4-{[4-(2-butynyloxy)-phenyl]sulfonyl}-1,4-diazepane-5-carboxylic acid | 287408-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-{[4-(2-butynyloxy)-phenyl]sulfonyl}-1,4-diazepane-5-carboxylic acid
• 英文别名: 4-(4-But-2-ynoxyphenyl)sulfonyl-1,4-diazepane-5-carboxylic acid
• CAS: 287408-81-5
• 化学式: C₁₆H₂₀N₂O₅S
• 分子量: 352.411
• InChiKey: HQFRIPIOEUSXDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-{[4-(2-butynyloxy)-phenyl]sulfonyl}-1,4-diazepane-5-carboxylic acid 在 盐酸 、 sodium hydroxide 、 羟胺 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-{[4-(2-Butynyloxy)phenyl]sulfonyl}-N-hydroxy-1,4-diazepane-5-carboxamide
  参考文献：
  名称：

  Synthesis and SAR of diazepine and thiazepine TACE and MMP inhibitors

  摘要：

  Potent and selective TACE and MMP inhibitors utilizing the diazepine and thiazepine ring systems were synthesized and evaluated for biological activity in in vitro and in vivo models of TNF-α release. Oral activity in the mouse LPS model of TNF-α release was seen. Efficacy in the mouse collagen induced arthritis model was achieved with diazepine 20. © 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.053
• 作为产物：
  描述：

  [1,4]二氮杂烷-5-羧酸叔丁酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 4-{[4-(2-butynyloxy)-phenyl]sulfonyl}-1,4-diazepane-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and SAR of diazepine and thiazepine TACE and MMP inhibitors

  摘要：

  Potent and selective TACE and MMP inhibitors utilizing the diazepine and thiazepine ring systems were synthesized and evaluated for biological activity in in vitro and in vivo models of TNF-α release. Oral activity in the mouse LPS model of TNF-α release was seen. Efficacy in the mouse collagen induced arthritis model was achieved with diazepine 20. © 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.053

文献信息

• Acetylenic alpha -amino acid-based sulfonamide hydroxamic acid tace inhibitors
  申请人：——

  公开号：US20030008849A1

  公开（公告）日：2003-01-09

  Compounds of the formula: 1 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.

  公式为1的化合物可用于治疗由TNF-&agr;介导的疾病条件，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、克罗恩病和退行性软骨丢失。
• Acetylenic alpha-amino acid-based sulfonamide hydroxamic acid tace inhibitors
  申请人：Levin I. Jeremy

  公开号：US20050113346A1

  公开（公告）日：2005-05-26

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

  式为的化合物在治疗由TNF-α介导的疾病条件方面非常有用，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、克罗恩病和退行性软骨损失。
• ACETYLENIC ALPHA-AMINO ACID-BASED SULFONAMIDE HYDROXAMIC ACID TACE INHIBITORS
  申请人：Wyeth Holdings Corporation

  公开号：EP1144368B1

  公开（公告）日：2004-07-14
• US6225311B1
  申请人：——

  公开号：US6225311B1

  公开（公告）日：2001-05-01
• US6716833B2
  申请人：——

  公开号：US6716833B2

  公开（公告）日：2004-04-06