N-(4-(4-((oxiran-2-ylmethyl)sulfonyl)phenoxy)phenyl)acetamide | 869577-59-3

• 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: N-(4-(4-((oxiran-2-ylmethyl)sulfonyl)phenoxy)phenyl)acetamide
• 英文别名: [4-(4-acetamidophenoxy)phenylsulfonyl]methyloxirane；N-[4-[4-(oxiran-2-ylmethylsulfonyl)phenoxy]phenyl]acetamide
• CAS: 869577-59-3
• 化学式: C₁₇H₁₇NO₅S
• 分子量: 347.392
• InChiKey: OWTOMCNNYCIQFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-(4-((oxiran-2-ylmethyl)sulfonyl)phenoxy)phenyl)acetamide 在 硫脲 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以89.6%的产率得到ND-364
  参考文献：
  名称：

  Synthesis of chiral ND-322, ND-364 and ND-364 derivatives as selective inhibitors of human gelatinase

  摘要：

  Compounds 10 (ND-322) and 15 (ND-364) are potent selective inhibitors for gelatinases, matrix metalloproteinase 2 (MMP2) and matrix metalloproteinase 9 (MMP9). However, both of them are racemates. Herein we report facile synthesis of optically active (R)- and (S)-enantiomers of compounds 10 and 15. And the sulfonyl of 15 was transformed to sulfinyl to obtain four epimeric mixtures. All synthesized thiirane-based compounds were evaluated in MMP2 and MMP9 inhibitory assays. Our results indicated that the configuration of thiirane moiety had little effects on gelatinase inhibition, but the substitution of sulfinyl for sulfonyl was detrimental to gelatinase inhibition. Besides, all target compounds exhibited no inhibition against other two Zn2+ dependant metalloproteases, aminopeptidase N (APN) and histone deacetylases (HDACs), which confirmed the unique Zn2+ chelation mechanism of thiirane moiety against gelatinases. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.013
• 作为产物：
  描述：

  2-(((4-(4-nitrophenoxy)phenyl)thio)methyl)oxirane 在 titanium(IV) isopropylate 、 过氧化氢异丙苯 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.58h， 生成 N-(4-(4-((oxiran-2-ylmethyl)sulfonyl)phenoxy)phenyl)acetamide
  参考文献：
  名称：

  Synthesis of chiral ND-322, ND-364 and ND-364 derivatives as selective inhibitors of human gelatinase

  摘要：

  Compounds 10 (ND-322) and 15 (ND-364) are potent selective inhibitors for gelatinases, matrix metalloproteinase 2 (MMP2) and matrix metalloproteinase 9 (MMP9). However, both of them are racemates. Herein we report facile synthesis of optically active (R)- and (S)-enantiomers of compounds 10 and 15. And the sulfonyl of 15 was transformed to sulfinyl to obtain four epimeric mixtures. All synthesized thiirane-based compounds were evaluated in MMP2 and MMP9 inhibitory assays. Our results indicated that the configuration of thiirane moiety had little effects on gelatinase inhibition, but the substitution of sulfinyl for sulfonyl was detrimental to gelatinase inhibition. Besides, all target compounds exhibited no inhibition against other two Zn2+ dependant metalloproteases, aminopeptidase N (APN) and histone deacetylases (HDACs), which confirmed the unique Zn2+ chelation mechanism of thiirane moiety against gelatinases. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.013

文献信息

• Inhibitors of Matrix Metallaproteinases
  申请人：Lee Mijoon

  公开号：US20090005420A1

  公开（公告）日：2009-01-01

  The present invention provides novel compounds of formulas I-IX, as described herein. Also provided are compositions of compounds of formulas I-IX, methods of making compounds of formulas I-IX, and methods of using compounds of formulas I-IX. The compounds of the invention can be used to inhibit matrix metalloproteinases, and are useful to treat conditions and diseases associated therewith.

  本发明提供了式I-IX的新化合物，如本文所述。还提供了式I-IX化合物的组合物，制备式I-IX化合物的方法以及使用式I-IX化合物的方法。本发明中的化合物可用于抑制基质金属蛋白酶，并可用于治疗与之相关的疾病和症状。
• INHIBITORS OF MATRIX METALLOPROTEINASES
  申请人：Lee Mijoon

  公开号：US20110224275A1

  公开（公告）日：2011-09-15

  The present invention provides novel compounds of formulas I-IX, as described herein. Also provided are compositions of compounds of formulas I-IX, methods of making compounds of formulas I-IX, and methods of using compounds of formulas I-IX. The compounds of the invention can be used to inhibit matrix metalloproteinases, and are useful to treat conditions and diseases associated therewith.

  本发明提供了如公式I-IX所述的新化合物。还提供了公式I-IX化合物的组合物、制备公式I-IX化合物的方法以及使用公式I-IX化合物的方法。本发明的化合物可用于抑制基质金属蛋白酶，并可用于治疗与之相关的疾病和病症。
• US7928127B2
  申请人：——

  公开号：US7928127B2

  公开（公告）日：2011-04-19
• US8093287B2
  申请人：——

  公开号：US8093287B2

  公开（公告）日：2012-01-10
• [EN] INHIBITORS OF MATRIX METALLOPROTEINASES<br/>[FR] INHIBITEURS DE METALLOPROTEINASES MATRICIELLES
  申请人：LEE MIJOON

  公开号：WO2006125208A1

  公开（公告）日：2006-11-23

  [EN] The present invention provides novel compounds of formulas I-IX, as described herein. Also provided are compositions of compounds of formulas I-IX, methods of making compounds of formulas I-IX, and methods of using compounds of formulas I-IX. The compounds of the invention can be used to inhibit matrix metalloproteinases, and are useful to treat conditions and diseases associated therewith.
  [FR] L'invention concerne des nouveaux composés de formules I-IX. Elle concerne également des compositions de composés de formules I-IX, des procédés de fabrication de composés de formules I-IX, et des procédés d'utilisation de ces composés de formules I-IX. Les composés de l'invention peuvent être utilisés afin d'inhiber les métalloprotéinases matricielles, et sont utiles dans le traitement d'états et de maladies y étant associés.