Ro-09-3024, -Drug Synthesis Database

【结构式】

【药物名称】Ro-09-3024

【化学名称】5-[N-(6,6-Dimethyl-2,4-heptadiynyl)-N-methylamino]-1,2,3,4-tetrahydroquinolin-2-one

【CA登记号】

【分子式】C₁₉H₂₂N₂O

【分子量】294.39999

【开发单位】Chugai (Originator)

【药理作用】Antifungal Agents, ANTIINFECTIVE THERAPY

合成路线1

The Wittig reaction of 2,6-dinitrobenzaldehyde (I) with (ethoxycarbonylmethylene)triphenylphosphorane (A) produced methyl 2,6-dinitrocinnamate (II). Hydrogenation of the nitro groups and the olefinic double bond of (II) with concomitant cyclization furnished the tetrahydroquinolinone (III). Reductive alkylation of (III) with 6,6-dimethylheptadiynal (IV) and sodium cyanoborohydride produced the secondary amine (V). Finally, the N-methyl group was introduced by a second reductive alkylation with formaldehyde.

参考文献中间体

【1】 Masabuchi, K.; Umeda, I.; Taniguchi, M.; et al.; Synthesis and structure-activity relationships of novel fungal chitin synthase inhibitors. Bioorg Med Chem Lett 2000, 10, 13, 1459.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	14689	Methyl (triphenylphosphoranylidene)acetate; (methoxycarbonylmethylene)triphenylphosphorane；Methyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate	2605-67-6	C₂₁H₁₉O₂P	详情	详情
(I)	39891	2,6-dinitrobenzaldehyde	606-31-5	C₇H₄N₂O₅	详情	详情
(II)	44995	methyl (E)-3-(2,6-dinitrophenyl)-2-propenoate		C₁₀H₈N₂O₆	详情	详情
(III)	44996	5-amino-3,4-dihydro-2(1H)-quinolinone		C₉H₁₀N₂O	详情	详情
(IV)	44997	6,6-dimethyl-2,4-heptadiynal		C₉H₁₀O	详情	详情
(V)	44998	5-[(6,6-dimethyl-2,4-heptadiynyl)amino]-3,4-dihydro-2(1H)-quinolinone		C₁₈H₂₀N₂O	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)