2-{3,5-bis(trifluoromethyl)benzamido}benzoic acid | 1053954-74-7

• 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: 2-{3,5-bis(trifluoromethyl)benzamido}benzoic acid
• 英文别名: 2-(3,5-Bis(trifluoromethyl)benzamido)benzoic acid；2-[[3,5-bis(trifluoromethyl)benzoyl]amino]benzoic acid
• CAS: 1053954-74-7
• 化学式: C₁₆H₉F₆NO₃
• 分子量: 377.243
• InChiKey: DOQBWXZFOZWSJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-{3,5-bis(trifluoromethyl)benzamido}benzoic acid 、 对氯苯胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-(2-(4-chlorophenylcarbamoyl)phenyl)-3,5-bis(trifluoromethyl)benzamide
  参考文献：
  名称：

  Design, synthesis and prostate cancer cell-based studies of analogs of the Rho/MKL1 transcriptional pathway inhibitor, CCG-1423

  摘要：

  We recently identified bis(amide) CCG-1423 (1) as a novel inhibitor of RhoA/C-mediated gene transcription that is capable of inhibiting invasion of PC-3 prostate cancer cells in a Matrigel model of metastasis. An initial structure-activity relationship study focusing on bioisosteric replacement of the amides and conformational restriction identified two compounds, 4g and 8, with improved selectivity for inhibition of RhoA/C-mediated gene transcription and attenuated cytotoxicity relative to 1. Both compounds were also capable of inhibiting cell invasion with equal efficacy to 1 but with less attendant cytotoxicity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.056
• 作为产物：
  描述：

  3-{3,5-bis(trifluoromethyl)phenyl}-1,4,2-dioxazol-5-one 、 苯甲酸 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 lithium acetate 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以62%的产率得到2-{3,5-bis(trifluoromethyl)benzamido}benzoic acid
  参考文献：
  名称：

  机制驱动的方法通过IrIII催化开发轻度和多功能的CH酰胺化反应

  摘要：

  本文描述了一种基于机制的方法，用于在Ir III催化下开发通用的CH酰胺化方案。关键的C-N偶联步骤与酰基叠氮化物和1,4,2-二恶唑5-1的反应动力学使我们得出结论，二恶唑酮在介导环环中间体形成碳氮键方面更为有效。计算分析表明，较高反应性的起源是异步脱羧运动，这可能促进Ir-酰亚胺基物种的形成。重要的是，化学计量反应性已成功转化为多种底物（18种不同类型）的催化活性，其中许多底物被认为对功能化具有挑战性。新方法的应用可以实现药物分子的后期功能化。

  DOI：

  10.1002/chem.201702397

文献信息

• METHODS AND COMPOSITIONS FOR MODULATING RHO-MEDIATED GENE TRANSCRIPTION
  申请人：Neubig Richard

  公开号：US20120252792A1

  公开（公告）日：2012-10-04

  The invention provides methods, compositions, and kits for the inhibition of members of the Rho GTPase family. Specifically, the invention provides methods, compositions and kits for the inhibition of RhoA and/or RhoC transcriptional signalling. The invention finds use in treatment of Rho-mediated disease states (e.g., tumor metastasis, inflammation, inflammatory disease), Rho-mediated biological conditions, and in cell signaling research.

  本发明提供了抑制Rho GTPase家族成员的方法、组合物和试剂盒。具体来说，本发明提供了抑制RhoA和/或RhoC转录信号的方法、组合物和试剂盒。本发明可用于治疗Rho介导的疾病状态（例如肿瘤转移、炎症、炎症性疾病）、Rho介导的生物条件以及细胞信号研究。
• [EN] METHODS AND COMPOSITIONS FOR INHIBITING RHO-MEDIATED DISEASES AND CONDITIONS<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR INHIBER DES MALADIES ET DES ÉTATS À MÉDIATION PAR RHO
  申请人：UNIV MICHIGAN

  公开号：WO2011035143A2

  公开（公告）日：2011-03-24

  The invention provides methods, compositions, and kits for the inhibition of members of the Rho GTPase family. Specifically, the invention provides methods, compositions and kits for the inhibition of RhoA and/or RhoC transcriptional signalling. The invention finds use in treatment of Rho-mediated disease states (e.g., tumor metastasis, inflammation, inflammatory disease), Rho-mediated biological conditions, and in cell signaling research.
• Design, synthesis and prostate cancer cell-based studies of analogs of the Rho/MKL1 transcriptional pathway inhibitor, CCG-1423
  作者：Chris R. Evelyn、Jessica L. Bell、Jenny G. Ryu、Susan M. Wade、Andrew Kocab、Nicole L. Harzdorf、H.D. Hollis Showalter、Richard R. Neubig、Scott D. Larsen

  DOI：10.1016/j.bmcl.2009.11.056

  日期：2010.1

  We recently identified bis(amide) CCG-1423 (1) as a novel inhibitor of RhoA/C-mediated gene transcription that is capable of inhibiting invasion of PC-3 prostate cancer cells in a Matrigel model of metastasis. An initial structure-activity relationship study focusing on bioisosteric replacement of the amides and conformational restriction identified two compounds, 4g and 8, with improved selectivity for inhibition of RhoA/C-mediated gene transcription and attenuated cytotoxicity relative to 1. Both compounds were also capable of inhibiting cell invasion with equal efficacy to 1 but with less attendant cytotoxicity. (C) 2009 Elsevier Ltd. All rights reserved.
• Mechanism-Driven Approach To Develop a Mild and Versatile C−H Amidation through Ir^IIICatalysis
  作者：Yeongyu Hwang、Yoonsu Park、Sukbok Chang

  DOI：10.1002/chem.201702397

  日期：2017.8.16

  catalysis. Reaction kinetics of a key C−N coupling step with acyl azide and 1,4,2‐dioxazol‐5‐one led us to conclude that dioxazolones are much more efficient in mediating the formation of a carbon−nitrogen bond from an iridacyclic intermediate. Computational analysis revealed that the origin of higher reactivity is asynchronous decarboxylation motion, which may facilitate the formation of Ir‐imido species

  本文描述了一种基于机制的方法，用于在Ir III催化下开发通用的CH酰胺化方案。关键的C-N偶联步骤与酰基叠氮化物和1,4,2-二恶唑5-1的反应动力学使我们得出结论，二恶唑酮在介导环环中间体形成碳氮键方面更为有效。计算分析表明，较高反应性的起源是异步脱羧运动，这可能促进Ir-酰亚胺基物种的形成。重要的是，化学计量反应性已成功转化为多种底物（18种不同类型）的催化活性，其中许多底物被认为对功能化具有挑战性。新方法的应用可以实现药物分子的后期功能化。