methyl 4-(((diethylamino)ethyl)carbamoyl)benzoate | 869805-60-7

• 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: methyl 4-(((diethylamino)ethyl)carbamoyl)benzoate
• 英文别名: Methyl 4-[2-(diethylamino)ethylcarbamoyl]benzoate
• CAS: 869805-60-7
• 化学式: C₁₅H₂₂N₂O₃
• 分子量: 278.351
• InChiKey: WNEAKFAYFLDGDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(((diethylamino)ethyl)carbamoyl)benzoate 在 氢氧化钾 作用下， 反应 2.0h， 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：
• 作为产物：
  描述：

  4-氯甲酰基苯甲酸甲酯 、 N,N-二乙基乙二胺 反应 0.25h， 生成 methyl 4-(((diethylamino)ethyl)carbamoyl)benzoate
  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

• Design, synthesis and evaluation of antiproliferative activity of melanoma-targeted histone deacetylase inhibitors
  作者：Idris Raji、Kabir Ahluwalia、Adegboyega K. Oyelere

  DOI：10.1016/j.bmcl.2017.01.044

  日期：2017.2

  The clinical validation of histone deacetylase inhibition as a cancer therapeutic modality has stimulated interest in the development of new generation of potent and tumor selective histone deacetylase inhibitors (HDACi). With the goal of selective delivery of the HDACi to melanoma cells, we incorporated the benzamide, a high affinity melanin-binding template, into the design of HDACi to generate a new

  组蛋白脱乙酰基酶抑制作为一种癌症治疗方法的临床验证激发了人们对新一代有效和肿瘤选择性组蛋白脱乙酰基酶抑制剂（HDACi）的开发兴趣。为了选择性地将HDACi递送至黑素瘤细胞，我们将苯甲酰胺（一种高亲和力的黑色素结合模板）整合到HDACi的设计中，以生成一系列新的化合物10a-b和11a-b，它们对HDAC1和HDAC6。但是，相对于未靶向的HDACi，这些化合物的抗增殖活性减弱。化合物14提供了另一种策略，一种带有苯甲酰胺模板的前药，该模板通过不稳定键与基于异羟肟酸酯的HDACi连接。这种前药化合物显示出有希望的抗增殖活性，值得进一步研究。
• 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.