4-Methoxy-N-(2-morpholin-4-yl-ethyl)-benzenesulfonamide | 346715-27-3

• 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: 4-Methoxy-N-(2-morpholin-4-yl-ethyl)-benzenesulfonamide
• 英文别名: 4-Methoxy-N-[2-(morpholin-4-YL)ethyl]benzene-1-sulfonamide；4-methoxy-N-(2-morpholin-4-ylethyl)benzenesulfonamide
• CAS: 346715-27-3
• 化学式: C₁₃H₂₀N₂O₄S
• mdl: MFCD01212769
• 分子量: 300.379
• InChiKey: DYCRTSVHYPCSML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  76.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-Methoxy-N-(2-morpholin-4-yl-ethyl)-benzenesulfonamide 在 盐酸羟胺 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 N-hydroxy-2-[[4-methoxybenzenesulfonyl](2-[4-morpholino]ethyl)amino]acetamide
  参考文献：
  名称：

  Discovery of CGS 27023A, a Non-Peptidic, Potent, and Orally Active Stromelysin Inhibitor That Blocks Cartilage Degradation in Rabbits

  摘要：

  Structure-activity relationships of a lead hydroxamic acid inhibitor of recombinant human stromelysin were systematically defined by taking advantage of a concise synthesis that allowed diverse functionality to be explored at each position in a template. An ex vivo rat model and an in vivo rabbit model of stromelysin-induced cartilage degradation were used to further optimize these analogs for oral activity and duration of action. The culmination of these modifications resulted in CGS 27023A, a potent, orally active stromelysin inhibitor that blocks the erosion of cartilage matrix.

  DOI：

  10.1021/jm960871c
• 作为产物：
  描述：

  N-(2-氨基乙基)吗啉 、 对甲氧基苯磺酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 生成 4-Methoxy-N-(2-morpholin-4-yl-ethyl)-benzenesulfonamide
  参考文献：
  名称：

  Discovery of CGS 27023A, a Non-Peptidic, Potent, and Orally Active Stromelysin Inhibitor That Blocks Cartilage Degradation in Rabbits

  摘要：

  Structure-activity relationships of a lead hydroxamic acid inhibitor of recombinant human stromelysin were systematically defined by taking advantage of a concise synthesis that allowed diverse functionality to be explored at each position in a template. An ex vivo rat model and an in vivo rabbit model of stromelysin-induced cartilage degradation were used to further optimize these analogs for oral activity and duration of action. The culmination of these modifications resulted in CGS 27023A, a potent, orally active stromelysin inhibitor that blocks the erosion of cartilage matrix.

  DOI：

  10.1021/jm960871c

文献信息

• Design and synthesis of procollagen C-proteinase inhibitors
  作者：Eric Turtle、Nicholas Chow、Charles Yang、Sergio Sosa、Udo Bauer、Mitch Brenner、David Solow-Cordero、Wen-Bin Ho

  DOI：10.1016/j.bmcl.2012.10.067

  日期：2012.12

  Non-peptidic inhibitors of procollagen C-proteinase (PCP) were designed from substrate leads. Compounds were optimized for potency and selectivity, with N-substituted aryl sulfonamide hydroxamates having the best combination of these properties. Compounds 89 and 60 have IC50 values of 10 and 80 nM, respectively, against PCP; excellent selectivity over MMP's 1, 2, and 9; and activity in cell-based collagen deposition assays. (C) 2012 Elsevier Ltd. All rights reserved.