ethyl (1-acetyl-4-piperidinyl){[4-(2-butynyloxy)phenyl]sulfonyl}acetate | 287393-52-6

• 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: ethyl (1-acetyl-4-piperidinyl){[4-(2-butynyloxy)phenyl]sulfonyl}acetate
• 英文别名: Ethyl(1-acetyl-4-piperidinyl){[4-(2-butynyloxy)phenyl]sulfonyl}acetate；ethyl 2-(1-acetylpiperidin-4-yl)-2-(4-but-2-ynoxyphenyl)sulfonylacetate
• CAS: 287393-52-6
• 化学式: C₂₁H₂₇NO₆S
• 分子量: 421.514
• InChiKey: LYKCOGSNRSDJBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (1-acetyl-4-piperidinyl){[4-(2-butynyloxy)phenyl]sulfonyl}acetate 以35%的产率得到(1-acetyl-4-piperidinyl){[4-(2-butynyloxy)phenyl]sulfonyl}acetic acid
  参考文献：
  名称：

  Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase and tace inhibitors

  摘要：

  该公式的化合物可用于治疗由TNF-α介导的疾病状况，例如类风湿性关节炎、骨关节炎、脓毒症、艾滋病、溃疡性结肠炎、多发性硬化症、克罗恩病和退化性软骨丧失。

  公开号：

  US06340691B1
• 作为产物：
  描述：

  4-but-2-ynyloxybenzenesulfonyl chloride 在 盐酸 、 calcium fluoride 、 potassium fluoride 、 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.5h， 生成 ethyl (1-acetyl-4-piperidinyl){[4-(2-butynyloxy)phenyl]sulfonyl}acetate
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 4-alkynyloxy Phenyl Sulfanyl, Sulfinyl, and Sulfonyl Alkyl Hydroxamates as Tumor Necrosis Factor-α Converting Enzyme and Matrix Metalloproteinase Inhibitors

  摘要：

  A series of 4-alkynyloxy phenyl sulfanyl, sulfinyl and sulfony alkyl and piperidine-4-carboxylic acid hydroxamides were synthesized. Their structure-activity relationships, against tumor necrosis factor-alpha (TACE) and matrix metalloproteinase (NIMP) inhibitor activities, are presented by investigating the oxidation state on sulfur and altering the P1' substituent. The sulfonyl derivatives 20-24 carrying a 4-butynyloxy moiety were selective TACE inhibitors over the MMPs tested. The sulfinyl derivatives showed a preference for a specific oxidation on sulfur as in compounds 25-28. The selectivity over MMPs was also demonstrated in the sulfonyl series. The enhanced cellular activity was achieved upon incorporating a butynyloxy substituent in the piperidene series. Compounds 64 and 65 were potent inhibitors of TNF-alpha release in the mouse at 100 mg/kg po.

  DOI：

  10.1021/jm040086x

文献信息

• Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase and TACE inhibitors
  申请人：Wyeth Holdings Corporation

  公开号：US06825354B2

  公开（公告）日：2004-11-30

  Compounds of the formula are useful in treating disease conditions mediated by TNF-&agr;, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.

  该式化合物在治疗由TNF-α介导的疾病条件中很有用，例如类风湿性关节炎，骨关节炎，败血症，艾滋病，溃疡性结肠炎，多发性硬化症，克隆病和退行性软骨损失。