1-(3-acetylphenyl)-N-(2-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide | 1051930-03-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-acetylphenyl)-N-(2-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide
• 英文别名: 2-(3-acetylphenyl)-N-[(2-methoxyphenyl)methyl]-5-(trifluoromethyl)pyrazole-3-carboxamide
• CAS: 1051930-03-0
• 化学式: C₂₁H₁₈F₃N₃O₃
• 分子量: 417.387
• InChiKey: JPBDLJXIHIWWRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3-acetylphenyl)-N-(2-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide 、 N-Boc-N-甲基乙二胺 在 溶剂黄146 、 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 18.25h， 以30%的产率得到tert-butyl 2-(1-(3-(5-(2-methoxybenzylcarbamoyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)ethylamino)ethyl(methyl)carbamate
  参考文献：
  名称：

  1,2-Diamines as inhibitors of co-activator associated arginine methyltransferase 1 (CARM1)

  摘要：

  We have identified the N-1-benzyl-N-2-methylethane-1,2-diamine unit as a substitute for the (S)-alanine benzylamide moiety for the design of co-activator associated arginine methyltransferase 1 (CARM1) inhibitors. The potency of these inhibitors is in the same order of magnitude as their predecessors and their clearance, volume of distribution, and half lives were greatly improved. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.110
• 作为产物：
  描述：

  1-(3-(1-hydroxyethyl)phenyl)-N-(2-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到1-(3-acetylphenyl)-N-(2-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  1,2-Diamines as inhibitors of co-activator associated arginine methyltransferase 1 (CARM1)

  摘要：

  We have identified the N-1-benzyl-N-2-methylethane-1,2-diamine unit as a substitute for the (S)-alanine benzylamide moiety for the design of co-activator associated arginine methyltransferase 1 (CARM1) inhibitors. The potency of these inhibitors is in the same order of magnitude as their predecessors and their clearance, volume of distribution, and half lives were greatly improved. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.110

文献信息

• Amines as Small Molecule Inhibitors
  申请人：Wahhab Amal

  公开号：US20080280925A1

  公开（公告）日：2008-11-13

  The present invention relates to compounds that are useful as inhibitors of protein arginine methyltransferase that have a formula selected from Formula (I), Formula (II) and Formula (III), as well as racemic mixtures, diastereomers, enantiomers and tautomers thereof and N-oxides, hydrates, solvates, pharmaceutically acceptable salts, prodrugs and complexes thereof as defined herein. Said compound are useful as inhibitors of PRMTs and/or CARM-I. The invention further relates to compositions comprising such compounds and methods for their use.

  本发明涉及一种具有以下公式（I）、公式（II）和公式（III）之一的化合物，以及它们的外消旋混合物、对映异构体、恒定异构体和互变异构体以及N-氧化物、水合物、溶剂物、药学上可接受的盐、前药和复合物，其作为蛋白质精氨酸甲基转移酶抑制剂。所述化合物作为PRMTs和/或CARM-I的抑制剂具有用途。本发明还涉及包含这些化合物的组合物和它们的使用方法。
• Amines as small molecule inhibitors
  申请人：MethylGene Inc.

  公开号：US08338437B2

  公开（公告）日：2012-12-25

  The present invention relates to compounds that are useful as inhibitors of protein arginine methyltransferase that have a formula selected from Formula (I), Formula (II) and Formula (III), as well as racemic mixtures, diastereomers, enantiomers and tautomers thereof and N-oxides, hydrates, solvates, pharmaceutically acceptable salts, prodrugs and complexes thereof as defined herein. The compound are useful as inhibitors of PRMTs and/or CARM-I. The invention further relates to compositions comprising such compounds and methods for their use.

  本发明涉及一种化合物，其具有公式（I），公式（II）和公式（III）中选择的公式，以及它们的外消旋混合物，对映异构体，对映体和互变异构体以及N-氧化物，水合物，溶剂化物，药学上可接受的盐，前药和复合物，如本文所定义的，这些化合物可用作蛋白质精氨酸甲基转移酶的抑制剂和/或CARM-I。本发明还涉及包含这种化合物的组合物和使用它们的方法。
• WO2008/104077
  申请人：——

  公开号：——

  公开（公告）日：——
• SMALL MOLECULE INHIBITORS OF PROTEIN ARGININE METHYLTRANSFERASES (PRMTS)
  申请人：MethylGene Inc.

  公开号：EP2137158A1

  公开（公告）日：2009-12-30
• US8338437B2
  申请人：——

  公开号：US8338437B2

  公开（公告）日：2012-12-25