N-(oxan-2-yloxy)-4-[4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]sulfonyloxane-4-carboxamide | 226399-36-6

• 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-(oxan-2-yloxy)-4-[4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]sulfonyloxane-4-carboxamide
• CAS: 226399-36-6
• 化学式: C₂₄H₂₆F₃NO₇S₂
• 分子量: 561.6
• InChiKey: VDDPHJBWLDXGFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-(oxan-2-yloxy)-4-[4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]sulfonyloxane-4-carboxamide 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 18.0h， 以24%的产率得到N-hydroxy-4-{[4-(4-[(trifluoromethyl)thio]phenoxy)phenyl]sulfonyl}tetrahydro-2H-pyran-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：

  4-[(4-fluorophenyl)sulfonyl]tetrahydro-N-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-pyran-4-carboxamide 、 4-(三氟甲硫基)苯酚 在 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 生成 N-(oxan-2-yloxy)-4-[4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]sulfonyloxane-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