N-[4-(4-chlorophenoxy)phenyl]methanesulfonamide | 890589-10-3

• 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-chlorophenoxy)phenyl]methanesulfonamide
• CAS: 890589-10-3
• 化学式: C₁₃H₁₂ClNO₃S
• 分子量: 297.762
• InChiKey: YGOFDNVCADVZHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[4-(4-chlorophenoxy)phenyl]methanesulfonamide 、 叔丁基二甲基甲硅烷基缩水甘油醚 在 potassium carbonate 、 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 、 四氢呋喃 为溶剂， 反应 0.5h， 以78%的产率得到N-[4-(4-chlorophenoxy)phenyl]-N-(2,3-dihydroxypropyl)methanesulfonamide
  参考文献：
  名称：

  Microwave assisted ring-opening of epoxides with N-biaryl sulfonamides in the synthesis of matrix metalloproteinase-9 inhibitors

  摘要：

  A microwave accelerated epoxide ring-opening process with N-biaryl sulfonamides is described. Under this mild, highly efficient condition, an alpha-hydroxy-beta-N-biaryl sulfonamide skeleton is rapidly assembled leading ultimately to a novel series of matrix metalloproteinase-9 inhibitors with single digit nanomolar activities. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.184
• 作为产物：
  描述：

  甲基磺酰氯 、 4'-氯-4-氨基二苯醚 在 吡啶 作用下， 反应 1.0h， 生成 N-[4-(4-chlorophenoxy)phenyl]methanesulfonamide
  参考文献：
  名称：

  β-N-Biaryl ether sulfonamide hydroxamates as potent gelatinase inhibitors: Part 2. Optimization of α-amino substituents

  摘要：

  The introduction and the optimization of an alpha-amino substituent based on a series of alpha-hydroxy-beta-N-biaryl ether sulfonamide hydroxamates is described. The modification leads to a new series of MMP-2/MMP-9 inhibitors with enhanced inhibitory activities and improved ADME properties. An efficacy study on reducing the ischemia-induced brain edema in the rat transient middle cerebral artery occlusion (tMCAo) model is also demonstrated. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.129

文献信息

• β-N-Biaryl ether sulfonamide hydroxamates as potent gelatinase inhibitors: Part 1. Design, synthesis, and lead identification
  作者：Shyh-Ming Yang、Robert H. Scannevin、Bingbing Wang、Sharon L. Burke、Lawrence J. Wilson、Prabha Karnachi、Kenneth J. Rhodes、Bharat Lagu、William V. Murray

  DOI：10.1016/j.bmcl.2007.11.119

  日期：2008.2

  A new series of beta-N-biaryl ether sulfonamide hydroxamates as novel gelatinase inhibitors is described. These compounds exhibit good potency for MMP-2 and MMP-9 without inhibiting MMP-1. The structure-activity relationships (SAR) reveal the biaryl ether type P1' moiety together with methanesulfonamide is the optimal combination that provides inhibitory activity of MMP-9 in the single-digit nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.
• β-N-Biaryl ether sulfonamide hydroxamates as potent gelatinase inhibitors: Part 2. Optimization of α-amino substituents
  作者：Shyh-Ming Yang、Robert H. Scannevin、Bingbing Wang、Sharon L. Burke、Zhihong Huang、Prabha Karnachi、Lawrence J. Wilson、Kenneth J. Rhodes、Bharat Lagu、William V. Murray

  DOI：10.1016/j.bmcl.2007.11.129

  日期：2008.2

  The introduction and the optimization of an alpha-amino substituent based on a series of alpha-hydroxy-beta-N-biaryl ether sulfonamide hydroxamates is described. The modification leads to a new series of MMP-2/MMP-9 inhibitors with enhanced inhibitory activities and improved ADME properties. An efficacy study on reducing the ischemia-induced brain edema in the rat transient middle cerebral artery occlusion (tMCAo) model is also demonstrated. (C) 2007 Elsevier Ltd. All rights reserved.
• Microwave assisted ring-opening of epoxides with N-biaryl sulfonamides in the synthesis of matrix metalloproteinase-9 inhibitors
  作者：Shyh-Ming Yang、William V. Murray

  DOI：10.1016/j.tetlet.2007.11.184

  日期：2008.1

  A microwave accelerated epoxide ring-opening process with N-biaryl sulfonamides is described. Under this mild, highly efficient condition, an alpha-hydroxy-beta-N-biaryl sulfonamide skeleton is rapidly assembled leading ultimately to a novel series of matrix metalloproteinase-9 inhibitors with single digit nanomolar activities. (C) 2007 Elsevier Ltd. All rights reserved.