4-((diethylamino)ethyl)carbamoylbenzoic acid | 166523-16-6

• 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: 4-((diethylamino)ethyl)carbamoylbenzoic acid
• 英文别名: 4-([2-(N,N-diethylamino)ethyl]aminocarbonyl)benzoic acid；4-[2-(diethylamino)ethylcarbamoyl]benzoic acid
• CAS: 166523-16-6
• 化学式: C₁₄H₂₀N₂O₃
• mdl: MFCD12466769
• 分子量: 264.324
• InChiKey: JODWTMUWVHWPRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((diethylamino)ethyl)carbamoylbenzoic acid 在 氯化亚砜 作用下， 反应 1.0h， 生成 4-(2-Diethylamino-ethylcarbamoyl)-benzoyl chloride
  参考文献：
  名称：

  Titsch, U.; Mohammed, A.; Wagner, S., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 416 - 418

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯甲酰基苯甲酸甲酯 在 氢氧化钾 作用下， 反应 2.25h， 生成 4-((diethylamino)ethyl)carbamoylbenzoic acid
  参考文献：
  名称：

  Titsch, U.; Mohammed, A.; Wagner, S., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 416 - 418

  摘要：

  DOI：

文献信息

• Water soluble analogs and prodrugs of taxol
  申请人：Virginia Tech Intellectual Properties, Inc.

  公开号：US05411984A1

  公开（公告）日：1995-05-02

  Substituted 2'-benzoyl and 2', 7-dibenzoyl taxol derivatives are synthesized which have improved water solubility and stability while maintaining bioactivity. In a preferred embodiment, taxol 2',7-di(sodium 1,2-benzenedicarboxylate) is synthesized by reacting taxol with phthalic anhydride, and subsequently neutralizing the resulting acid by an ion exchange resin. Taxol 2'-(sodium 1,4-benzenedicarboxylate) is prepared by reacting the monobenzyl ester of 1,4-benzene dicarboxylic acid with taxol in the presence of dicyclohexyl carbodiimide and dimethylaminopyridine, hydrogenolysing the resulting ester to remove the benzyl group, and neutralizing with ion exchange resin. Other taxol prodrugs are prepared by modifications of these routes. In a preferred embodiment, the compounds prepared have improved water-solubility as compared with taxol and demonstrate activity in the M109 mouse bioassay system.

  合成了2'-苯甲酰和2'，7-二苯甲酰紫杉醇衍生物，其具有改善的水溶性和稳定性，同时保持生物活性。在一个优选实施例中，通过将紫杉醇与邻苯二甲酸酐反应，随后通过离子交换树脂中和产生的酸，合成了紫杉醇2'，7-二(钠1,2-苯二羧酸盐)。通过在邻苯二甲酸二苄酯存在下使用二环己基碳二亚胺和二甲基氨基吡啶与紫杉醇反应，氢解产生的酯以去除苄基，并使用离子交换树脂中和，制备了紫杉醇2'-(钠1,4-苯二羧酸盐)。通过这些途径的改变，制备了其他紫杉醇前药。在一个优选实施例中，制备的化合物与紫杉醇相比具有改善的水溶性，并在M109小鼠生物测定系统中表现出活性。
• Preliminary Studies of New Proteasome Inhibitors in the Tumor Targeting Approach: Synthesis and in Vitro Cytotoxicity
  作者：Magali Vivier、Anne-Sophie Jarrousse、Bernadette Bouchon、Marie-Josephe Galmier、Philippe Auzeloux、Jacques Sauzieres、Jean-Claude Madelmont

  DOI：10.1021/jm050181l

  日期：2005.10.1

  The proteasome is a multicatalytic protease that plays a critical role in the cell. The control of proteasomes could, thus, provide a weapon for the treatment of cancer. Therefore, we have synthesized six new peptide aldehyde inhibitors of the proteasome linked to the N-(2-diethylaminoethyl)benzamide (BZA-CO) structure, in order to target the cytotoxic activity to malignant melanoma cells. Biological studies demonstrated the influence of length and composition of the amino acid chain on the cytotoxicity of our compounds. Among them, compound 19 presents the highest cytotoxicity (IC50 = 0.64 +/- 0.07 mu mol): this cytotoxicity was maintained in the presence of BZA-CO but decreased 8-fold compared to the control MG132. Fluorescence activated cell sorter (FACS) and cytotoxic activity analysis demonstrated the selectivity of compound 19 for melanoma cells. Finally, western blottings of ubiquitinated proteins in IPC227F cells as well as proteasome assays confirmed that the cytotoxicity was linked to an inhibition of the proteasome activity.
• US5411984A
  申请人：——

  公开号：US5411984A

  公开（公告）日：1995-05-02