5-bromo-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide | 1191923-17-7

• 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-bromo-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide
• 英文别名: 5-bromofuran-2-carboxylic acid ((S)-cyclohexylmethylcarbamoylmethyl)amide；5-bromo-N-[(1S)-1-cyclohexyl-2-(methylamino)-2-oxoethyl]furan-2-carboxamide
• CAS: 1191923-17-7
• 化学式: C₁₄H₁₉BrN₂O₃
• 分子量: 343.22
• InChiKey: DMZHFCHDPVNSIO-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  71.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  5-溴-2-糠酸 、 (S)-2-氨基-2-环己基-N-甲基乙酰胺盐酸盐 在 O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate 、 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 16.0h， 以78%的产率得到5-bromo-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide
  参考文献：
  名称：

  [EN] FUSED HETEROARYL DIAMIDE COMPOUNDS USEFUL AS MMP-13 INHIBITORS
  [FR] COMPOSÉS DE DIAMIDE D'HÉTÉROARYLE FUSIONNÉS UTILISÉS COMME INHIBITEURS DE MMP-13

  摘要：

  本发明涉及一种公式I所描述的化合物和组合物，其为MMP-13的抑制剂。本发明还涉及使用和制备公式I化合物的方法。

  公开号：

  WO2010045190A1

文献信息

• Fused Heteroaryl Diamide Compounds Useful as MMP-13 Inhibitors
  申请人：Heim-Riether Alexander

  公开号：US20110269668A1

  公开（公告）日：2011-11-03

  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.

  本发明涉及一种化合物和组合物，其化学式如下所述，该化合物和组合物是MMP-13的抑制剂。本发明还涉及使用和制备化合物的方法。
• 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。
• Fused heteroaryl diamide compounds useful as MMP-13 inhibitors
  申请人：Boehringer Ingelheim International GmbH

  公开号：US08338367B2

  公开（公告）日：2012-12-25

  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.

  本文披露了一种化合物和组合物，其化学式如下所述，可作为MMP-13的抑制剂。还披露了使用和制备化合物的方法。
• [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
• SAR studies of non-zinc-chelating MMP-13 inhibitors: Improving selectivity and metabolic stability
  作者：Donghong Amy Gao、Zhaoming Xiong、Alexander Heim-Riether、Laura Amodeo、E. Michael August、Xianhua Cao、Leonard Ciccarelli、Brandon K. Collins、Kyle Harrington、Kathleen Haverty、Melissa Hill-Drzewi、Xiang Li、Shuang Liang、Steluta Mariana Margarit、Neil Moss、Nelamangala Nagaraja、John Proudfoot、Rene Roman、Sabine Schlyer、Lana Smith Keenan、Steven Taylor、Bernd Wellenzohn、Dieter Wiedenmayer、Jun Li、Neil A. Farrow

  DOI：10.1016/j.bmcl.2010.07.036

  日期：2010.9

  SAR studies to improve the selectivity and metabolic stability of a class of recently discovered MMP-13 inhibitors are reported. Improved selectivity was achieved by modifying interactions with the S1' pocket. Metabolic stability was improved through reduction of inhibitor lipophilicity. This translated into lower in vivo clearance for the preferred compound. (C) 2010 Elsevier Ltd. All rights reserved.