7-O-allyl-9(R)-dihydrotaxol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 7-O-allyl-9(R)-dihydrotaxol
• 英文别名: [(1S,2S,3R,4S,7R,9S,10R,11R,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,11-dihydroxy-10,14,17,17-tetramethyl-9-prop-2-enoxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• 化学式: C₅₀H₅₇NO₁₄
• 分子量: 896.001
• InChiKey: CDKYHXXAFVDNRM-JHRRHWCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  65
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  213
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  [(1S,2S,3R,4S,7R,9S,10R,11R,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-(1-ethoxyethoxy)-3-phenylpropanoyl]oxy-1,11-dihydroxy-10,14,17,17-tetramethyl-9-prop-2-enoxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate 在 盐酸 作用下， 以 乙醇 为溶剂， 以79%的产率得到7-O-allyl-9(R)-dihydrotaxol
  参考文献：
  名称：

  Antitumor Activity of 9(R)-Dihydrotaxane Analogs

  摘要：

  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.

  DOI：

  10.1021/jm00009a009

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.