5-methyl-2-(3-methylbut-2-enyl)-2-(toluene-4-sulfonyl)hex-4-enoic acid ethyl ester | 212769-68-1

• 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: 5-methyl-2-(3-methylbut-2-enyl)-2-(toluene-4-sulfonyl)hex-4-enoic acid ethyl ester
• 英文别名: 5-methyl-2-(3-methylbut-2-enyl)-2-(p-toluenesulfonyl)hex-4-enoic acide ethyl ester；Ethyl 5-methyl-2-(3-methylbut-2-enyl)-2-(4-methylphenyl)sulfonylhex-4-enoate
• CAS: 212769-68-1
• 化学式: C₂₁H₃₀O₄S
• 分子量: 378.533
• InChiKey: VIKWZSNGLQSSJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  5-methyl-2-(3-methylbut-2-enyl)-2-(toluene-4-sulfonyl)hex-4-enoic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5-methyl-2-(3-methyl-but-2-enyl)-2-(toluene-4-sulfonyl)-hex-4-enoic acid
  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：

  4-甲基-(苯基磺酰基)乙酸乙酯 、 1-溴-3-甲基-2-丁烯 在 18-冠醚-6 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 以4.6 g的产率得到5-methyl-2-(3-methylbut-2-enyl)-2-(toluene-4-sulfonyl)hex-4-enoic 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

• N-HYDROXY-2-(ALKYL, ARYL, OR HETEROARYL SULFANYL, SULFINYL OR SULFONYL)-3-SUBSTITUTED ALKYL, ARYL OR HETEROARYLAMIDES AS MATRIX METALLOPROTEINASE INHIBITORS
  申请人：Wyeth Holdings Corporation

  公开号：EP0970046B1

  公开（公告）日：2003-12-10
• 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.