新产品编号:427649
Chemical Name: N,N'-[1,3-Propanediylbis[(methylimino)-2,1-ethanediyl]]bis[4-methyl-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxamide]
CAS No. 214637-59-9
项目整合开发状态: Preclinical
项目研究机构: La Trobe University (Originator), University of Auckland (Originator)
合成路线:Methyl anthranilate (I) was condensed with chloral hydrate and hydroxylamine to produce the hydroxymino acetamide (II),which was cyclized to the required isatin-7-carboxylic acid (III) in hot concentrated sulfuric acid.The Pfitzinger condensation of isatin (III) with 7-methyl-1-indanone (IV) gave rise to indenoquinoline (V).Ketone (VI) was then obtained by oxidation of (V) with potassium permanganate in the presence of sodium carbonate.Subsequent thermal decarboxylation of diacid (VI) afforded monocarboxylic acid (VII) (1).After activation of acid (VII) as the corresponding imidazolide (VIII) upon treatment with N,N'-carbonyl diimidazole,coupling with tetraamine (IX) furnished the title bisamide.
📌 参考资料/链接：
参考文献标题:Topoisomerase inhibitors
文献作者:Denny,W.A.; Deady,L.W.; Kaye,A.J.(La Trobe University)
参考来源:WO 9845272
📄 详细内容
合成路线:Methyl anthranilate (I) was condensed with chloral hydrate and hydroxylamine to produce the hydroxymino acetamide (II),which was cyclized to the required isatin-7-carboxylic acid (III) in hot concentrated sulfuric acid.The Pfitzinger condensation of isatin (III) with 7-methyl-1-indanone (IV) gave rise to indenoquinoline (V).Ketone (VI) was then obtained by oxidation of (V) with potassium permanganate in the presence of sodium carbonate.Subsequent thermal decarboxylation of diacid (VI) afforded monocarboxylic acid (VII) (1).After activation of acid (VII) as the corresponding imidazolide (VIII) upon treatment with N,N'-carbonyl diimidazole,coupling with tetraamine (IX) furnished the title bisamide.
参考文献标题:Synthesis and antitumor activity of some indeno[1,2-b]quinoline-based bis carboxamides
文献作者:Deady,L.W.; Desneves,J.; Kaye,A.J.; Finlay,G.J.; Baguley,B.C.; Denny,W.A.
参考来源:Bioorg Med Chem 2000,8(5),977