[(1S,2S,3R,4S,7R,9S,10S,12S,15S)-4-acetyloxy-15-[(2R,3S)-3-(hexanoylamino)-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-12-propanoyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate | 876717-26-9

• 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: [(1S,2S,3R,4S,7R,9S,10S,12S,15S)-4-acetyloxy-15-[(2R,3S)-3-(hexanoylamino)-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-12-propanoyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 876717-26-9
• 化学式: C₄₇H₅₉NO₁₄
• 分子量: 861.984
• InChiKey: JRBDBPVHBPOEGY-PMCUCSHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  62
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  221
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  紫杉醇 C 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 戴斯-马丁氧化剂 、 氟化氢吡啶 、 一水合肼 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 、 二乙二醇二甲醚 为溶剂， 反应 2.0h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12S,15S)-4-acetyloxy-15-[(2R,3S)-3-(hexanoylamino)-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-12-propanoyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Single-site chemical modification at C10 of the baccatin III core of paclitaxel and Taxol C reduces P-glycoprotein interactions in bovine brain microvessel endothelial cells

  摘要：

  A single-site modification of paclitaxel analogs at the C10 position on the baccatin III core that reduces interaction with P-glycoprotein in bovine brain microvessel endothelial cells is described. Modification and derivatization of the C10 po\sition were carried out using a substrate controlled hydride addition to a key C9 and C10 diketone intermediate. The analogs were tested for tubulin assembly and cytotoxicity, and were shown to retain potency similar to paclitaxel. P-glycoprotein interaction was examined using a rhodamine assay and it was found that simple hydrolysis or epimerization of the C10 acetate of paclitaxel and Taxol C can reduce interaction with the P-glycoprotein transporter that may allow for increased permeation of taxanes into the brain. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.063

文献信息

• Single-site chemical modification at C10 of the baccatin III core of paclitaxel and Taxol C reduces P-glycoprotein interactions in bovine brain microvessel endothelial cells
  作者：Jared T. Spletstoser、Brandon J. Turunen、Kelly Desino、Antonie Rice、Apurba Datta、Dinah Dutta、Jacquelyn K. Huff、Richard H. Himes、Kenneth L. Audus、Anna Seelig、Gunda I. Georg

  DOI：10.1016/j.bmcl.2005.10.063

  日期：2006.2

  A single-site modification of paclitaxel analogs at the C10 position on the baccatin III core that reduces interaction with P-glycoprotein in bovine brain microvessel endothelial cells is described. Modification and derivatization of the C10 po\sition were carried out using a substrate controlled hydride addition to a key C9 and C10 diketone intermediate. The analogs were tested for tubulin assembly and cytotoxicity, and were shown to retain potency similar to paclitaxel. P-glycoprotein interaction was examined using a rhodamine assay and it was found that simple hydrolysis or epimerization of the C10 acetate of paclitaxel and Taxol C can reduce interaction with the P-glycoprotein transporter that may allow for increased permeation of taxanes into the brain. (c) 2005 Elsevier Ltd. All rights reserved.