Ethyl 1-methyl-4-(4-phenylsulfanylphenyl)sulfonylpiperidine-4-carboxylate | 226397-44-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Ethyl 1-methyl-4-(4-phenylsulfanylphenyl)sulfonylpiperidine-4-carboxylate
• CAS: 226397-44-0
• 化学式: C₂₁H₂₅NO₄S₂
• 分子量: 419.566
• InChiKey: AKUFUTOJXJJJBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 1-methyl-4-(4-phenylsulfanylphenyl)sulfonylpiperidine-4-carboxylate 在 N-甲基吗啉 、 甲醇 、 氢氧化钾 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 乙酰氯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 87.0h， 生成 N-hydroxy-1-methyl-4-(4-phenylsulfanylphenyl)sulfonylpiperidine-4-carboxamide;hydrochloride
  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 盐酸 、 吡啶硼烷 、 potassium carbonate 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 97.5h， 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