(S)-N-(1-((4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)methyl)-2-((4'-(trifluoromethoxy)(1,1'-biphenyl)-4-yl)oxy)ethyl)-N-hydroxyformamide | 220614-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-(1-((4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)methyl)-2-((4'-(trifluoromethoxy)(1,1'-biphenyl)-4-yl)oxy)ethyl)-N-hydroxyformamide
• 英文别名: ABT-770；N-[(1S)-1-[(4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)methyl]]-2-[[[4-(trifluoromethoxy)[1,1-biphenyl]-4-yl]oxy]ethyl]-N-hydroxyformamide；(1S)-2-(4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)-1-(((4'-(trifluoromethoxy)(1,1'-biphenyl)-4-yl)oxy)methyl)ethyl-(n-hydroxy)formamide；(1S)-2-(4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)-1-(((4'-(trifluoromethoxy)(1,1'-biphenyl)-4-yl)oxy)methyl)ethyl(hydroxy)formamide；(S)-N-[1-[(4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)methyl]-2-[[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]oxy]ethyl]-N-hydroxyformamide；Unii-I8nwp25thf；N-[(2S)-1-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-3-[4-[4-(trifluoromethoxy)phenyl]phenoxy]propan-2-yl]-N-hydroxyformamide
• CAS: 220614-50-6
• 化学式: C₂₂H₂₂F₃N₃O₆
• 分子量: 481.428
• InChiKey: IIHFBHZWJNGWRC-INIZCTEOSA-N

物化性质

• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  对溴三氟甲氧基苯 在 palladium on activated charcoal (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 偶氮二甲酸二异丙酯 、 氢气 、 三溴化硼 、 sodium carbonate 、 potassium carbonate 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-N-(1-((4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)methyl)-2-((4'-(trifluoromethoxy)(1,1'-biphenyl)-4-yl)oxy)ethyl)-N-hydroxyformamide
  参考文献：
  名称：

  Discovery and characterization of the potent, selective and orally bioavailable MMP inhibitor ABT-770

  摘要：

  Modification of the biphenyl portion of MMP inhibitor 2a gave analogue 2i which is greater than 1000-fold selective against MMP-2 versus MMP-1. The stereospecific synthesis of both enantiomers of 2i was achieved beginning with (S)- or (R)-benzyl glycidyl ether. The (S)-enantiomer, 11 (ABT-770), is orally bioavailable and efficacious in an in vivo model of tumor growth. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00032-4

文献信息

• Process for the selective N-formylation of N-hydroxylamines
  申请人：——

  公开号：US20010031896A1

  公开（公告）日：2001-10-18

  The instant invention provides a process for the selective N-formylation of N-hydroxylamines.

  这项瞬时发明提供了一种选择性N-甲酰化N-羟胺的过程。
• 2,2,2-Trifluoroethyl Formate:  A Versatile and Selective Reagent for the Formylation of Alcohols, Amines, and <i>N</i>-Hydroxylamines
  作者：David R. Hill、Chi-Nung Hsiao、Ravi Kurukulasuriya、Steven J. Wittenberger

  DOI：10.1021/ol016976d

  日期：2002.1.1

  [reaction: see text] Treatment of a variety of alcohols, amines, and N-hydroxylamines with 2,2,2-trifluoroethyl formate gave the corresponding formylated adducts in high yields.

  [反应：见正文]用2,2,2-三氟乙基甲酸酯处理各种醇，胺和N-羟胺，可以高收率得到相应的甲酰化加合物。
• Process for the preparation of matrix metalloproteinase inhibitors
  申请人：——

  公开号：US20020019539A1

  公开（公告）日：2002-02-14

  The instant invention provides a process for the synthesis of matrix metalloproteinase inhibitors.

  本发明提供了一种合成基质金属蛋白酶抑制剂的过程。
• Synthesis of [14C]ABT-770, matrix metalloproteinase inhibitor (MMPI), labelled in the phenoxy ring
  作者：Shirish N. Raja

  DOI：10.1002/jlcr.727

  日期：2003.8

  The MMPI [14C]ABT-770 (1), N-[(1S)-1-[(4,4-Dimethyl-2,5-dioxo-1-imi-dazolidinyl)methyl]]-2-[[4′-(trifluoromethoxy)[1,1′-biphenyl]-4-yl]oxy]ethyl]-N-hydroxyformamide was synthesized in 8 steps using 4-bromophenol-UL-14C (10) as a starting material. The Carbon-14 label was introduced in one of the metabolically stable biphenyl rings. The key sequence of the synthesis was a three-step one-pot reaction in which the hydantoin moiety was introduced, the imine oxidized and further hydrolyzed to get the penultimate precursor to [14C]ABT-770 (1) in 56% yield. Copyright © 2003 John Wiley & Sons, Ltd.

  MMPI [14C]ABT-770 (1), N-[(1S)-1-[(4,4-二甲基-2,5-二氧代-1-咪唑啉基)甲基]]-2-[[4以4-溴苯酚-UL-14C (10)为起始原料，分8步合成'-(三氟甲氧基)[1,1'-联苯]-4-基]氧基]乙基]-N-羟基甲酰胺。 Carbon-14 标记被引入代谢稳定的联苯环之一中。合成的关键顺序是三步一锅反应，其中引入乙内酰脲部分，氧化亚胺并进一步水解，得到[14C]ABT-770 (1) 的倒数第二个前体，产率 56%。版权所有 © 2003 约翰·威利父子有限公司
• Reverse hydroxamate inhibitors of matrix metalloproteinases
  申请人：——

  公开号：US20020007060A1

  公开（公告）日：2002-01-17

  Compounds having the formula 1 are matrix metalloproteinase inhibitors. Also disclosed are matrix metalloproteinase-inhibiting compositions and methods of inhibiting matrix metalloproteinase in a mammal.

  具有公式1的化合物是基质金属蛋白酶抑制剂。还披露了基质金属蛋白酶抑制剂组合物和在哺乳动物中抑制基质金属蛋白酶的方法。