[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-(2,2,2-trichloroacetyl)oxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl] (4S,5R)-2,2-bis(chloromethyl)-4-phenyl-1,3-oxazolidine-5-carboxylate | 204125-01-9

• 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,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-(2,2,2-trichloroacetyl)oxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl] (4S,5R)-2,2-bis(chloromethyl)-4-phenyl-1,3-oxazolidine-5-carboxylate
• CAS: 204125-01-9
• 化学式: C₄₅H₄₈Cl₅NO₁₄
• 分子量: 1004.14
• InChiKey: ANAFNDHMFPZTCA-OXBSDYBMSA-N

物化性质

• 沸点：
  917.6±65.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  65
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  199
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-(2,2,2-trichloroacetyl)oxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl] (4S,5R)-2,2-bis(chloromethyl)-4-phenyl-1,3-oxazolidine-5-carboxylate 在 吡啶 、 乙酸铵 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 3'-N-cyclobutanecarbonyl-3'-N-debenzoylpaclitaxel
  参考文献：
  名称：

  Structure–activity relationship study at the 3′-N-position of paclitaxel: synthesis and biological evaluation of 3′-N-acyl-paclitaxel analogues

  摘要：

  A series of 3'-N-acyl-paclitaxel analogues la-v were synthesized and their cytotoxicities in vitro against several human tumor cell lines examined. It has been shown that distinct correlation between activity and N-acyl-substituent. The appropriate size of N-acyl group was indispensable for cytotoxicity, and moreover, the presence of beta-substituted conjugated double and triple bond to N-carbonyl generally resulted in increase of cytotoxicities. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00218-3
• 作为产物：
  描述：

  (4S,5R)-2,2-di(chloromethyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid triethylamine salt 、 7-trichloroacetylbaccatin III 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以84%的产率得到[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-(2,2,2-trichloroacetyl)oxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl] (4S,5R)-2,2-bis(chloromethyl)-4-phenyl-1,3-oxazolidine-5-carboxylate
  参考文献：
  名称：

  Synthesis and biology of 3′- N -acyl- N -debenzoylpaclitaxel analogues

  摘要：

  The, 3'-N-acyl-N-debenzoylpaclitaxel analogues 1a-d were synthesized and evaluated on biological systems. Some of the analogues 1a-d exhibited higher cytotoxicities (up to 20-fold) and stronger abilities to induce apoptosis than paclitaxel. In an in vivo experiment against i.p. implanted B16 melanoma, the most cytotoxic compound 1b in vitro caused tumor growth inhibition more than paclitaxel.

  DOI：

  10.1016/s0968-0896(99)00173-x

文献信息

• Radiolabeling of paclitaxel with electrophilic 123 I
  作者：Eun Joo Roh、Young Hoon Park、Choong Eui Song、Seung-Jun Oh、Yearn Seong Choe、Byung-Tae Kim、Dae Yoon Chi、Deukjoon Kim

  DOI：10.1016/s0968-0896(99)00255-2

  日期：2000.1

  I-123-Labeled paclitaxel, [I-123]-1 was prepared by electrophilic aromatic radioiodination of 3'-N-(p-trimethylstannyl-benzoyl)-3'-debenzoylpaclitaxel I-123(-) in the presence of peracetic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Roh; Park; Oh, Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S285-S287
  作者：Roh、Park、Oh、Song、Oh、Choe、Kim、Chi、Kim

  DOI：——

  日期：——