2-methyl-2-(octane-1-sulfonyl)-3-phenylpropionic acid ethyl ester | 566899-82-9

• 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: 2-methyl-2-(octane-1-sulfonyl)-3-phenylpropionic acid ethyl ester
• 英文别名: Ethyl 2-methyl-2-octylsulfonyl-3-phenylpropanoate
• CAS: 566899-82-9
• 化学式: C₂₀H₃₂O₄S
• 分子量: 368.538
• InChiKey: HJONUUBHGZCZRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-2-(octane-1-sulfonyl)-3-phenylpropionic acid ethyl ester 在 sodium hydroxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 2-Methyl-2-(octane-1-sulfonyl)-3-phenyl-propionyl chloride
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of α-Sulfonylhydroxamic Acids as Novel, Orally Active Matrix Metalloproteinase Inhibitors for the Treatment of Osteoarthritis

  摘要：

  The matrix metalloproteinases (MMPs) are a family of zinc-containing endopeptidases that play a key role in both physiological and pathological tissue degradation. These enzymes are strictly regulated by endogenous inhibitors such as tissue inhibitors of MMPs and alpha(2)-macroglobulins. Overexpression of these enzymes has been implicated in various pathological disorders such as arthritis, tumor metastasis, cardiovascular diseases, and multiple sclerosis. Developing effective small-molecule inhibitors to modulate MMP activity is one approach to treat these degenerative diseases. The present work focuses on the discovery and SAR of novel N-hydroxy-alpha-phenylsulfonylacetamide derivatives, which are potent, selective, and orally active MMP inhibitors.

  DOI：

  10.1021/jm0205548
• 作为产物：
  描述：

  2-(octane-1-sulfanyl)propionic acid ethyl ester 在 18-冠醚-6 、 peroxodisulfate ion 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 生成 2-methyl-2-(octane-1-sulfonyl)-3-phenylpropionic acid ethyl ester
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of α-Sulfonylhydroxamic Acids as Novel, Orally Active Matrix Metalloproteinase Inhibitors for the Treatment of Osteoarthritis

  摘要：

  The matrix metalloproteinases (MMPs) are a family of zinc-containing endopeptidases that play a key role in both physiological and pathological tissue degradation. These enzymes are strictly regulated by endogenous inhibitors such as tissue inhibitors of MMPs and alpha(2)-macroglobulins. Overexpression of these enzymes has been implicated in various pathological disorders such as arthritis, tumor metastasis, cardiovascular diseases, and multiple sclerosis. Developing effective small-molecule inhibitors to modulate MMP activity is one approach to treat these degenerative diseases. The present work focuses on the discovery and SAR of novel N-hydroxy-alpha-phenylsulfonylacetamide derivatives, which are potent, selective, and orally active MMP inhibitors.

  DOI：

  10.1021/jm0205548

文献信息

• Synthesis and Structure−Activity Relationship of α-Sulfonylhydroxamic Acids as Novel, Orally Active Matrix Metalloproteinase Inhibitors for the Treatment of Osteoarthritis
  作者：Venkatesan Aranapakam、George T. Grosu、Jamie M. Davis、Baihua Hu、John Ellingboe、Jannie L. Baker、Jerauld S. Skotnicki、Arie Zask、John F. DiJoseph、Amy Sung、Michele A. Sharr、Loran M. Killar、Thomas Walter、Guixian Jin、Rebecca Cowling

  DOI：10.1021/jm0205548

  日期：2003.6.1

  The matrix metalloproteinases (MMPs) are a family of zinc-containing endopeptidases that play a key role in both physiological and pathological tissue degradation. These enzymes are strictly regulated by endogenous inhibitors such as tissue inhibitors of MMPs and alpha(2)-macroglobulins. Overexpression of these enzymes has been implicated in various pathological disorders such as arthritis, tumor metastasis, cardiovascular diseases, and multiple sclerosis. Developing effective small-molecule inhibitors to modulate MMP activity is one approach to treat these degenerative diseases. The present work focuses on the discovery and SAR of novel N-hydroxy-alpha-phenylsulfonylacetamide derivatives, which are potent, selective, and orally active MMP inhibitors.