9(R)-dihydrotaxol 7,9-acetonide | 148584-54-7

• 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: 9(R)-dihydrotaxol 7,9-acetonide
• 英文别名: [(1R,2S,5R,7S,11R,12R,15S,17S,18S,19S)-2,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-17-hydroxy-9,9,14,19,20,20-hexamethyl-4,8,10-trioxapentacyclo[9.7.1.113,17.02,5.07,19]icos-13-en-18-yl] benzoate
• CAS: 148584-54-7
• 化学式: C₅₀H₅₇NO₁₄
• 分子量: 896.001
• InChiKey: TZMQGDKKBMOIEN-PVLZIVLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  65
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  202
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  9(R)-dihydrotaxol 7,9-acetonide 在 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 以56%的产率得到9-二氢紫杉醇
  参考文献：
  名称：

  Synthesis of 9-dihydrotaxol: A novel bioactive taxane

  摘要：

  The synthesis of 9-dihydrotaxol (8) is described via a novel deacylation reaction. This analog exhibits increased activity in the microtubule assay.

  DOI：

  10.1016/s0040-4039(00)60342-8
• 作为产物：
  描述：

  7,9-acetonide 13-acetyl-9-dihydrobaccatin III 在 盐酸 、 正丁基锂 作用下， 生成 9(R)-dihydrotaxol 7,9-acetonide
  参考文献：
  名称：

  Synthesis of 9-dihydrotaxol: A novel bioactive taxane

  摘要：

  The synthesis of 9-dihydrotaxol (8) is described via a novel deacylation reaction. This analog exhibits increased activity in the microtubule assay.

  DOI：

  10.1016/s0040-4039(00)60342-8

文献信息

• Antitumor Activity of 9(R)-Dihydrotaxane Analogs
  作者：Larry L. Klein、Leping Li、Clarence J. Maring、Clinton M. Yeung、Sheela A. Thomas、David J. Grampovnik、Jacob J. Plattner

  DOI：10.1021/jm00009a009

  日期：1995.4

  A novel reduced taxane, 13-acetyl-9(R)-dihydrobaccatin III (1) has been isolated from Taxus canadensis. The selective C-13 deacetylation of this isolate has allowed for the preparation of a wide variety of 9(R)-dihydrotaxane analogs. In general, this series has shown greater stability and water solubility than the 9-carbonyl series while retaining antimicrotubule and tumor cell cytotoxicity activities relative to taxol. Placement of polar functionalities at the C-7 position results in loss of activity whereas alkylation or acylation of either C-7 or C-9 hydroxyl groups ameliorate the activity.
• Water-soluble compound
  申请人：Tuszynski A. Jack

  公开号：US20070027129A1

  公开（公告）日：2007-02-01

  A water-soluble magnetic anti-mitotic compound with a water-solubility of at least 100 micrograms per milliliter, a molecular weight of at least 150 grams per mole, a mitotic index factor of at least 10 percent, a positive magnetic susceptibility of at least 1,000×10 −6 cgs, and a magnetic moment of at least 0.5 bohr magnetrons, wherein said compound is comprised of at least 7 carbon atoms and at least one inorganic atom with a positive magnetic susceptibility of at least 200×10 −6 cgs.
• Process for treating a biological organism
  申请人：Tuszynski Jack

  公开号：US20080119421A1

  公开（公告）日：2008-05-22

  A process for treating a biological organism, comprising the steps in which a cell cycle arresting drug is administered to the organism to produce synchronized cells, the microtubules within the synchronized cells are stabilized by means of a microtubule stabilizing agent, and the synchronized cells with the stabilized microtubules are then contacted with mechanical vibrational energy.
• Synthesis of 9-dihydrotaxol: A novel bioactive taxane
  作者：Larry L. Klein

  DOI：10.1016/s0040-4039(00)60342-8

  日期：1993.3

  The synthesis of 9-dihydrotaxol (8) is described via a novel deacylation reaction. This analog exhibits increased activity in the microtubule assay.