5-(4-aminophenyl)furan-2-carboxylic acid ((S)-1-cyclohexyl-2-methylaminomethyl)amide | 1227193-47-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-(4-aminophenyl)furan-2-carboxylic acid ((S)-1-cyclohexyl-2-methylaminomethyl)amide
• 英文别名: 5-(4-aminophenyl)-N-[(1S)-1-cyclohexyl-2-(methylamino)-2-oxoethyl]furan-2-carboxamide
• CAS: 1227193-47-6
• 化学式: C₂₀H₂₅N₃O₃
• 分子量: 355.437
• InChiKey: PVOGSXOXDQENFD-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  97.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-aminophenyl)furan-2-carboxylic acid ((S)-1-cyclohexyl-2-methylaminomethyl)amide 、 5-甲基-1H-吡唑-3-羧酸 在 N,N-二异丙基乙胺 、 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 Furan-2-carboxamide deriv., 9
  参考文献：
  名称：

  Improving potency and selectivity of a new class of non-Zn-chelating MMP-13 inhibitors

  摘要：

  Discovery and optimization of potency and selectivity of a non-Zn-chelating MMP-13 inhibitor with the aid of protein co-crystal structural information is reported. This inhibitor was observed to have a binding mode distinct from previously published MMP-13 inhibitors. Potency and selectivity were improved by extending the hit structure out from the active site into the S1' pocket. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.151
• 作为产物：
  描述：

  5-(4-nitrophenyl)furan-2-carboxylic acid ((S)-cyclohexylmethylcarbamoylmethyl)amide 在 溶剂黄146 、 锌 作用下， 反应 0.5h， 生成 5-(4-aminophenyl)furan-2-carboxylic acid ((S)-1-cyclohexyl-2-methylaminomethyl)amide
  参考文献：
  名称：

  [EN] HETEROARYL DIAMIDE COMPOUNDS USEFUL AS MMP-13 INHIBITORS
  [FR] COMPOSÉS HÉTÉROARYL-DIAMIDE UTILES EN TANT QU'INHIBITEURS DE MMP-13

  摘要：

  公开号：

  WO2010056585A3

文献信息

• Heteroaryl Diamide Compounds Useful as MMP-13 Inhibitors
  申请人：Farrow Neil Alexander

  公开号：US20110275625A1

  公开（公告）日：2011-11-10

  Disclosed are compounds and compositions of the formula (I) as described herein which are inhibitors of MMP-13. Also disclosed are methods of using and making compounds of the formula (I).

  本文披露了公式（I）所描述的化合物和组合物，它们是MMP-13的抑制剂。还披露了使用和制备公式（I）化合物的方法。
• HETEROARYL DIAMIDE COMPOUNDS USEFUL AS MMP-13 INHIBITORS
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2346831B1

  公开（公告）日：2015-01-07
• US8637550B2
  申请人：——

  公开号：US8637550B2

  公开（公告）日：2014-01-28
• [EN] HETEROARYL DIAMIDE COMPOUNDS USEFUL AS MMP-13 INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROARYL-DIAMIDE UTILES EN TANT QU'INHIBITEURS DE MMP-13
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2010056585A3

  公开（公告）日：2010-11-25
• Improving potency and selectivity of a new class of non-Zn-chelating MMP-13 inhibitors
  作者：Alexander Heim-Riether、Steven J. Taylor、Shuang Liang、Donghong Amy Gao、Zhaoming Xiong、E. Michael August、Brandon K. Collins、Bennett T. Farmer、Kathleen Haverty、Melissa Hill-Drzewi、Hans-Dieter Junker、S. Mariana Margarit、Neil Moss、Thomas Neumann、John R. Proudfoot、Lana Smith Keenan、Renate Sekul、Qiang Zhang、Jun Li、Neil A. Farrow

  DOI：10.1016/j.bmcl.2009.07.151

  日期：2009.9

  Discovery and optimization of potency and selectivity of a non-Zn-chelating MMP-13 inhibitor with the aid of protein co-crystal structural information is reported. This inhibitor was observed to have a binding mode distinct from previously published MMP-13 inhibitors. Potency and selectivity were improved by extending the hit structure out from the active site into the S1' pocket. (C) 2009 Elsevier Ltd. All rights reserved.