溴匹立明
临床资料 | |
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识别信息 | |
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CAS号 | 56741-95-8 |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.231.001 |
化学信息 | |
化学式 | C10H8BrN3O |
摩尔质量 | 266.10 g·mol−1 |
3D模型(JSmol) | |
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溴匹立明(INN:Bropirimine)是一种具有抗癌和抗病毒特性的实验药物。它是一种有效的口服免疫调节剂,正在尝试治疗膀胱癌。[1]
合成
第一步,通过使用丁基锂处理形成丙二酸半酯的二价阴离子。使用苯甲酰氯对该阴离子进行酰化反应,反应会在更具亲核性的碳负离子上进行(因为具有较高的电荷密度)。这种三羰基化合物在酸化时脱羧生成β-酮酯。与胍缩合生成嘧啶酮。NBS 介导的溴化反应可生成溴匹立明。
参考资料
- ^ 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.