Ethyl 4-[4-(1,3-benzodioxol-5-yloxy)phenyl]sulfonylpiperidine-4-carboxylate;hydrochloride | 226401-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 4-[4-(1,3-benzodioxol-5-yloxy)phenyl]sulfonylpiperidine-4-carboxylate;hydrochloride
• CAS: 226401-02-1
• 化学式: C₂₁H₂₃NO₇S*ClH
• 分子量: 469.943
• InChiKey: DUPNTOUYPPASFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-乙氧基-1-三甲硅氧基环丙烷 、 Ethyl 4-[4-(1,3-benzodioxol-5-yloxy)phenyl]sulfonylpiperidine-4-carboxylate;hydrochloride 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以100%的产率得到Ethyl 4-[4-(1,3-benzodioxol-5-yloxy)phenyl]sulfonyl-1-cyclopropylpiperidine-4-carboxylate
  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：

  1-O-tert-butyl 4-O-ethyl 4-[4-(1,3-benzodioxol-5-yloxy)phenyl]sulfonylpiperidine-1,4-dicarboxylate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.67h， 以92%的产率得到Ethyl 4-[4-(1,3-benzodioxol-5-yloxy)phenyl]sulfonylpiperidine-4-carboxylate;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