camptothecin-20-O-butyrate

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 喜树碱
• 英文名称: camptothecin-20-O-butyrate
• 英文别名: camptothecin-20-butyrate；[(19S)-19-ethyl-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl] butanoate
• 化学式: C₂₄H₂₂N₂O₅
• 分子量: 418.449
• InChiKey: ZXXDNLXRBIZIGE-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  85.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丁酸酐 、 喜树碱 以92%的产率得到camptothecin-20-O-butyrate
  参考文献：
  名称：

  Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs

  摘要：

  通用公式所代表的紫杉醇衍生物如下所述： 其中当R1为H时，R为C2-C4烷基、C6-C15烷基、C3-C8环烷基、C2-C15烯基或C2-C15环氧基；当R2为硝基或氨基时，R1为C1-C15烷基、C1-C15烯基、C3-C8环烷基或环氧基。还描述了包括这些特定紫杉醇衍生物的脂质体前药，其受限于脂质体传递系统。还公开了制备这些前药以及在癌症治疗中使用它们的方法。

  公开号：

  US06352996B1

文献信息

• Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs
  申请人：The Stehlin Foundation For Cancer Research

  公开号：US06352996B1

  公开（公告）日：2002-03-05

  Derivatives of camptothecin as represented by the general formula: are described, wherein when R1 is H, R. is a C2-C4 alkyl group, a C6-C15 alkyl group, a C3-C8 cycloalkyl group, a C2-C15 alkenyl group or a C2-C15 epoxy group; and when R2 is a nitro group or an amino group, R1 is a C1-C15 alkyl group, a C1-C15 alkenyl group, a C3-C8 cycloalkyl group, or an epoxy group. Liposomal prodrugs including these specific derivatives of camptothecin restrained by a liposomal delivery system are also described. Processes for making these prodrugs and for using them in cancer treatment are also disclosed.

  通用公式所代表的紫杉醇衍生物如下所述： 其中当R1为H时，R为C2-C4烷基、C6-C15烷基、C3-C8环烷基、C2-C15烯基或C2-C15环氧基；当R2为硝基或氨基时，R1为C1-C15烷基、C1-C15烯基、C3-C8环烷基或环氧基。还描述了包括这些特定紫杉醇衍生物的脂质体前药，其受限于脂质体传递系统。还公开了制备这些前药以及在癌症治疗中使用它们的方法。
• Camptothecin derivatives and improved synthetic methods
  申请人：Shull Keith Brian

  公开号：US20070099948A1

  公开（公告）日：2007-05-03

  The present invention relates to compositions and methods for preparing pharmaceutical compositions. In some embodiments, the invention includes compounds and methods of resolving chiral compounds. In some embodiments, the invention includes chiral and crystalline compositions and hydrates. In some embodiments, the invention contemplates compositions comprising camptothecin derivatives and synthetic intermediates thereof. In some embodiments, the invention includes methods of protecting, inserting, modifying, separating isomers, and removing chemical groups.

  本发明涉及制备药物组合物的组合物和方法。在某些实施例中，该发明包括化合物和解决手性化合物的方法。在某些实施例中，该发明包括手性和晶体组合物和水合物。在某些实施例中，该发明考虑包括紫杉醇衍生物及其合成中间体的组合物。在某些实施例中，该发明包括保护、插入、修改、分离异构体和去除化学基团的方法。
• US7517891B2
  申请人：——

  公开号：US7517891B2

  公开（公告）日：2009-04-14
• Alkyl Esters of Camptothecin and 9-Nitrocamptothecin:  Synthesis, in Vitro Pharmacokinetics, Toxicity, and Antitumor Activity
  作者：Zhisong Cao、Nick Harris、Anthony Kozielski、Dana Vardeman、John S. Stehlin、Beppino Giovanella

  DOI：10.1021/jm9607562

  日期：1998.1.1

  Eleven camptothecin esters, 6a-e and 7a-f, were prepared by straightforward acylation of camptothecins with the corresponding acylating reagents such as organic anhydrides and carboxylic acid chlorides. The in vitro pharmacokinetic determination of lactone levels of esters 6a and 7b showed that the biological life span of their lactone forms in human and mouse plasma significantly increased when compared with their mother compounds, camptothecin (3) and 9-nitrocamptothecin (4). The differences of lactone levels between human plasma and mouse plasma for 6a and 7b were much smaller than what was observed for their mother compounds. The in vivo antitumor activity and toxicity studies demonstrated that some of these esters were very active against human tumor xenografts in nude mice and had an exceptional lack of toxicity in nude mice, even at enormous doses.