4-(4-but-2-ynyloxy-benzenesulfonylmethyl)-piperidine-1,4-dicarboxylic acid ethyl ester methyl ester | 287202-33-9

• 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-ynyloxy-benzenesulfonylmethyl)-piperidine-1,4-dicarboxylic acid ethyl ester methyl ester
• CAS: 287202-33-9
• 化学式: C₂₁H₂₇NO₇S
• 分子量: 437.514
• InChiKey: WGBWVWFHYHLHDO-UHFFFAOYSA-N

物化性质

• 沸点：
  602.2±55.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  99.21
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-(4-but-2-ynyloxy-benzenesulfonylmethyl)-piperidine-1,4-dicarboxylic acid ethyl ester methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.08h， 生成 4-(4-But-2-ynyloxy-benzenesulfonylmethyl)-piperidine-1,4-dicarboxylic acid monomethyl ester
  参考文献：
  名称：

  Design and synthesis of 3,3-piperidine hydroxamate analogs as selective TACE inhibitors

  摘要：

  Structure-based methods were used to design P-sulfone 3,3-piperidine hydroxamates as TACE inhibitors with the aim of improving selectivity for TACE versus MMP-13. Several compounds in this series were synthesized and evaluated in enzymatic and cell-based assays. These analogs exhibit excellent in vitro potency against isolated TACE enzyme and show good selectivity for TACE over the related metalloproteases MMP-2, -13, and -14. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.022
• 作为产物：
  描述：

  4-(4-Hydroxy-phenylsulfanylmethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester 在 TEA 、 caesium carbonate 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 4-(4-but-2-ynyloxy-benzenesulfonylmethyl)-piperidine-1,4-dicarboxylic acid ethyl ester methyl ester
  参考文献：
  名称：

  Design and synthesis of 3,3-piperidine hydroxamate analogs as selective TACE inhibitors

  摘要：

  Structure-based methods were used to design P-sulfone 3,3-piperidine hydroxamates as TACE inhibitors with the aim of improving selectivity for TACE versus MMP-13. Several compounds in this series were synthesized and evaluated in enzymatic and cell-based assays. These analogs exhibit excellent in vitro potency against isolated TACE enzyme and show good selectivity for TACE over the related metalloproteases MMP-2, -13, and -14. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.022

文献信息

• ALKYNYL CONTAINING HYDROXAMIC ACID DERIVATIVES, THEIR PREPARATION AND THEIR USE AS MATRIX METALLOPROTEINASE (MMP) INHIBITORS / TNF-ALPHA CONVERTING ENZYME (TACE) INHIBITORS
  申请人：Wyeth Holdings Corporation

  公开号：EP1147085B1

  公开（公告）日：2005-11-16