N-(2-(1H-benzo[d]imidazol-2-yl)ethyl)acetamide | 686736-24-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-(1H-benzo[d]imidazol-2-yl)ethyl)acetamide
• 英文别名: N-(2-(1H-benzimidazole-2-yl)ethyl)acetamide；N-(2-(1H-benzimidazol-2-yl)ethyl)acetamide；N-[2-(1H-benzimidazol-2-yl)ethyl]acetamide
• CAS: 686736-24-3
• 化学式: C₁₁H₁₃N₃O
• mdl: MFCD00522698
• 分子量: 203.244
• InChiKey: VYTQKASBEONUKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻苯二胺 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 生成 N-(2-(1H-benzo[d]imidazol-2-yl)ethyl)acetamide
  参考文献：
  名称：

  Design, synthesis, and enzyme kinetics of novel benzimidazole and quinoxaline derivatives as methionine synthase inhibitors

  摘要：

  Methionine synthase catalyzes the transfer of a methyl group from 5-methyltetrahydrofolate to homocysteine, producing methionine and tetrahydrofolate. Benzimidazole and deazatetrahydrofolates derivatives have been shown to inhibit methionine synthase by competing with the substrate 5-methyltetrahydrofolate. In this study, a novel series of substituted benzimidazoles and quinoxalines were designed and assessed for inhibitory activity against purified rat liver methionine synthase using a radiometric enzyme assay. Compounds 3g, 3j, and 5c showed the highest activity against methionine synthase (IC50: 20 mu M, 18 mu M, 9 mu M, respectively). Kinetic analysis of these compounds using Lineweaver-Burk plots revealed characteristics of mixed inhibition for 3g and 5c; and uncompetitive inhibition for 3j. Docking study into a homology model of the rat methionine synthase gave insights into the molecular determinants of the activity of this class of compounds. The identification of these drug-like inhibitors could lead the design of the next generation modulators of methionine synthase. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.052

文献信息

• Substituted 6,5-Fused Bicyclic Heteroaryl Compounds
  申请人：Epizyme, Inc.

  公开号：US20140296283A1

  公开（公告）日：2014-10-02

  The present invention relates to azole bicyclic heteroaryl compounds. The present invention also relates to pharmaceutical compositions containing these compounds and methods of treating cancer by administering these compounds and pharmaceutical compositions to subjects in need thereof. The present invention also relates to the use of such compounds for research or other non-therapeutic purposes.

  本发明涉及杂环双环杂芳基化合物。本发明还涉及含有这些化合物的药物组合物以及通过将这些化合物和药物组合物用于需要的受试者治疗癌症的方法。本发明还涉及将这些化合物用于研究或其他非治疗目的的使用。
• Substituted 6, 5-Fused Bicyclic Heteroaryl Compounds
  申请人：EPIZYME, INC.

  公开号：US20150246916A1

  公开（公告）日：2015-09-03

  The present invention relates to azole bicyclic heteroaryl compounds. The present invention also relates to pharmaceutical compositions containing these compounds and methods of treating cancer by administering these compounds and pharmaceutical compositions to subjects in need thereof. The present invention also relates to the use of such compounds for research or other non-therapeutic purposes.

  本发明涉及杂环双环杂芳烃化合物。本发明还涉及含有这些化合物的药物组合物以及通过将这些化合物和药物组合物用于需要的受试者治疗癌症的方法。本发明还涉及将这些化合物用于研究或其他非治疗目的的用途。
• Synthesis, Biological Evaluation, and Structure–Activity Relationships of Potent Noncovalent and Nonpeptidic Cruzain Inhibitors as Anti-<i>Trypanosoma cruzi</i> Agents
  作者：Rafaela S. Ferreira、Marco A. Dessoy、Ivani Pauli、Mariana L. Souza、Renata Krogh、Ana I. L. Sales、Glaucius Oliva、Luiz C. Dias、Adriano D. Andricopulo

  DOI：10.1021/jm401709b

  日期：2014.3.27

  The development of cruzain inhibitors has been driven by the urgent need to develop novel and more effective drugs for the treatment of Chagas' disease. Herein, we report the lead optimization of a class of noncovalent cruzain inhibitors, starting from an inhibitor previously cocrystallized with the enzyme (K(i) = 0.8 μM). With the goal of achieving a better understanding of the structure-activity relationships, we have synthesized and evaluated a series of over 40 analogues, leading to the development of a very promising competitive inhibitor (8r, IC50 = 200 nM, K(i) = 82 nM). Investigation of the in vitro trypanocidal activity and preliminary cytotoxicity revealed the potential of the most potent cruzain inhibitors in guiding further medicinal chemistry efforts to develop drug candidates for Chagas' disease.
• US9045477B2
  申请人：——

  公开号：US9045477B2

  公开（公告）日：2015-06-02
• US9365570B2
  申请人：——

  公开号：US9365570B2

  公开（公告）日：2016-06-14