1-tert-butyl 4-ethyl 4-{[4-(phenylthio)phenyl]sulfonyl}piperidine-1,4-dicarboxylate | 226397-38-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-tert-butyl 4-ethyl 4-{[4-(phenylthio)phenyl]sulfonyl}piperidine-1,4-dicarboxylate
• 英文别名: 1-O-tert-butyl 4-O-ethyl 4-(4-phenylsulfanylphenyl)sulfonylpiperidine-1,4-dicarboxylate
• CAS: 226397-38-2
• 化学式: C₂₅H₃₁NO₆S₂
• 分子量: 505.656
• InChiKey: NRRXFKBIXVRCFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-tert-butyl 4-ethyl 4-{[4-(phenylthio)phenyl]sulfonyl}piperidine-1,4-dicarboxylate 在 盐酸 、 吡啶硼烷 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 Ethyl 1-methyl-4-(4-phenylsulfanylphenyl)sulfonylpiperidine-4-carboxylate
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of β- and α-Piperidine Sulfone Hydroxamic Acid Matrix Metalloproteinase Inhibitors with Oral Antitumor Efficacy

  摘要：

  alpha-Piperidine-beta-sulfone hydroxamate derivatives were explored that are potent for matrix metalloproteinases (MMP)-2, -9, and -13 and are sparing of MMP-1. The investigation of the beta-sulfones subsequently led to the discovery of hitherto unknown alpha-sulfone hydroxamates that are superior to the corresponding beta-sulfones in potency for target MMPs, selectivity vs MMP-1, and exposure when dosed orally. alpha-Tiperidine-alpha-sulfone, hydroxamate 35f (SC-276) was advanced through antitumor and antiangiogenesis assays and was selected for development. Compound 35f demonstrates excellent antitumor activity vs MX-1 breast tumor in mice when dosed orally as monotherapy or in combination with paclitaxel.

  DOI：

  10.1021/jm0500875
• 作为产物：
  描述：

  N-Boc-4-哌啶甲酸乙酯 在 potassium carbonate 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.5h， 生成 1-tert-butyl 4-ethyl 4-{[4-(phenylthio)phenyl]sulfonyl}piperidine-1,4-dicarboxylate
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of β- and α-Piperidine Sulfone Hydroxamic Acid Matrix Metalloproteinase Inhibitors with Oral Antitumor Efficacy

  摘要：

  alpha-Piperidine-beta-sulfone hydroxamate derivatives were explored that are potent for matrix metalloproteinases (MMP)-2, -9, and -13 and are sparing of MMP-1. The investigation of the beta-sulfones subsequently led to the discovery of hitherto unknown alpha-sulfone hydroxamates that are superior to the corresponding beta-sulfones in potency for target MMPs, selectivity vs MMP-1, and exposure when dosed orally. alpha-Tiperidine-alpha-sulfone, hydroxamate 35f (SC-276) was advanced through antitumor and antiangiogenesis assays and was selected for development. Compound 35f demonstrates excellent antitumor activity vs MX-1 breast tumor in mice when dosed orally as monotherapy or in combination with paclitaxel.

  DOI：

  10.1021/jm0500875