SW-33377, SR-233377, Win-33377, -Drug Synthesis Database

【结构式】

【药物名称】SW-33377, SR-233377, Win-33377

【化学名称】N-[1-[2-(Diethylamino)ethylamino]-9-oxothioxanthen-4-ylmethyl]methanesulfonamide
　　　　　　1-[2-(Diethylamino)ethylamino]-4-(methanesulfonamidomethyl)thioxanthen-9-one

【CA登记号】146537-07-7

【分子式】C₂₁H₂₇N₃O₃S₂

【分子量】433.59564

【开发单位】Sanofi-synthélabo (Originator)

【药理作用】Oncolytic Drugs

合成路线1

Leuckart reaction of aldehyde (I) with formamide/formic acid at 160 C provided formamide derivative (II), which was hydrolyzed with refluxing 2N HCl to afford benzylic amine (III). Finally, treatment with methanesulfonyl chloride, in the presence of NEt3 yielded the title sulfonamide.

参考文献中间体

【1】 Perni, R.B.; Wentland, M.P.; Huang, J.I.; Powles, R.G.; Aldous, S.; Klingbeil, K.M.; Peverly, A.D.; Robinson, R.G.; Corbett, T.H.; Jones, J.L.; Mattes, K.C.; Rake, J.B.; Coughlin, S.A.; Synthesis and antitumor activity of 4-aminomethylthioxanthenone and 5-aminomethylbenzothiopyranoindazole derivatives. J Med Chem 1998, 41, 19, 3645.
【2】 Wentland, M.P.; et al.; Anti-solid tumor efficacy and preparation of N-[[1-[[2-(diethylamino)ethyl]amino]-9-oxo-9H-thioxanthen-4-yl]methyl]methanesulfonamide (WIN 33377) and related derivatives. Bioorg Med Chem Lett 1994, 4, 4, 609.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	27504	1-[[2-(diethylamino)ethyl]amino]-9-oxo-9H-thioxanthene-4-carbaldehyde	C₂₀H₂₂N₂O₂S	详情	详情
(II)	27505	(1-[[2-(diethylamino)ethyl]amino]-9-oxo-9H-thioxanthen-4-yl)methylformamide	C₂₁H₂₅N₃O₂S	详情	详情
(III)	27506	4-(aminomethyl)-1-[[2-(diethylamino)ethyl]amino]-9H-thioxanthen-9-one	C₂₀H₂₅N₃OS	详情	详情

Extended Information