(1S)-1-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-((4-(4'-(trifluoromethoxy)phenoxy)phenyl)sulfonyl)ethyl(hydroxy)formamide | 286845-00-9

• 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: (1S)-1-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-((4-(4'-(trifluoromethoxy)phenoxy)phenyl)sulfonyl)ethyl(hydroxy)formamide
• 英文别名: ABT-518；[S-(R*,R*)]-N-[1-(2,2-dimethyl-1,3-dioxol-4-yl)]-2-[[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonyl]ethyl-N-hydroxyformamide；[S-(R*,R*)]-N-[2,2-dimethyl-1,3-dioxol-4-yl]-2-({4-[4-(trifluoromethoxy)phenoxy]phenyl}sulfonyl)ethyl-N-hydroxyformamide；(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-({4-[4'-(trifluoromethoxy)phenoxy]phenyl}sulfonyl)ethyl(hydroxy)formamide；N-((S)-1-((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2-((4-(4-(trifluoromethoxy)phenoxy)phenyl)sulfonyl)ethyl)-N-hydroxyformamide；N-[(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonylethyl]-N-hydroxyformamide
• CAS: 286845-00-9
• 化学式: C₂₁H₂₂F₃NO₈S
• 分子量: 505.469
• InChiKey: IVPPTWCRAFCOFJ-RTBURBONSA-N

物化性质

• 沸点：
  606.1±65.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (4S)-2,2-dimethyl-4-((E/Z)-2-(4-(4-trifluoromethoxyphenoxy)phenylsulfonyl)ethenyl)-[1,3]dioxolane 在 羟胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 (1S)-1-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-((4-(4'-(trifluoromethoxy)phenoxy)phenyl)sulfonyl)ethyl(hydroxy)formamide
  参考文献：
  名称：

  Phenoxyphenyl Sulfone N-Formylhydroxylamines (Retrohydroxamates) as Potent, Selective, Orally Bioavailable Matrix Metalloproteinase Inhibitors

  摘要：

  A novel series of sulfone N-formylhydroxylamines (retrohydroxamates) have been investigated as matrix metalloproteinases (MMP) inhibitors. The substitution of the ether linkage of ABT-770 (5) with a sulfone group 13a led to a substantial increase in activity against MMP-9 but was accompanied by a loss of selectivity for inhibition of MMP-2 and -9 over MMP-1 and diminished oral exposure. Replacement of the biphenyl P1' substituent with a phenoxyphenyl group provided compounds that are highly selective for inhibition of MMP-2 and -9 over MMP-1. Optimization of the substituent adjacent to the retrohydroxamate center in this series led to the clinical candidate ABT-518 (6), a highly potent, selective, orally bioavailable MMP inhibitor that has been shown to significantly inhibit tumor growth in animal cancer models.

  DOI：

  10.1021/jm0103920

文献信息

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

  公开号：US06350902B2

  公开（公告）日：2002-02-26

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

  该瞬时发明提供了一种选择性N-甲酰化N-羟胺的方法。
• Compounds for treating inflammatory disorders, demyelinating disdorders and cancers
  申请人：Ajami M. Alfred

  公开号：US20080108641A1

  公开（公告）日：2008-05-08

  Compounds of formula (I) and a method of treating a patient suffering from an inflammatory and/or demyelinating disorders, comprising administering to said patient a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof. Definitions for the variables are provided therein.

  公式（I）的化合物及治疗患有炎症和/或脱髓鞘性疾病的患者的方法，包括向该患者施用公式（I）的化合物或其药学上可接受的盐的治疗有效量。其中提供了变量的定义。
• REVERSE HYDROXAMATE INHIBITORS OF MATRIX METALLOPROTEINASES
  申请人：ABBOTT LABORATORIES

  公开号：EP1147101B1

  公开（公告）日：2002-11-20
• Method of treating vascular disease at a bifurcated vessel using coated balloon
  申请人：Toner L. John

  公开号：US20070027523A1

  公开（公告）日：2007-02-01

  Disclosed is a method for delivery of at least one therapeutic agent from an angioplasty balloon for treating vascular disease at a bifurcated vessel. The invention also relates to the method of loading the beneficial agents onto the balloon and the device, as well as the method of delivery of the agents from separate surfaces. The invention also relates to a method of loading multiple beneficial agents onto the balloon surfaces
• Method of loading beneficial agent to a prosthesis by fluid-jet application
  申请人：Verlee Donald

  公开号：US20070053953A1

  公开（公告）日：2007-03-08

  An interventional device for delivery of beneficial agent to a lumen and methods of loading and manufacture of the same, which include a prosthesis loaded with beneficial agent to provide a controlled dosage concentration of beneficial agent to the lumen. The beneficial agent is loaded onto the prosthesis by a fluid-dispenser having a dispensing element capable of dispensing the beneficial agent in discrete droplets, each droplet having a controlled trajectory. The method of loading beneficial agent includes dispensing beneficial agent in a raster format and/or an off-axis format along a dispensing path.