazine; 6-[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]-1,2,3,4-tetrahydro-2-quinolinone
CAS No. 81840-15-5
项目整合开发状态: Launched-1990
项目研究机构: Otsuka (Originator), Johns Hopkins University (Not Determined)
合成路线:OPC-8212 is obtained through the piperazine ring formation method from bis(beta-bromoethyl)amine hydrobromide and 6-amino-3,4-dihydro-2(1H)-quinolinone (V) to give (VI).(V) is synthesized using the ring closure reaction of p-acetylamino-beta-ethoxyacryloanilide (II).p-Acetylaminoaniline (I) is converted to (II) by treatment with beta-ethoxyacryloyl chloride and afterwards cyclized in the presence of sulfuric acid to give 6-acetylamino-2-(1H)-quinolinone (III).Hydrogenation of (III) over 10% palladium on charcoal gives 6-acetylamino-3,4-dihydro-2(1H)-quinolinone (IV).Hydrolysis of (IV) gives 6-amino-3,4-dihydro-2(1H)-quinolinone (V).OPC-8212 is obtained by adding 3,4-dimethoxybenzyl chloride (VII) to (VI).
📌 参考资料/链接：
参考文献标题:OPC-8212
文献作者:Mannhold,R.
参考来源:Drugs Fut 1985,10(1),28
📄 详细内容
合成路线:OPC-8212 is obtained through the piperazine ring formation method from bis(beta-bromoethyl)amine hydrobromide and 6-amino-3,4-dihydro-2(1H)-quinolinone (V) to give (VI).(V) is synthesized using the ring closure reaction of p-acetylamino-beta-ethoxyacryloanilide (II).p-Acetylaminoaniline (I) is converted to (II) by treatment with beta-ethoxyacryloyl chloride and afterwards cyclized in the presence of sulfuric acid to give 6-acetylamino-2-(1H)-quinolinone (III).Hydrogenation of (III) over 10% palladium on charcoal gives 6-acetylamino-3,4-dihydro-2(1H)-quinolinone (IV).Hydrolysis of (IV) gives 6-amino-3,4-dihydro-2(1H)-quinolinone (V).OPC-8212 is obtained by adding 3,4-dimethoxybenzyl chloride (VII) to (VI).
参考文献标题:Physicochemical properties and stabilities of a new positive inotropic agent,OPC 8212
文献作者:Nakagawa,K.; Osumi,T.; Shimizu,T.; Niimi,K.
参考来源:Arzneim-Forsch Drug Res 1984,34(3A),334-341
合成路线:OPC-8212 is obtained through the piperazine ring formation method from bis(beta-bromoethyl)amine hydrobromide and 6-amino-3,4-dihydro-2(1H)-quinolinone (V) to give (VI).(V) is synthesized using the ring closure reaction of p-acetylamino-beta-ethoxyacryloanilide (II).p-Acetylaminoaniline (I) is converted to (II) by treatment with beta-ethoxyacryloyl chloride and afterwards cyclized in the presence of sulfuric acid to give 6-acetylamino-2-(1H)-quinolinone (III).Hydrogenation of (III) over 10% palladium on charcoal gives 6-acetylamino-3,4-dihydro-2(1H)-quinolinone (IV).Hydrolysis of (IV) gives 6-amino-3,4-dihydro-2(1H)-quinolinone (V).OPC-8212 is obtained by adding 3,4-dimethoxybenzyl chloride (VII) to (VI).
参考文献标题:Studies on positive inotropic agents.I.Synthesis of 3,4-dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-quinolinone and related compounds
文献作者:Tominaga,M.; Yo,E.; Ogawa,H.; Yamashita,S.; Yabuuchi,Y.; Nakagawa,K.
参考来源:Chem Pharm Bull 1984,32(6),2100
产品链接: CAS No. 81840-15-5››