NC-190, NCU-190Na
Chemical Name: N-[2-(Dimethylamino)ethyl]-9-carboxy-5-hydroxy-10-methoxybenzo[a]phenazine-6-carboxamide sodium salt; 6-[[2-(Dimethylamino)ethyl]carbamoyl]-5-hydroxy-10-methoxybenzo[a]phenazine-9-carboxylic acid sodium salt
项目整合开发状态: Phase II
项目研究机构: Taisho (Originator)
合成路线:NCU-190Na is synthesized by condensation of naphthoquinone (I) and phenylenediamine (II),but several isomers (IV) of benzo[a]phenazine are produced at the same time.Using ethyl chlorocarbonate,(III) is selectively produced and aminolysis of esters is also selective to the 6-position; thus,(V) is produced and can be converted to (VI) (NCU190Na).Various derivatives of (VI) can be synthesized in a similar manner.Compound (III) can also be prepared from naphthoquinone (I) and ethyl chloroformate (VII) to give ethyl 3-(ethoxycarbonyloxy)-1,4-dioxo-1,4-dihydro-2-naphthoate (VIII),which is condensed with phenylenediamine (II).
📌 参考资料/链接：
参考文献标题:Benzo[a]phenazine derivs.
文献作者:Migita,Y.; Eguchi,T.; Kumazawa,Y.; Nakagami,J.; Amano,T.; Sota,K.; Sakakibara,J.(Taisho Pharmaceutical Co.,Ltd.)
参考来源:EP 0196910; ES 8706651; JP 1987000072; US 4686292
📄 详细内容
合成路线:NCU-190Na is synthesized by condensation of naphthoquinone (I) and phenylenediamine (II),but several isomers (IV) of benzo[a]phenazine are produced at the same time.Using ethyl chlorocarbonate,(III) is selectively produced and aminolysis of esters is also selective to the 6-position; thus,(V) is produced and can be converted to (VI) (NCU190Na).Various derivatives of (VI) can be synthesized in a similar manner.Compound (III) can also be prepared from naphthoquinone (I) and ethyl chloroformate (VII) to give ethyl 3-(ethoxycarbonyloxy)-1,4-dioxo-1,4-dihydro-2-naphthoate (VIII),which is condensed with phenylenediamine (II).
参考文献标题:NCU-190Na
文献作者:Hoshi,A.
参考来源:Drugs Fut 1988,13(8),726
合成路线:NCU-190Na is synthesized by condensation of naphthoquinone (I) and phenylenediamine (II),but several isomers (IV) of benzo[a]phenazine are produced at the same time.Using ethyl chlorocarbonate,(III) is selectively produced and aminolysis of esters is also selective to the 6-position; thus,(V) is produced and can be converted to (VI) (NCU190Na).Various derivatives of (VI) can be synthesized in a similar manner.Compound (III) can also be prepared from naphthoquinone (I) and ethyl chloroformate (VII) to give ethyl 3-(ethoxycarbonyloxy)-1,4-dioxo-1,4-dihydro-2-naphthoate (VIII),which is condensed with phenylenediamine (II).
参考文献标题:Selective synthsesis of new benzo(a)-phenazine-6-c
文献作者:Watanabe,Y.; Soda,K.; Nakagami,J.; Sakakibara,Z.; Migita,Y.; Kumazawa,Y.
参考来源:108th Annu Meet Pharm Soc Jpn (April 4-7,Hiroshima) 1988,Abst 5E16 2-1
合成路线:NCU-190Na is synthesized by condensation of naphthoquinone (I) and phenylenediamine (II),but several isomers (IV) of benzo[a]phenazine are produced at the same time.Using ethyl chlorocarbonate,(III) is selectively produced and aminolysis of esters is also selective to the 6-position; thus,(V) is produced and can be converted to (VI) (NCU190Na).Various derivatives of (VI) can be synthesized in a similar manner.Compound (III) can also be prepared from naphthoquinone (I) and ethyl chloroformate (VII) to give ethyl 3-(ethoxycarbonyloxy)-1,4-dioxo-1,4-dihydro-2-naphthoate (VIII),which is condensed with phenylenediamine (II).
参考文献标题:Synthesis and antitumor activity of new benzo(a)-p
文献作者:Kumazawa,Y.; Nakagami,J.; Soda,K.; Nakaike,S.; Sakakibara,Z.; Watanabe,Y.; Migita,Y.
参考来源:108th Annu Meet Pharm Soc Jpn (April 4-7,Hiroshima) 1988,Abst 5E16 11-2