1-(2-Methoxyethyl)-4-[4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]sulfonylpiperidine-4-carboxylic acid | 226400-95-9

• 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: 1-(2-Methoxyethyl)-4-[4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]sulfonylpiperidine-4-carboxylic acid
• CAS: 226400-95-9
• 化学式: C₂₂H₂₄F₃NO₆S₂
• 分子量: 519.563
• InChiKey: QFWJYISBTNSQEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  O-(四氢-2H-吡喃-2-基)羟基胺 、 1-(2-Methoxyethyl)-4-[4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]sulfonylpiperidine-4-carboxylic acid 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以69.8%的产率得到1-(2-methoxyethyl)-N-(oxan-2-yloxy)-4-[4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]sulfonylpiperidine-4-carboxamide
  参考文献：
  名称：

  Orally Active MMP-1 Sparing α-Tetrahydropyranyl and α-Piperidinyl Sulfone Matrix Metalloproteinase (MMP) Inhibitors with Efficacy in Cancer, Arthritis, and Cardiovascular Disease

  摘要：

  alpha-Sulfone-alpha-piperidine and alpha-tetrahydropyranyl hydroxamates were explored that are potent inhibitors of MMP's-2, -9, and -13 that spare MMP-1, with oral efficacy in inhibiting tumor growth in mice and left-ventricular hypertrophy in rats and in the bovine cartilage degradation ex vivo explant system. alpha-Piperidine 19v (SC-78080/SD-2590) was selected for development toward the initial indication of cancer, while alpha-piperidine and alpha-tetrahydropyranyl hydroxamates 19w (SC-77964) and 9l (SC-77774), respectively, were identified as backup compounds.

  DOI：

  10.1021/jm100669j
• 作为产物：
  描述：

  Ethyl 1-(2-methoxyethyl)-4-[4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]sulfonylpiperidine-4-carboxylate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以100%的产率得到1-(2-Methoxyethyl)-4-[4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]sulfonylpiperidine-4-carboxylic acid
  参考文献：
  名称：

  Orally Active MMP-1 Sparing α-Tetrahydropyranyl and α-Piperidinyl Sulfone Matrix Metalloproteinase (MMP) Inhibitors with Efficacy in Cancer, Arthritis, and Cardiovascular Disease

  摘要：

  alpha-Sulfone-alpha-piperidine and alpha-tetrahydropyranyl hydroxamates were explored that are potent inhibitors of MMP's-2, -9, and -13 that spare MMP-1, with oral efficacy in inhibiting tumor growth in mice and left-ventricular hypertrophy in rats and in the bovine cartilage degradation ex vivo explant system. alpha-Piperidine 19v (SC-78080/SD-2590) was selected for development toward the initial indication of cancer, while alpha-piperidine and alpha-tetrahydropyranyl hydroxamates 19w (SC-77964) and 9l (SC-77774), respectively, were identified as backup compounds.

  DOI：

  10.1021/jm100669j

文献信息

• Orally Active MMP-1 Sparing α-Tetrahydropyranyl and α-Piperidinyl Sulfone Matrix Metalloproteinase (MMP) Inhibitors with Efficacy in Cancer, Arthritis, and Cardiovascular Disease
  作者：Daniel P. Becker、Thomas E. Barta、Louis J. Bedell、Terri L. Boehm、Brian R. Bond、Jeffery Carroll、Chris P. Carron、Gary A. DeCrescenzo、Alan M. Easton、John N. Freskos、Chris L. Funckes-Shippy、Marcia Heron、Susan Hockerman、Carol Pearcy Howard、James R. Kiefer、Madeleine H. Li、Karl J. Mathis、Joseph J. McDonald、Pramod P. Mehta、Grace E. Munie、Teresa Sunyer、Craig A. Swearingen、Clara I. Villamil、Dean Welsch、Jennifer M. Williams、Ying Yu、Jun Yao

  DOI：10.1021/jm100669j

  日期：2010.9.23

  alpha-Sulfone-alpha-piperidine and alpha-tetrahydropyranyl hydroxamates were explored that are potent inhibitors of MMP's-2, -9, and -13 that spare MMP-1, with oral efficacy in inhibiting tumor growth in mice and left-ventricular hypertrophy in rats and in the bovine cartilage degradation ex vivo explant system. alpha-Piperidine 19v (SC-78080/SD-2590) was selected for development toward the initial indication of cancer, while alpha-piperidine and alpha-tetrahydropyranyl hydroxamates 19w (SC-77964) and 9l (SC-77774), respectively, were identified as backup compounds.