4-[4-(but-2-ynylamino)benzenesulfonylmethyl]piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester | 946857-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-[4-(but-2-ynylamino)benzenesulfonylmethyl]piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester
• CAS: 946857-30-3
• 化学式: C₂₄H₃₄N₂O₆S
• 分子量: 478.61
• InChiKey: GZIBLTHVHGKBPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  102.01
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-[4-(but-2-ynylamino)benzenesulfonylmethyl]piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Structure-based design of TACE selective inhibitors: Manipulations in the S1′–S3′ pocket

  摘要：

  A series of beta-sulfonyl hydroxamate TACE inhibitors, bearing a butynylamino or a butynyloxy Pl' group, was designed and synthesized. Of the compounds investigated, 22 has excellent potency against isolated TACE enzyme, shows good selectivity over MMP-2 and MMP- 13, and oral activity in an in vivo mouse model of TNF-alpha( production. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.031
• 作为产物：
  描述：

  4-(4-aminobenzenesulfonylmethyl)piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester 、 1-溴-2-丁炔 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.83h， 以63%的产率得到4-[4-(but-2-ynylamino)benzenesulfonylmethyl]piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester
  参考文献：
  名称：

  Structure-based design of TACE selective inhibitors: Manipulations in the S1′–S3′ pocket

  摘要：

  A series of beta-sulfonyl hydroxamate TACE inhibitors, bearing a butynylamino or a butynyloxy Pl' group, was designed and synthesized. Of the compounds investigated, 22 has excellent potency against isolated TACE enzyme, shows good selectivity over MMP-2 and MMP- 13, and oral activity in an in vivo mouse model of TNF-alpha( production. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.031