1-(2-methoxyethyl)-N-(oxan-2-yloxy)-4-[4-(4-propan-2-yloxyphenoxy)phenyl]sulfonylpiperidine-4-carboxamide | 226401-66-7

• 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)-N-(oxan-2-yloxy)-4-[4-(4-propan-2-yloxyphenoxy)phenyl]sulfonylpiperidine-4-carboxamide
• CAS: 226401-66-7
• 化学式: C₂₉H₄₀N₂O₈S
• 分子量: 576.711
• InChiKey: VKBUWIRCCFNJJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2-methoxyethyl)-N-(oxan-2-yloxy)-4-[4-(4-propan-2-yloxyphenoxy)phenyl]sulfonylpiperidine-4-carboxamide 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 以56%的产率得到N-hydroxy-4-{[4-(4-isopropoxyphenoxy)phenyl]sulfonyl}-1-(2-methoxyethyl)piperidine-4-carboxamide hydrochloride
  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：

  O-(四氢-2H-吡喃-2-基)羟基胺 、 1-(2-Methoxyethyl)-4-[4-(4-propan-2-yloxyphenoxy)phenyl]sulfonylpiperidine-4-carboxylic acid 在 N-甲基吗啉 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以63%的产率得到1-(2-methoxyethyl)-N-(oxan-2-yloxy)-4-[4-(4-propan-2-yloxyphenoxy)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