2α-benzoyloxy-5β,20-epoxy-4α-hydroxy-9α,10β-isopropylidenedioxy-11-taxen-13-one | 532935-93-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 2α-benzoyloxy-5β,20-epoxy-4α-hydroxy-9α,10β-isopropylidenedioxy-11-taxen-13-one
• 英文别名: [(2R,6R,7R,10R,13S,14R,15R,16R)-13-hydroxy-4,4,7,19,20,20-hexamethyl-18-oxo-3,5,11-trioxapentacyclo[14.3.1.02,6.07,14.010,13]icos-1(19)-en-15-yl] benzoate
• CAS: 532935-93-6
• 化学式: C₃₀H₃₈O₇
• 分子量: 510.628
• InChiKey: QNKFZXZMOIVICT-POTIHYLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  37.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2α-benzoyloxy-5β,20-epoxy-4α-hydroxy-9α,10β-isopropylidenedioxy-11-taxen-13-one 在 吡啶 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 53.0h， 生成 9α,10β-diacetoxy-2α-benzoyloxy-5β,20-epoxy-4α-hydroxy-11-taxen-13-one
  参考文献：
  名称：

  合成和2-抗肿瘤活性（米-取代的苯甲酰基）浆果赤霉素从taxinine III类似物

  摘要：

  由紫杉碱（日本紫杉叶的主要成分）制备2- m-叠氮基苯甲酰基和2- m-氯苯甲酰基浆果赤霉素III类似物。在这项研究中，观察到了新的从13-羟基迁移到4-羟基的乙酰基。评价了这些化合物的抗肿瘤活性。

  DOI：

  10.1016/s0040-4020(03)00048-6
• 作为产物：
  描述：

  (3aR,8R,9R,9aR,10S,11S,13aR,13bR)-10-hydroxy-10-(hydroxymethyl)-2,2,5,13a,14,14-hexamethyl-11-((methylsulfonyl)oxy)-6-oxo-3a,6,7,8,9,9a,10,11,12,13,13a,13b-dodecahydro-4,8-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-9-yl benzoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 以99%的产率得到2α-benzoyloxy-5β,20-epoxy-4α-hydroxy-9α,10β-isopropylidenedioxy-11-taxen-13-one
  参考文献：
  名称：

  Structure–activity relationships of some taxoids as multidrug resistance modulator

  摘要：

  1,7-Deoxy-4-deacetylbaccatin III (12) and its five analogues 6-9, 13, and their oxetane ring opened derivatives 14, 16, and 17, which were synthesized from taxinine, showed significant activity as MDR reversal agent by the assay of the calcein accumulation toward MDR human ovarian cancer 2780AD cells. The most effective compound 12 in this assay is actually efficient for the recovery of cytotoxic activity of paclitaxel (taxol), adriamycin (ADM), and vincristine (VCR) toward MDR 2780AD cells at the same level toward parental 2780 cells. This activity of 12 is very interesting because baccatin 111 (4) has no such MDR reversal activity but has cytotoxic activity. The essential functional groups inducing such a difference in biological activity between 4 and 12 are 4 alpha-acetoxyl for 4 and 4 alpha-hydroxyl for 12. In seven compounds possessing MDR reversal activity, compound 12 is the most desirable compound for anti-MDR cancer reversal agent, because it has the highest accumulation ability of anticancer agent in MDR cancer cells and weak cytotoxic activity. Compounds 8 and 13 showed significant cytotoxic activity toward HepG2 and VA-13, respectively, as well as MDR reversal activity. They are expected to become lead compounds for new types of anticancer agent or anti-MDR cancer agent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.068