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【结 构 式】 
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【药物名称】Laromustine, VNP-40101M, 101M, Cloretazine 【化学名称】1-(2-Chloroethyl)-4-methyl-1,2-bis(methylsulfonyl)semicarbazide 【CA登记号】173424-77-6 【 分 子 式 】C6H14ClN3O5S2 【 分 子 量 】307.77658 |
【开发单位】Yale University (Originator), Vion (Licensee) 【药理作用】Chemical Delivery Systems, DRUG DELIVERY, Drug Delivery Systems, Leukemia Therapy, Myelodysplastic Syndrome Therapy, Myeloid Leukemia Therapy, Oncolytic Drugs, Solid Tumors Therapy, Antimitotic Drugs, DNA Alkylating Drugs |
合成路线1
The reaction of (2-hydroxyethyl)hydrazine (I) with MsCl in pyridine gives the trimesylated compound (II), which is treated with LiCl in refluxing acetone to yield 1-(2-chloroethyl)-1,2-bis(methanesulfonyl)hydrazine (III) (1). Finally, this compound is condensed with methyl isocyanate (IV) by means of TEA in acetonitrile to afford the target semicarbazide.
| 【1】 Shyam, K.; et al.; Antitumor 2-(aminocarbonyl)-1,2-bis(methylsulfonyl)-1-(2-chloroethyl)hydrazines. J Med Chem 1996, 39, 3, 796. |
| 【2】 Satorelli, A.C.; Shyam, K.; Penketh, P.G. (Yale University); Antitumor 2-aminocarbonyl-1,2-bis(methylsulfonyl)-1-(substd.)hydrazines. EP 0841912; JP 1999508898; WO 9702029 . |
| 【3】 Shyam, K.; et al.; Synthesis and evaluation of 1,2, 2-tris(sulfonyl)hydrazines as antineoplastic and trypanocidal agents. J Med Chem 1990, 33, 8, 2259. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 24951 | 2-hydrazino-1-ethanol | 109-84-2 | C2H8N2O | 详情 | 详情 |
| (II) | 48610 | 2-[1,2-bis(methylsulfonyl)hydrazino]ethyl methanesulfonate | C5H14N2O7S3 | 详情 | 详情 | |
| (III) | 48611 | N-(2-chloroethyl)-N'-(methylsulfonyl)methanesulfonohydrazide | C4H11ClN2O4S2 | 详情 | 详情 | |
| (IV) | 11019 | (Methylimino)(oxo)methane; methyl isocyanate | C2H3NO | 详情 | 详情 |