(1R,3S,5S)-3-[4-(4-Fluoro-phenoxy)-benzenesulfonylamino]-8-oxa-bicyclo[3.2.1]octane-3-carboxylic acid tert-butyl ester | 815576-04-6

• 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: (1R,3S,5S)-3-[4-(4-Fluoro-phenoxy)-benzenesulfonylamino]-8-oxa-bicyclo[3.2.1]octane-3-carboxylic acid tert-butyl ester
• CAS: 815576-04-6
• 化学式: C₂₄H₂₈FNO₆S
• 分子量: 477.554
• InChiKey: AOESDVCMMUZCFW-IRJINJETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,3S,5S)-3-[4-(4-Fluoro-phenoxy)-benzenesulfonylamino]-8-oxa-bicyclo[3.2.1]octane-3-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到3-exo-[4-(4-Fluorophenoxy)benzenesulfonylamino]-8-oxabicyclo[3.2.1]octane-3-carboxylic acid
  参考文献：
  名称：

  Pyran-containing sulfonamide hydroxamic acids: potent MMP inhibitors that spare MMP-1

  摘要：

  The SAR of a series of sterically hindered sulfonamide hydroxamic acids with relatively large P-1' groups is described. The compounds typically spare MMP-1 while being potent inhibitors of MMP-13. The metabolically more stable compounds in the series contain either a monocyclic or bicyclic pyran ring adjacent to the hydroxamate group. Despite the sparing of MMP-1, preclinical and clinical studies revealed that fibrosis in rats and NISS in humans is still produced. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.083
• 作为产物：
  描述：

  ((2R,5S)-tetrahydrofuran-2,5-diyl)bis(methylene) bis(4-methylbenzenesulfonate) 在 4-二甲氨基吡啶 、 盐酸羟胺 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,3S,5S)-3-[4-(4-Fluoro-phenoxy)-benzenesulfonylamino]-8-oxa-bicyclo[3.2.1]octane-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Pyran-containing sulfonamide hydroxamic acids: potent MMP inhibitors that spare MMP-1

  摘要：

  The SAR of a series of sterically hindered sulfonamide hydroxamic acids with relatively large P-1' groups is described. The compounds typically spare MMP-1 while being potent inhibitors of MMP-13. The metabolically more stable compounds in the series contain either a monocyclic or bicyclic pyran ring adjacent to the hydroxamate group. Despite the sparing of MMP-1, preclinical and clinical studies revealed that fibrosis in rats and NISS in humans is still produced. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.083