(5-(aminomethyl)thiophen-2-yl)boronic acid | 947281-56-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (5-(aminomethyl)thiophen-2-yl)boronic acid
• 英文别名: [5-(Aminomethyl)thiophen-2-yl]boronic acid；[5-(aminomethyl)thiophen-2-yl]boronic acid
• CAS: 947281-56-3
• 化学式: C₅H₈BNO₂S
• 分子量: 157.001
• InChiKey: DSUFKAVGRIZEGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.11
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  94.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [4-[(3-Chloro-4-fluorophenyl)carbamoyl-(2-pyrrolidin-1-ylethyl)amino]cyclohexen-1-yl] trifluoromethanesulfonate 、 (5-(aminomethyl)thiophen-2-yl)boronic acid 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride sodium carbonate 、 lithium chloride 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 1.17h， 生成 1-(4-(5-(Aminomethyl)thiophen-2-yl)cyclohex-3-enyl)-3-(3-chloro-4-fluorophenyl)-1-(2-(pyrrolidin-1-yl)ethyl)urea
  参考文献：
  名称：

  SAR study of bicyclo[4.1.0]heptanes as melanin-concentrating hormone receptor R1 antagonists: Taming hERG

  摘要：

  To improve the ex vivo potency of MCH inhibitor la and to address its hERG liability, a structure-activity study was carried out, focusing on three regions of the lead structure. Introduction of new side chains with basic nitrogen improved in vitro and ex vivo bindings. Many potent compounds with K-i < 10 nM were discovered (compounds 6a-j) and several Compounds (14-17) had excellent ex vivo binding at 6 h and 24 h. Attenuating the basicity of nitrogen on the side chain, and in particular, introduction of a polar group such as aminomethyl on the distal phenyl ring significantly lowered the hERG activity. Further replacement of the distal phenyl group with heteroaryl groups in the cyclohexene series provided compounds such as 281 with excellent ex vivo activity with much reduced hERG liability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.068
• 作为产物：
  描述：

  5-醛基-2-噻吩硼酸 在 氨 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 乙二醇二甲醚 为溶剂， 生成 (5-(aminomethyl)thiophen-2-yl)boronic acid
  参考文献：
  名称：

  [EN] NOVEL FUSED TRIAZOLONES AND THE USES THEREOF
  [FR] TRIAZOLONES FUSIONNEES ET UTILISATIONS DE CELLES-CI

  摘要：

  这项发明涉及具有结构图（I）的新化合物，以及它们的药物组合物和使用方法。这些新化合物可用于治疗或预防癌症。

  公开号：

  WO2004081008A1

文献信息

• Discovery of Highly Selective Inhibitors of the Human Constitutive Proteasome β5c Chymotryptic Subunit
  作者：Wenhu Zhan、Daqiang Li、Priya Saha、Rong Wang、Hao Zhang、Amrendra K. Ajay、Christa Deban、George Sukenick、Jamil Azzi、Gang Lin

  DOI：10.1021/acs.jmedchem.2c00733

  日期：2023.1.26

  We describe our discovery and development of potent and highly selective inhibitors of human constitutive proteasome chymotryptic activity (β5c). Structure–activity relationship studies of the novel class of inhibitors focused on optimization of N-cap, C-cap, and side chain of the chemophore asparagine. Compound 32 is the most potent and selective β5c inhibitor in this study. A docking study provides

  我们描述了我们对人类组成型蛋白酶体胰凝乳蛋白酶活性 (β5c) 的有效且高选择性抑制剂的发现和开发。新型抑制剂的构效关系研究重点是化学基团天冬酰胺的N帽、 C帽和侧链的优化。化合物32是本研究中最有效、最具选择性的 β5c 抑制剂。对接研究为效力和选择性提供了结构原理。动力学研究显示了可逆且非竞争性的抑制机制。它进入细胞与蛋白酶体靶标结合，通过与 β5i 选择性抑制剂协同作用，有效选择性地杀死多发性骨髓瘤细胞。
• SAR study of bicyclo[4.1.0]heptanes as melanin-concentrating hormone receptor R1 antagonists: Taming hERG
  作者：Jing Su、Brian A. McKittrick、Haiqun Tang、Duane A. Burnett、John W. Clader、William J. Greenlee、Brian E. Hawes、Kim O’Neill、Brian Spar、Blair Weig、Timothy Kowalski、Steve Sorota、Cheng Li、Tongtong Liu

  DOI：10.1016/j.bmc.2007.05.068

  日期：2007.8

  To improve the ex vivo potency of MCH inhibitor la and to address its hERG liability, a structure-activity study was carried out, focusing on three regions of the lead structure. Introduction of new side chains with basic nitrogen improved in vitro and ex vivo bindings. Many potent compounds with K-i < 10 nM were discovered (compounds 6a-j) and several Compounds (14-17) had excellent ex vivo binding at 6 h and 24 h. Attenuating the basicity of nitrogen on the side chain, and in particular, introduction of a polar group such as aminomethyl on the distal phenyl ring significantly lowered the hERG activity. Further replacement of the distal phenyl group with heteroaryl groups in the cyclohexene series provided compounds such as 281 with excellent ex vivo activity with much reduced hERG liability. (c) 2007 Elsevier Ltd. All rights reserved.
• [EN] NOVEL FUSED TRIAZOLONES AND THE USES THEREOF<br/>[FR] TRIAZOLONES FUSIONNEES ET UTILISATIONS DE CELLES-CI
  申请人：ASTRAZENECA AB

  公开号：WO2004081008A1

  公开（公告）日：2004-09-23

  This invention relates to novel compounds having the structural diagram (I) and to their pharmaceutical compositions and to their methods of use. These novel compounds provide a treatment or prophylaxis of cancer.

  这项发明涉及具有结构图（I）的新化合物，以及它们的药物组合物和使用方法。这些新化合物可用于治疗或预防癌症。