溴匹立明
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臨床資料 | |
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識別資訊 | |
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CAS號 | 56741-95-8 |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.231.001 |
化學資訊 | |
化學式 | C10H8BrN3O |
摩爾質量 | 266.10 g·mol−1 |
3D模型(JSmol) | |
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溴匹立明(INN:Bropirimine)是一種具有抗癌和抗病毒特性的實驗藥物。它是一種有效的口服免疫調節劑,正在嘗試治療膀胱癌。[1]
合成
![](http://images.weserv.nl/?url=//upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Bropirimine_synthesis.png/700px-Bropirimine_synthesis.png)
第一步,通過使用丁基鋰處理形成丙二酸半酯的二價陰離子。使用苯甲醯氯對該陰離子進行醯化反應,反應會在更具親核性的碳負離子上進行(因為具有較高的電荷密度)。這種三羰基化合物在酸化時脫羧生成β-酮酯。與胍縮合生成嘧啶酮。NBS 介導的溴化反應可生成溴匹立明。
參考資料
- ^ Akaza H, Kotake T, Machida T. Bropirimine, an orally active anticancer agent for superficial bladder cancer. European Urology. August 1998, 34 (2): 107–10. PMID 9693244. S2CID 46069874. doi:10.1159/000019693.
- ^ Skulnick HI, Weed SD, Eidson EE, Renis HE, Wierenga W, Stringfellow DA. Pyrimidinones. 1. 2-Amino-5-halo-6-aryl-4(3H)-pyrimidinones. Interferon-inducing antiviral agents. Journal of Medicinal Chemistry. December 1985, 28 (12): 1864–9. PMID 2999405. doi:10.1021/jm00150a018.
- ^ Brown TB, Stevens MF. Triazines and related products. Part XV. 2,4-Diaminopyrimidines and 2-aminopyrimidin-4(3H)-ones bearing 1,2,3-benzotriazinyl groups as potential dihydrofolic reductase inhibitors. Journal of the Chemical Society, Perkin Transactions 1. 1975, (11): 1023–8. PMID 1170192. doi:10.1039/p19750001023.
- ^ Stevens MF, Baig GU, Gate EN, Wheelhouse RT. Structural studies on bioactive compounds. Part 27. Chemistry of the immunomodulatory agent bropirimine. Anti-Cancer Drug Design. April 1995, 10 (3): 215–26. PMID 7748456.