N-[(1S)-1-cyclohexyl-2-(methylamino)-2-oxoethyl]-5-[4-(methylsulfamoyl)phenyl]furan-2-carboxamide | 1191923-23-5

• 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: N-[(1S)-1-cyclohexyl-2-(methylamino)-2-oxoethyl]-5-[4-(methylsulfamoyl)phenyl]furan-2-carboxamide
• 英文别名: Furan-2-carboxamide deriv., 16
• CAS: 1191923-23-5
• 化学式: C₂₁H₂₇N₃O₅S
• 分子量: 433.528
• InChiKey: MUVBCBMUIYHNAG-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-bromo-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide 、 4-硼苯磺酰胺甲酯 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(1S)-1-cyclohexyl-2-(methylamino)-2-oxoethyl]-5-[4-(methylsulfamoyl)phenyl]furan-2-carboxamide
  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

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：WO2010056585A2

  公开（公告）日：2010-05-20

  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).
• 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.