(1R,5S)-2-(4-hydroxyphenyl)sulfonyl-6-oxa-2-azabicyclo[3.2.1]octan-7-one | 448963-99-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,5S)-2-(4-hydroxyphenyl)sulfonyl-6-oxa-2-azabicyclo[3.2.1]octan-7-one
• CAS: 448963-99-3
• 化学式: C₁₂H₁₃NO₅S
• 分子量: 283.305
• InChiKey: GZXQBWSYIXLGDW-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,5S)-2-(4-hydroxyphenyl)sulfonyl-6-oxa-2-azabicyclo[3.2.1]octan-7-one 在 羟胺 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,4S)-N,4-dihydroxy-1-[4-[(2-methylphenyl)methoxy]phenyl]sulfonylpiperidine-2-carboxamide
  参考文献：
  名称：

  Synthesis and biological activity of selective pipecolic acid-based TNF-α converting enzyme (TACE) inhibitors

  摘要：

  A series of novel, selective TNF-alpha converting enzyme inhibitors based on 4-hydroxy and 5-hydroxy pipecolate hydroxamic acid scaffolds is described. The potency and selectivity of TACE inhibition is dramatically influenced by the nature of the sulfonamide group which interacts with the S1' site of the enzyme, Substituted 4-benzyloxybenzenesulfonamides exhibit excellent TACE potency with > 100x selectivity over inhibition of matrix metalloprotease-1 (MMP-1). Alkyl substituents on the ortho position of the benzyl ether moiety give the most potent inhibition of TNF-alpha release in LPS-treated human whole blood. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00183-x
• 作为产物：
  描述：

  4-(苄氧基)苯-1-磺酰氯 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,5S)-2-(4-hydroxyphenyl)sulfonyl-6-oxa-2-azabicyclo[3.2.1]octan-7-one
  参考文献：
  名称：

  Synthesis and biological activity of selective pipecolic acid-based TNF-α converting enzyme (TACE) inhibitors

  摘要：

  A series of novel, selective TNF-alpha converting enzyme inhibitors based on 4-hydroxy and 5-hydroxy pipecolate hydroxamic acid scaffolds is described. The potency and selectivity of TACE inhibition is dramatically influenced by the nature of the sulfonamide group which interacts with the S1' site of the enzyme, Substituted 4-benzyloxybenzenesulfonamides exhibit excellent TACE potency with > 100x selectivity over inhibition of matrix metalloprotease-1 (MMP-1). Alkyl substituents on the ortho position of the benzyl ether moiety give the most potent inhibition of TNF-alpha release in LPS-treated human whole blood. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00183-x