2'-O-benzoyl-3'-N-debenzoyl-paclitaxel | 307923-51-9

• 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: 2'-O-benzoyl-3'-N-debenzoyl-paclitaxel
• 英文别名: isopaclitaxel；isotaxel；[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-amino-2-benzoyloxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 307923-51-9
• 化学式: C₄₇H₅₁NO₁₄
• 分子量: 853.92
• InChiKey: CKSHRCLXHASJJO-MZXODVADSA-N

物化性质

• 沸点：
  909.7±65.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  62
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  224
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2'-O-benzoyl-3'-N-debenzoyl-paclitaxel 在 邻氨基苯甲酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 以65%的产率得到紫杉醇
  参考文献：
  名称：

  [EN] CONVERSION OF TAXANE MOLECULES
  [FR] CONVERSION DE MOLÉCULES DE TAXANE

  摘要：

  该发明提供了还原性去氧化紫杉醇分子C-3'位置上的酰胺基团的方法和组合物，随后进行分子内酰基迁移，将酰基转移到C-3'位置。

  公开号：

  WO2003087079A1
• 作为产物：
  描述：

  3'-N-debenzoyl-3'-N-Troc-7-Troc-paclitaxel 在 4-二甲氨基吡啶 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2'-O-benzoyl-3'-N-debenzoyl-paclitaxel
  参考文献：
  名称：

  WO2023/77129

  摘要：

  公开号：

文献信息

• Method and compositions for preparing a compound using a benzoylating agent essentially free of ring chlorination
  申请人：Johnson H. James

  公开号：US20060035962A1

  公开（公告）日：2006-02-16

  This invention relates to methods and compositions for preparing compounds using a benzoylating agent essentially free of ring chlorination. In one alternative embodiment, the present invention relates to methods and compositions for preparing taxanes essentially free of ring chlorinated impurities. In another alternative embodiment, the present invention comprises methods of converting taxane amine with a benzoylating agent essentially free of ring chlorination.

  本发明涉及使用基本上不含环氯化物的苯甲酰化剂制备化合物的方法和组合物。在一种替代实施方案中，本发明涉及制备基本上不含环氯化杂质的紫杉醇的方法和组合物。在另一种替代实施方案中，本发明包括使用基本上不含环氯化物的苯甲酰化剂转化紫杉醇胺的方法。
• PRODRUGS CONTAINING NOVEL BIO-CLEAVABLE LINKERS
  申请人：SATYAM Apparao

  公开号：US20110274695A1

  公开（公告）日：2011-11-10

  The invention provides the compounds of formula (I) or pharmaceutically acceptable salts thereof. The invention also provides pharmaceutical compositions comprising one or more compounds of formula I or intermediates thereof and one more of pharmaceutically acceptable carriers, vehicles or diluents. The invention further provides methods of preparation and methods of use of prodrugs including NO-releasing prodrugs, double prodrugs and mutual prodrugs comprising the compounds of formula I.

  本发明提供公式(I)的化合物或其药学上可接受的盐。本发明还提供包括公式I的一个或多个化合物或其中间体以及一个或多个药学上可接受的载体、车载剂或稀释剂的制药组合物。本发明还提供制备方法和使用方法，包括包含公式I的NO释放前药、双重前药和相互前药的前药的使用方法。
• Development of novel water-soluble photocleavable protective group and its application for design of photoresponsive paclitaxel prodrugs
  作者：Mayo Noguchi、Mariusz Skwarczynski、Halan Prakash、Shun Hirota、Tooru Kimura、Yoshio Hayashi、Yoshiaki Kiso

  DOI：10.1016/j.bmc.2008.04.022

  日期：2008.5

  A novel coumarin-based highly water-soluble photocleavable protective group was designed and synthesized, and then this photosensitive protecting group was used to design paclitaxel prodrugs. These novel paclitaxel conjugates demonstrated excellent water solubility, over 100 mg mL(-1). Thus, the use of a detergent in the formulation can be omitted completely, even at high doses. Phototaxel 11 released the parent drug, paclitaxel, quickly and efficiently by minimal tissue-damaging 365 nm UV light irradiation at low power, while laser activation at 355 nm led to extensive decomposition of the prodrug. The carbamate-type prodrug, phototaxel 11, was stable in the dark prior to activation, whereas carbonate-type phototaxel 9 demonstrated poor stability under aqueous conditions. For such prodrugs, tumor-tissue targeting after administration could be achieved by selective light delivery, similar to that used in photodynamic therapy. In addition, newly designed coumarin derivative 8 can be applied in organic chemistry as a photosensitive protective group and for the design of caged compounds. (C) 2008 Elsevier Ltd. All rights reserved.
• A Novel Approach of Water-Soluble Paclitaxel Prodrug with No Auxiliary and No Byproduct:  Design and Synthesis of Isotaxel
  作者：Yoshio Hayashi、Mariusz Skwarczynski、Yoshio Hamada、Youhei Sohma、Tooru Kimura、Yoshiaki Kiso

  DOI：10.1021/jm034112n

  日期：2003.8.1

  A novel water-soluble paclitaxel prodrug, isotaxel 2, that realizes a higher water-solubility and the formation of paclitaxel through a simple pH-dependent chemical mechanism via the O-N acyl migration was synthesized and showed promising results in water-solubility and kinetics. This prodrug, a 2'-O-benzoyl isoform of paclitaxel, has no additional functional auxiliaries released during conversion to paclitaxel, which would be a great advantage in toxicology and medical economics.
• US8354455B2
  申请人：——

  公开号：US8354455B2

  公开（公告）日：2013-01-15