4-[4-(1,3-benzodioxol-5-yloxy)phenyl]sulfonyl-N-(oxan-2-yloxy)-1-prop-2-ynylpiperidine-4-carboxamide | 226396-69-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[4-(1,3-benzodioxol-5-yloxy)phenyl]sulfonyl-N-(oxan-2-yloxy)-1-prop-2-ynylpiperidine-4-carboxamide
• CAS: 226396-69-6
• 化学式: C₂₇H₃₀N₂O₈S
• 分子量: 542.61
• InChiKey: HJFHUDZJYCZDIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  4-[4-(1,3-benzodioxol-5-yloxy)phenyl]sulfonyl-N-(oxan-2-yloxy)-1-prop-2-ynylpiperidine-4-carboxamide 在 甲醇 、 乙酰氯 作用下， 反应 3.0h， 以97%的产率得到4-{[4-(1,3-benzodioxol-5-yloxy)phenyl]sulfonyl}-N-hydroxy-1-prop-2-yn-1-ylpiperidine-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 、 4-[4-(1,3-Benzodioxol-5-yloxy)phenyl]sulfonyl-1-prop-2-ynylpiperidine-4-carboxylic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以2.86 g的产率得到4-[4-(1,3-benzodioxol-5-yloxy)phenyl]sulfonyl-N-(oxan-2-yloxy)-1-prop-2-ynylpiperidine-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