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【结 构 式】 
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【药物名称】Darinaparsin, DMS(III)G，SGLU1，ZIO-101，Zinapar 【化学名称】L-γ-Glutamyl-S-(dimethylarsino)-L-cysteinyl-glycine，S-(Dimethylarsino)glutathione 【CA登记号】69819-86-9 【 分 子 式 】C12H22AsN3O6S 【 分 子 量 】411.306 |
【开发单位】Ziopharm Oncology (US). 【药理作用】Organic Arsenical，Apoptosis Inducer，Oncolytic |
合成路线1
Darinaparsin can be obtained by reaction of glutathione (I) under nitrogen atmosphere with either dimethylchloroarsine (II) in the presence of pyridine in dimethoxyethane (1, 2) or water/ethanol (3), or with dimethylarsinic acid (III) in water (4). Scheme 1.
| 【1】 Zingaro, R.A., Freireich, E.L., Sotelo-Lerma, M., Kantarjian, H., Verstovsek, S., Dukale, H. (University of Texas System; Texas A&M University). S-Dimethylarsino-thiosuccinic acid S-dimethylarsino-2-thiobenzoic acid S-(dimethylarsino)glutathione as treatments for cancer. CA 2472633, EP 1474128, JP 2005527487, US 2004034095, US 6911471, WO 2003057012. |
| 【2】 Zingaro, R.A., Duzkale, H., Freireich, E.J., Kantarjian, H., Sotelo-Lerma, M., Verstovsek, S., Gao, M. (Texas A&M University; University of Texas System). Compounds and methods for treatment of cancer. EP 1771459, JP 2008506710, WO 2006020048. |
| 【3】 Gutsch, P., Renzelmann, B. (Ziopharm Oncology, Inc.). Compounds and methods for the treatment of cancer. CA 2617049, EP 1919564, JP 2009502971, US 2007183972, WO 2007027344. |
| 【4】 Cullen, W.R., McBride, B.C., Reglinski, J. The reaction of methylarsenicals with thiols: Some biological implications. J Inorg Biochem 1984, 21(3): 179-94. |
| 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) | 29436 | (2S)-2-amino-5-[[(1R)-2-[(carboxymethyl)amino]-2-oxo-1-(sulfanylmethyl)ethyl]amino]-5-oxopentanoic acid | 70-18-8 | C10H17N3O6S | 详情 | 详情 |
| (II) | 65826 | Chlorodimethylarsine; Chloro-Dimethyl-Arsane | 557-89-1 | C2H6AsCl | 详情 | 详情 |
| (III) | 65827 | Cacodylic acid; Dimethylarsinic acid | 75-60-5 | C2H7AsO2 | 详情 | 详情 |
Extended Information