Asulacrine isethionate, Amsalog, NSC-343499, CI-921
9-(2-甲氧基-4-(甲基磺酰基氨基)苯胺基)-N,5-二甲基吖啶-4-甲酰胺 Chemical Name: 9-[2-Methoxy-4-(methylsulfonylamino)phenylamino]-N,5-dimethyl-4-acridinecarboxamide 2-hydroxyethanesulfonate
CAS No. 80841-48-1, 80841-47-0 (free base), 80841-46-9 (HCl)
项目整合开发状态: Phase I
项目研究机构: Cancer Research UK (Originator), Pfizer (Originator), Sparta (Licensee)
合成路线:2-Iodoisophthalic acid (II) is reacted with o-toluidine (I) to give 2-N-(2-methylphenyl)aminoisophthalic acid (III).Cyclization with concentrated H2SO4 provides the 5-methyl-9-oxoacridan-4-carboxylic acid (IV).Conversion of this compound to 5-methyl-9-chloroacridine-4-carbonyl chloride (V) and subsequent selective reaction first with methylamine to provide the methylcarboxamide (VI) and secondly with 4-amino-3-methoxymethanesulfonanilide (VII) gives the hydrochloride salt (VIII) of the desired compound.Conversion via the free base to the isethionate salt provides CI-921.
📌 参考资料/链接：
参考文献标题:CI-921
文献作者:Denny,W.A.; Atwell,G.J.; Baguley,B.C.
参考来源:Drugs Fut 1984,9(8),575
📄 详细内容
合成路线:2-Iodoisophthalic acid (II) is reacted with o-toluidine (I) to give 2-N-(2-methylphenyl)aminoisophthalic acid (III).Cyclization with concentrated H2SO4 provides the 5-methyl-9-oxoacridan-4-carboxylic acid (IV).Conversion of this compound to 5-methyl-9-chloroacridine-4-carbonyl chloride (V) and subsequent selective reaction first with methylamine to provide the methylcarboxamide (VI) and secondly with 4-amino-3-methoxymethanesulfonanilide (VII) gives the hydrochloride salt (VIII) of the desired compound.Conversion via the free base to the isethionate salt provides CI-921.
参考文献标题:Potential antitumor agents.40.Orally active 4,5-disubstituted derivatives of amsacrine
文献作者:Denny,W.A.; Atwell,G.J.; Baguley,B.C.
参考来源:J Med Chem 1984,27(3),363-366
合成路线:2-Iodoisophthalic acid (II) is reacted with o-toluidine (I) to give 2-N-(2-methylphenyl)aminoisophthalic acid (III).Cyclization with concentrated H2SO4 provides the 5-methyl-9-oxoacridan-4-carboxylic acid (IV).Conversion of this compound to 5-methyl-9-chloroacridine-4-carbonyl chloride (V) and subsequent selective reaction first with methylamine to provide the methylcarboxamide (VI) and secondly with 4-amino-3-methoxymethanesulfonanilide (VII) gives the hydrochloride salt (VIII) of the desired compound.Conversion via the free base to the isethionate salt provides CI-921.
参考文献标题:Synthesis and antitumour activity and DNA binding properties of a new derivative of amsacrine N,5-dimethyl-9-[(2-methoxy-4-methylsulfonylamino)phenylamino]-4-acridine carboxamide
文献作者:Baguley,B.C.; Denny,W.A.; Finlay,G.J.; Wilson,W.R.; Twigden,S.J.; Atwell,G.J.; Rewcastle,G.W.
参考来源:Cancer Res 1984,
产品链接: CAS No. 80841-48-1›› 产品链接: CAS No.80841-47-0››