3-acetyl-5-((1-(4-fluorophenyl)ethyl)carbamoyl)benzoic acid | 924650-39-5

• 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: 3-acetyl-5-((1-(4-fluorophenyl)ethyl)carbamoyl)benzoic acid
• 英文别名: 3-acetyl-5-[1-(4-fluorophenyl)ethylcarbamoyl]benzoic acid
• CAS: 924650-39-5
• 化学式: C₁₈H₁₆FNO₄
• 分子量: 329.328
• InChiKey: NTSUAULCPDRSGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetyl-5-((1-(4-fluorophenyl)ethyl)carbamoyl)benzoic acid 、 tert-butyl 3-methoxybenzyl((2R,3S)-3-amino-4-(3,5-difluorophenyl)-2-hydroxybutyl)-carbamate 在 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [(2R,3S)-3-{3-Acetyl-5-[1-(4-fluoro-phenyl)-ethylcarbamoyl]-benzoylamino}-4-(3,5-difluoro-phenyl)-2-hydroxy-butyl]-(3-methoxy-benzyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and SAR of hydroxyethylamine based phenylcarboxyamides as inhibitors of BACE

  摘要：

  A series of N-((2S,3R)-1-(3,5-difluorophenyl)-3-hydroxy-4-(3-methoxybenzylamino)-butan-2-yl)benzamides has been synthesized as BACE inhibitors. A variety of P2 and P3 substituents has been explored, and these efforts have culminated in the identification of several 1,3,5-trisubstituted phenylcarboxyamides with potent BACE inhibitory activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.144
• 作为产物：
  描述：

  methyl 3-acetyl-5-((1-(4-fluorophenyl)ethyl)-carbamoyl)benzoate 在 甲醇 、 lithium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以96%的产率得到3-acetyl-5-((1-(4-fluorophenyl)ethyl)carbamoyl)benzoic acid
  参考文献：
  名称：

  Novel phenylcarboxyamides as beta-secretase inhibitors

  摘要：

  提供了一系列新颖的苯基羧酰胺化合物，其化学式为（I）或其立体异构体；或其药用可接受的盐，其中R1、R2、R3、X和Y的定义如本文所述，它们的药物组成和使用方法。这些新颖化合物抑制β-分泌酶对淀粉样前体蛋白（APP）的加工，更具体地说，抑制Aβ肽的产生。本公开涉及对β-淀粉样蛋白产生相关的神经系统疾病的治疗中有用的化合物，如阿尔茨海默病和其他受抗淀粉样活性影响的疾病。

  公开号：

  US20070032470A1

文献信息

• Phenylcarboxyamides as beta-secretase inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US07476764B2

  公开（公告）日：2009-01-13

  There is provided a series of novel phenylcarboxyamides of Formula (I) or a stereoisomer; or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, X and Y as defined herein, their pharmaceutical compositions and methods of use. These novel compounds inhibit the processing of amyloid precursor protein (APP) by β-secretase and, more specifically, inhibit the production of Aβ-peptide. The present disclosure is directed to compounds useful in the treatment of neurological disorders related to β-amyloid production, such as Alzheimer's disease and other conditions affected by anti-amyloid activity.

  提供了一系列新型苯基羧酰胺化合物的公式（I）或立体异构体；或其药学上可接受的盐。其中，R1、R2、R3、X和Y的定义如本文所述，以及它们的药物组合物和使用方法。这些新化合物通过β-分泌酶抑制淀粉样前体蛋白（APP）的处理，更具体地抑制Aβ-肽的产生。本公开涉及在治疗与β-淀粉样蛋白产生有关的神经系统疾病，如阿尔茨海默病和其他受抗淀粉样蛋白活性影响的疾病中有用的化合物。
• US7476764B2
  申请人：——

  公开号：US7476764B2

  公开（公告）日：2009-01-13
• Novel phenylcarboxyamides as beta-secretase inhibitors
  申请人：Wu Yong-Jin

  公开号：US20070032470A1

  公开（公告）日：2007-02-08

  There is provided a series of novel phenylcarboxyamides of Formula (I) or a stereoisomer; or a pharmaceutically acceptable salt thereof, wherein R 1 , R 2 , R 3 , X and Y as defined herein, their pharmaceutical compositions and methods of use. These novel compounds inhibit the processing of amyloid precursor protein (APP) by β-secretase and, more specifically, inhibit the production of Aβ-peptide. The present disclosure is directed to compounds useful in the treatment of neurological disorders related to β-amyloid production, such as Alzheimer's disease and other conditions affected by anti-amyloid activity.

  提供了一系列新颖的苯基羧酰胺化合物，其化学式为（I）或其立体异构体；或其药用可接受的盐，其中R1、R2、R3、X和Y的定义如本文所述，它们的药物组成和使用方法。这些新颖化合物抑制β-分泌酶对淀粉样前体蛋白（APP）的加工，更具体地说，抑制Aβ肽的产生。本公开涉及对β-淀粉样蛋白产生相关的神经系统疾病的治疗中有用的化合物，如阿尔茨海默病和其他受抗淀粉样活性影响的疾病。
• Synthesis and SAR of hydroxyethylamine based phenylcarboxyamides as inhibitors of BACE
  作者：Yong-Jin Wu、Yunhui Zhang、Andrew C. Good、Catherine R. Burton、Jeremy H. Toyn、Charles F. Albright、John E. Macor、Lorin A. Thompson

  DOI：10.1016/j.bmcl.2009.03.144

  日期：2009.5

  A series of N-((2S,3R)-1-(3,5-difluorophenyl)-3-hydroxy-4-(3-methoxybenzylamino)-butan-2-yl)benzamides has been synthesized as BACE inhibitors. A variety of P2 and P3 substituents has been explored, and these efforts have culminated in the identification of several 1,3,5-trisubstituted phenylcarboxyamides with potent BACE inhibitory activity. (C) 2009 Elsevier Ltd. All rights reserved.