(2S,10S,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate | 1352212-95-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,10S,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate
• 英文别名: [(2S,10S,10aS)-2-[(2R,3S)-3-benzamido-2-hydroxy-3-(2-prop-2-enylphenyl)propanoyl]oxy-9-prop-2-enoxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-10-yl] benzoate
• CAS: 1352212-95-3
• 化学式: C₄₁H₄₀N₂O₇
• 分子量: 672.778
• InChiKey: UTFCQQAIHHBQRA-GXCFLFNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  间甲氧基苯甲醇 在 吡啶 、 sodium tetrahydroborate 、 Jones reagent 、 正丁基锂 、 氢氟酸 、 碘 、 三溴化硼 、 三乙酰氧基硼氢化钠 、 sodium hydride 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 14.68h， 生成 (2S,10S,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate
  参考文献：
  名称：

  Design and synthesis of simplified taxol analogs based on the T-Taxol bioactive conformation

  摘要：

  A series of compounds designed to adopt a conformation similar to the tubulin-binding T-Taxol conformation of the anticancer drug paclitaxel has been synthesized. Both the internally bridged analogs 37-39, 41 and the open- chain analogs 27-29 and 43 were prepared. The bridged analogs 37-39 and 41 were synthesized by Grubbs' metatheses of compounds 30-32 and 33, which, in turn, were prepared by coupling beta-lactams 24-26 with alcohols 22 and 23. Both the bridged and the open- chain analogs showed moderate to good cytotoxicity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.010

文献信息

• Design and synthesis of simplified taxol analogs based on the T-Taxol bioactive conformation
  作者：Jielu Zhao、Susan Bane、James P. Snyder、Haipeng Hu、Kamalika Mukherjee、Carla Slebodnick、David G.I. Kingston

  DOI：10.1016/j.bmc.2011.10.010

  日期：2011.12

  A series of compounds designed to adopt a conformation similar to the tubulin-binding T-Taxol conformation of the anticancer drug paclitaxel has been synthesized. Both the internally bridged analogs 37-39, 41 and the open- chain analogs 27-29 and 43 were prepared. The bridged analogs 37-39 and 41 were synthesized by Grubbs' metatheses of compounds 30-32 and 33, which, in turn, were prepared by coupling beta-lactams 24-26 with alcohols 22 and 23. Both the bridged and the open- chain analogs showed moderate to good cytotoxicity. (C) 2011 Elsevier Ltd. All rights reserved.