5-(3-aminomethylphenyl)furan-2-carboxylic acid ((S)-cyclohexylmethylcarbamoylmethyl)amide | 1227193-49-8

• 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-(3-aminomethylphenyl)furan-2-carboxylic acid ((S)-cyclohexylmethylcarbamoylmethyl)amide
• 英文别名: 5-(3-aminomethyl-phenyl)-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide；5-[3-(aminomethyl)phenyl]-N-[(1S)-1-cyclohexyl-2-(methylamino)-2-oxoethyl]furan-2-carboxamide
• CAS: 1227193-49-8
• 化学式: C₂₁H₂₇N₃O₃
• 分子量: 369.464
• InChiKey: ITNSZHIYMNQNNR-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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-(3-aminomethylphenyl)furan-2-carboxylic acid ((S)-cyclohexylmethylcarbamoylmethyl)amide 、 6-(三氟甲基)吡啶-2-甲酸 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 N-[3-(5-{[(1S)-1-cyclohexyl-2-(methylamino)-2-oxoethyl]carbamoyl}furan-2-yl)benzyl]-6-(trifluoromethyl)pyridine-2-carboxamide
  参考文献：
  名称：

  SAR studies of non-zinc-chelating MMP-13 inhibitors: Improving selectivity and metabolic stability

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.07.036
• 作为产物：
  描述：

  (3-{5-[((S)-cyclohexylmethylcarbamoylmethyl)carbamoyl]furan-2-yl}benzyl)carbamic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 5-(3-aminomethylphenyl)furan-2-carboxylic acid ((S)-cyclohexylmethylcarbamoylmethyl)amide
  参考文献：
  名称：

  SAR studies of non-zinc-chelating MMP-13 inhibitors: Improving selectivity and metabolic stability

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.07.036

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：Farrow Neil Alexander

  公开号：US08637550B2

  公开（公告）日：2014-01-28

  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式(I)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
• 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