2-(2-Allyloxycarbonyl-ethyl)-benzoic acid | 187840-93-3

• 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: 2-(2-Allyloxycarbonyl-ethyl)-benzoic acid
• 英文别名: 2-(3-Oxo-3-prop-2-enoxypropyl)benzoic acid
• CAS: 187840-93-3
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: QUMURYHKWMSVGN-UHFFFAOYSA-N

物化性质

• 沸点：
  375.6±22.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-Allyloxycarbonyl-ethyl)-benzoic acid 在 吗啉 、 四(三苯基膦)钯 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 50.0h， 生成
  参考文献：
  名称：

  Synthesis and biological activity of β-glucuronyl carbamate-based prodrugs of paclitaxel as potential candidates for ADEPT

  摘要：

  The syntheses of prodrugs of paclitaxel, which can be used in ADEPT in order to target paclitaxel towards tumor cells, are described. The prodrugs 1 and 2a,b consist of a spacer molecule connected via a carbamate linkage to a beta-glucuronic acid. The spacer molecule is also connected via an ester linkage to the 2'-OH of paclitaxel. Enzyme-catalyzed hydrolysis of the glucuronic acid moiety by human beta-glucuronidase results in the liberation of the parent drug paclitaxel via gamma or delta lactam formation with half-lives of 45 min and 2h (1 and 2h). The prodrugs 1 and 2b are two orders of magnitude less cytotoxic than paclitaxel. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00249-0
• 作为产物：
  描述：

  3-(2-羧基苯基)丙酸 、 烯丙醇 在 4-二甲氨基吡啶 、 N,N-二甲基甲酰胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以91%的产率得到2-(2-Allyloxycarbonyl-ethyl)-benzoic acid
  参考文献：
  名称：

  Synthesis and biological activity of β-glucuronyl carbamate-based prodrugs of paclitaxel as potential candidates for ADEPT

  摘要：

  The syntheses of prodrugs of paclitaxel, which can be used in ADEPT in order to target paclitaxel towards tumor cells, are described. The prodrugs 1 and 2a,b consist of a spacer molecule connected via a carbamate linkage to a beta-glucuronic acid. The spacer molecule is also connected via an ester linkage to the 2'-OH of paclitaxel. Enzyme-catalyzed hydrolysis of the glucuronic acid moiety by human beta-glucuronidase results in the liberation of the parent drug paclitaxel via gamma or delta lactam formation with half-lives of 45 min and 2h (1 and 2h). The prodrugs 1 and 2b are two orders of magnitude less cytotoxic than paclitaxel. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00249-0

文献信息

• Novel paclitaxel prodrugs, method for preparation as well as their use in selective chemotherapy
  申请人：PHARMACHEMIE B.V.

  公开号：EP0781778A1

  公开（公告）日：1997-07-02

  The invention relates to novel, water-soluble paclitaxel prodrugs wherein paclitaxel is, through its 2'-hydroxyl functionality, connected to a cleavable spacer group, which is in turn attached to a preferably enzymatically cleavable sugar group. Such prodrugs are relatively non-toxic and can be used in cancer treatment. They can be selectively activated at the tumor site by the action of endogeneous enzymes or targeted enzymes, or via a non-enzymatic process. The enzyme is preferably β-glucuronidase, β-glucosidase or β-galactosidase. The invention also relates to a process for preparing a pharmaceutical composition containing a paclitaxel prodrug as defined herein, which comprises said prodrug with a pharmaceutically acceptable carrier to provide a solid or liquid formulation for administration.

  本发明涉及新型水溶性紫杉醇原药，其中紫杉醇通过其 2'-羟基官能团与可裂解的间隔基团相连，而间隔基团又与优选的可酶裂解的糖基相连。这种原药相对无毒，可用于癌症治疗。它们可以通过内源酶或靶向酶的作用，或通过非酶过程，在肿瘤部位被选择性激活。酶最好是β-葡萄糖醛酸酶、β-葡萄糖苷酶或β-半乳糖苷酶。本发明还涉及一种制备含有本文定义的紫杉醇原药的药物组合物的工艺，该组合物由所述原药与药学上可接受的载体组成，以提供固体或液体给药制剂。
• Paclitaxel prodrugs, method for preparation as well as their use in selective chemotherapy
  申请人：PHARMACHEMIE B.V.

  公开号：EP0781778B1

  公开（公告）日：2002-04-17
• US5760072A
  申请人：——

  公开号：US5760072A

  公开（公告）日：1998-06-02