camptothecin-20-O-crotonate | 194414-77-2

• 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-crotonate
• 英文别名: [(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] (E)-but-2-enoate
• CAS: 194414-77-2
• 化学式: C₂₄H₂₀N₂O₅
• 分子量: 416.433
• InChiKey: PBHQIQBKXUWKBF-MLENBVEFSA-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：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  85.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  间氯过氧苯甲酸 、 camptothecin-20-O-crotonate 以 苯 为溶剂， 反应 168.0h， 以72%的产率得到camptothecin-20-O-2',3'-epoxybutyrate
  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
• 作为产物：
  描述：

  trans-crotonic anhydride 、 喜树碱 在 吡啶 作用下， 反应 15.0h， 以31%的产率得到camptothecin-20-O-crotonate
  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

• Asymmetric Dihydroxylation onto the a,b-Unsaturated Carboxylic Ester Derivatives of Camptothecin
  作者：Keiko Tagami、Shuzo Takagi、Shigeki Sano、Motoo Shiro、Yoshimitsu Nagao

  DOI：10.3987/com-97-7892

  日期：——

  Dihydroxyalkanoic ester derivatives (4a,b) and (5a,b) of 20S-camptothecin (1) were diastereoselectively synthesized by exploiting osmium-catalyzed asymmetric dihydroxylation based on the Sharpless procedure. The absolute configuration of the newly formed chiral centers, the 2' and 3' positions of the 20-alkanoyl side chain of 4a,b and 5a,b was determined by the chemical correlation with the known chiral dihydroxyalkanoic acids.
• Camptothecin derivatives induce apoptosis and inhibit proliferation of prostate cancer PC-3M cells through downregulation of PI3K/Akt signaling pathway
  作者：Yan Zhao、Yijia Zheng、Xin Chen、Rui Du、Zhaowei Yan

  DOI：10.1016/j.phytol.2021.08.014

  日期：2021.12
• ESTROGEN CANCER THERAPY
  申请人：CELL THERAPEUTICS, INC.

  公开号：EP1957065A1

  公开（公告）日：2008-08-20
• PREDICTIVE MARKER FOR TOPOISOMERASE I INHIBITORS
  申请人：Bharti Ajit

  公开号：US20110027277A1

  公开（公告）日：2011-02-03

  The present invention generally relates to the fields of cancer therapy and cancer prevention. More particularly, the present invention generally relates to a diagnostic marker for predicting the efficacy of topoisomerase I (topo I) inhibitors in the treatment of cancers. More specifically, the present invention relates to methods, machines, computer systems, computable readable media and kits which can be used to identify and determine the effectiveness of topoisomerase I (topo I) inhibitors in the treatment of cancers, and in some embodiments, the level of sensitivity or resistance of a tumor cell to a topoisomerase I inhibitor, such as camptothecin (CPT), or CTP analogues such as topotecan and irinotecan and derivatives thereof. More specifically, the present invention related to methods, machines, computer systems, computable readable media and kits which can be used to determine the presence of phosphorylation of topoisomerase I polypeptide, in some embodiments phosphorylation at residue serine 10 (S10) of a topoisomerase I polypeptide, wherein the presence of phosphorylation, in particular the phosphorylation at serine 10 of a topoI polypeptide indicates a cancer is likely to be unresponsive to a topo I inhibitor, whereas the absence of phosphorylation, in particular, the absence of phosphorylation at residue serine 10 (S10) identifies a cancer is likely to be responsive to a topo I inhibitor. Other aspect of the present invention relate to phospho-serine 10 topoisomerase I antibodies and other protein binding moieties, and uses thereof.
• US8993309B2
  申请人：——

  公开号：US8993309B2

  公开（公告）日：2015-03-31