4-(benzhydrylamino)benzoic acid | 72417-88-0

• 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-(benzhydrylamino)benzoic acid
• CAS: 72417-88-0
• 化学式: C₂₀H₁₇NO₂
• 分子量: 303.36
• InChiKey: ZNRARLQWOJSMPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(benzhydrylamino)benzoic acid 、 间氨基苯甲酸 在 COMU 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以18%的产率得到3-(4-(benzhydrylamino)benzamido)benzoic acid
  参考文献：
  名称：

  8-Hydroxyquinoline-based inhibitors of the Rce1 protease disrupt Ras membrane localization in human cells

  摘要：

  Ras converting enzyme 1 (Rce1) is an endoprotease that catalyzes processing of the C-terminus of Ras protein by removing -aaX from the CaaX motif. The activity of Rce1 is crucial for proper localization of Ras to the plasma membrane where it functions. Ras is responsible for transmitting signals related to cell proliferation, cell cycle progression, and apoptosis. The disregulation of these pathways due to constitutively active oncogenic Ras can ultimately lead to cancer. Ras, its effectors and regulators, and the enzymes that are involved in its maturation process are all targets for anti-cancer therapeutics. Key enzymes required for Ras maturation and localization are the farnesyltransferase (FTase), Rce1, and isoprenylcysteine carboxyl methyltransferase (ICMT). Among these proteins, the physiological role of Rce1 in regulating Ras and other CaaX proteins has not been fully explored. Small-molecule inhibitors of Rce1 could be useful as chemical biology tools to understand further the downstream impact of Rce1 on Ras function and serve as potential leads for cancer therapeutics. Structure-activity relationship (SAR) analysis of a previously reported Rce1 inhibitor, NSC1011, has been performed to generate a new library of Rce1 inhibitors. The new inhibitors caused a reduction in Rce1 in vitro activity, exhibited low cell toxicity, and induced mislocalization of EGFP-Ras from the plasma membrane in human colon carcinoma cells giving rise to a phenotype similar to that observed with siRNA knockdowns of Rce1 expression. Several of the new inhibitors were more effective at mislocalizing K-Ras compared to a potent farnesyltransferase inhibitor (FTI), which is significant because of the preponderance of K-Ras mutations in cancer. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.043
• 作为产物：
  描述：

  ethyl 4-(benzhydrylamino)benzoate 在 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 8.0h， 以88%的产率得到4-(benzhydrylamino)benzoic acid
  参考文献：
  名称：

  8-Hydroxyquinoline-based inhibitors of the Rce1 protease disrupt Ras membrane localization in human cells

  摘要：

  Ras converting enzyme 1 (Rce1) is an endoprotease that catalyzes processing of the C-terminus of Ras protein by removing -aaX from the CaaX motif. The activity of Rce1 is crucial for proper localization of Ras to the plasma membrane where it functions. Ras is responsible for transmitting signals related to cell proliferation, cell cycle progression, and apoptosis. The disregulation of these pathways due to constitutively active oncogenic Ras can ultimately lead to cancer. Ras, its effectors and regulators, and the enzymes that are involved in its maturation process are all targets for anti-cancer therapeutics. Key enzymes required for Ras maturation and localization are the farnesyltransferase (FTase), Rce1, and isoprenylcysteine carboxyl methyltransferase (ICMT). Among these proteins, the physiological role of Rce1 in regulating Ras and other CaaX proteins has not been fully explored. Small-molecule inhibitors of Rce1 could be useful as chemical biology tools to understand further the downstream impact of Rce1 on Ras function and serve as potential leads for cancer therapeutics. Structure-activity relationship (SAR) analysis of a previously reported Rce1 inhibitor, NSC1011, has been performed to generate a new library of Rce1 inhibitors. The new inhibitors caused a reduction in Rce1 in vitro activity, exhibited low cell toxicity, and induced mislocalization of EGFP-Ras from the plasma membrane in human colon carcinoma cells giving rise to a phenotype similar to that observed with siRNA knockdowns of Rce1 expression. Several of the new inhibitors were more effective at mislocalizing K-Ras compared to a potent farnesyltransferase inhibitor (FTI), which is significant because of the preponderance of K-Ras mutations in cancer. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.043

文献信息

• Cobalt(II)/TPPMS-Catalyzed Dehydrative Nucleophilic Substitution of Alcohols in Water
  作者：Hidemasa Hikawa、Yukiko Ijichi、Shoko Kikkawa、Isao Azumaya

  DOI：10.1002/ejoc.201601501

  日期：2017.1.18

  A green and sustainable direct dehydrative amination of alcohols, catalyzed by cobalt(II)/TPPMS (sodium diphenylphosphinobenzene‐3‐sulfonate) in water, is described.

  描述了在水中钴（II）/ TPPMS（二苯基膦基苯-3-磺酸钠）催化的绿色环保且可持续的醇直接脱水胺化反应。
• Synthesis of Aminobenzoic Acid Derivatives via Chemoselective Carbene Insertion into the −NH Bond Catalyzed by Cu(I) Complex
  作者：Kankanala Ramakrishna、Chinnappan Sivasankar

  DOI：10.1021/acs.joc.6b01249

  日期：2016.8.5

  Phosphine ligand stabilized air-stable Cu(I) complexes have been successfully used to functionalize the aromatic aminobenzoic acids in a chemoselective manner without implementing protection and deprotection strategy under mild reaction conditions. This chemoselective carbene insertion into −NH bond over −COOH and −OH bonds leads to the wide range of carboxy and hydroxy functionalized α-amino esters

  膦配体稳定的空气稳定的Cu（I）络合物已成功用于以化学选择性方式官能化芳族氨基苯甲酸，而无需在温和的反应条件下实施保护和脱保护策略。这种化学选择性卡宾插入-COOH和-OH键上方的-NH键会导致羧基和羟基官能化的α-氨基酯类化合物的广泛应用（27个例子）。所有分离出的新产品均已使用标准分析方法进行了充分表征。
• Chemoselective Benzylation of Unprotected Anthranilic Acids with Benzhydryl Alcohols by Water-Soluble Au(III)/TPPMS in Water
  作者：Hidemasa Hikawa、Hideharu Suzuki、Yuusaku Yokoyama、Isao Azumaya

  DOI：10.1021/jo401064f

  日期：2013.7.5

  A novel and efficient method for the benzylation of unprotected anthranilic acids with benzhydryl alcohols using water-soluble Au(III)/TPPMS in water is developed. Water plays an important role in our catalytic system. This new protocol could be used for not only N-benzylation, but also chemoselective C-benzylation by the Friedel-Crafts reaction.
• [EN] COMPOUNDS AND METHODS FOR MODULATING G PROTEIN-COUPLED RECEPTORS<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR MODULER DES RÉCEPTEURS COUPLÉS À LA PROTÉINE G
  申请人：IRM LLC

  公开号：WO2008121570A1

  公开（公告）日：2008-10-09

  [EN] The invention provides methods for modulating G protein-coupled receptor 20 (GPR20), and methods for using such compounds to treat, ameliorate or prevent a condition associated with abnormal or deregulated GPR20.
  [FR] L'invention concerne des procédés pour moduler un récepteur couplé à la protéine G 20 (GPR 20), et des procédés pour utiliser de tels composés pour traiter, améliorer empêcher un état associé à un GPR 20 ou anormal déréglé.