1-(4-(三氟甲氧基)苯氧基)-4-(甲基磺酰基)苯 | 286844-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-(三氟甲氧基)苯氧基)-4-(甲基磺酰基)苯
• 英文名称: A-347058
• 英文别名: 4-(4'-trifluoromethoxyphenoxy)phenyl methyl sulfone；1-(methylsulfonyl)-4-(4'-(trifluoromethoxy)phenoxy)benzene；1-(4-(Trifluoromethoxy)phenoxy)-4-(methylsulfonyl)benzene；1-(4-methylsulfonylphenoxy)-4-(trifluoromethoxy)benzene
• CAS: 286844-91-5
• 化学式: C₁₄H₁₁F₃O₄S
• 分子量: 332.3
• InChiKey: PXTXILSHMIAKDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  1-(4-(三氟甲氧基)苯氧基)-4-(甲基磺酰基)苯 在 苯甲醛 作用下， 生成 (+/-)-N-hydroxy-N-[1-phenyl-2-[[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonyl]ethyl]formamide
  参考文献：
  名称：

  Reverse hydroxamate inhibitors of matrix metalloproteinases

  摘要：

  具有以下化学式的化合物是基质金属蛋白酶抑制剂。还公开了抑制基质金属蛋白酶的组合物和方法，用于在哺乳动物中抑制基质金属蛋白酶。

  公开号：

  US06294573B1
• 作为产物：
  描述：

  对三氟甲氧基苯酚 、 对氟苯甲砜 在 氢氧化钾 、 磷酸 作用下， 以 正庚烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 生成 1-(4-(三氟甲氧基)苯氧基)-4-(甲基磺酰基)苯
  参考文献：
  名称：

  Process for the preparation of matrix metalloproteinase inhibitors

  摘要：

  本发明公开了一种合成逆向羟肟酸酯基质金属蛋白酶（MMP）抑制剂的方法。

  公开号：

  US20020128496A1

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。
• Synthesis of [³H]ABT-518, a matrix metalloproteinase inhibitor (MMPI) labeled in the phenyl rings
  作者：Shirish N. Raja、Bruce W. Surber、Jia Du、Jeffrey L. Cross

  DOI：10.1002/jlcr.1574

  日期：2009.3

  A novel matrix metalloproteinase inhibitor, 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, was labeled with tritium in two phenyl rings in a seven-step synthesis. The overall radiochemical yield of [3H]ABT-518 in seven steps starting from 1-(methylsulfonyl)-4-[4-(trifluoromethoxy)phenoxy]benzene was 6.2% with the radiochemical purity of 99.4%. Copyright © 2009 John Wiley & Sons, Ltd.

  一种新型基质金属蛋白酶抑制剂，ABT-518，[S-(R*, R*)]-N-[1-(2, 2-二甲基-1,3-二氧杂环己烷-4-基)-2-[[4 -[4-(三氟甲氧基)-苯氧基]苯基]磺酰基]乙基]-N-羟基甲酰胺，通过七步合成在两个苯环上用氚标记。以1-(甲磺酰基)-4-[4-(三氟甲氧基)苯氧基]苯为原料，七步合成的[3H]ABT-518的总放化收率为6.2%，放化纯度为99.4%。版权所有 © 2009 约翰·威利父子有限公司
• [EN] REVERSE HYDROXAMATE INHIBITORS OF MATRIX METALLOPROTEINASES<br/>[FR] COMPOSES D'HYDROXAMATE INVERSE UTILISES COMME INHIBITEURS DE METALLOPROTEASES MATRICIELLES
  申请人：ABBOTT LAB

  公开号：WO2000044739A1

  公开（公告）日：2000-08-03

  Compounds having formula (I) are matric metalloproteinase inhibitors. Also disclosed are matrix metalloproteinase-inhibiting compositions and methods of inhibiting matrix metalloproteinase in a mammal.

  化学式为（I）的化合物是基质金属蛋白酶抑制剂。本发明还公开了基质金属蛋白酶抑制剂组合物以及在哺乳动物中抑制基质金属蛋白酶的方法。
• Phenoxyphenyl Sulfone <i>N</i>-Formylhydroxylamines (Retrohydroxamates) as Potent, Selective, Orally Bioavailable Matrix Metalloproteinase Inhibitors
  作者：Carol K. Wada、James H. Holms、Michael L. Curtin、Yujia Dai、Alan S. Florjancic、Robert B. Garland、Yan Guo、H. Robin Heyman、Jamie R. Stacey、Douglas H. Steinman、Daniel H. Albert、Jennifer J. Bouska、Ildiko N. Elmore、Carole L. Goodfellow、Patrick A. Marcotte、Paul Tapang、Douglas W. Morgan、Michael R. Michaelides、Steven K. Davidsen

  DOI：10.1021/jm0103920

  日期：2002.1.1

  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.
• The Development of a Large-Scale Synthesis of Matrix Metalloproteinase Inhibitor, ABT-518
  作者：Sou-Jen Chang、Dilinie Fernando、Michael Fickes、Ashok K. Gupta、David R. Hill、Todd McDermott、Shyamal Parekh、Zhenping Tian、Steven J. Wittenberger

  DOI：10.1021/op025525l

  日期：2002.5.1

  A process for the preparation of matrix metalloproteinase inhibitor ABT-518 has been developed. Significant improvements have been made to the first generation synthesis and are described here. The new process is very robust and efficient; multikilogram quantities of the title compound have been synthesized for clinical trials. ABT-518 was prepared by this six-step synthetic sequence in 51% overall yield with >99% ee.