3-exo-[4-(4-Fluorophenoxy)benzenesulfonylamino]-8-oxabicyclo[3.2.1]octane-3-carboxylic acid | 246543-70-4

• 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: 3-exo-[4-(4-Fluorophenoxy)benzenesulfonylamino]-8-oxabicyclo[3.2.1]octane-3-carboxylic acid
• CAS: 246543-70-4
• 化学式: C₂₀H₂₀FNO₆S
• 分子量: 421.446
• InChiKey: SDQSEZLDVVHQRZ-XEMDLRDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  101.93
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-exo-[4-(4-Fluorophenoxy)benzenesulfonylamino]-8-oxabicyclo[3.2.1]octane-3-carboxylic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,3S,5R)-3-[4-(4-Fluoro-phenoxy)-benzenesulfonylamino]-8-oxa-bicyclo[3.2.1]octane-3-carbonyl chloride
  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 、 三氟乙酸 、 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 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

文献信息

• Bicyclic hydroxamic acid derivatives
  申请人：Pfizer Inc.

  公开号：US06110964A1

  公开（公告）日：2000-08-29

  A compound of the formula ##STR1## wherein Z and Q are as defined in the specification, to pharmaceutical compositions containing them and to their medicinal use.

  其中Z和Q如规范中定义的，用于含有它们的药物组合物及其药用的公式为##STR1##的化合物。
• BICYCLIC HYDROXAMIC ACID DERIVATIVES
  申请人：Pfizer Products Inc.

  公开号：EP1070069A1

  公开（公告）日：2001-01-24
• US6110964A
  申请人：——

  公开号：US6110964A

  公开（公告）日：2000-08-29
• [EN] BICYCLIC HYDROXAMIC ACID DERIVATIVES<br/>[FR] DERIVES BICYCLIQUES DE L'ACIDE HYDROXAMIQUE
  申请人：PFIZER PRODUCTS INC.

  公开号：WO1999052910A1

  公开（公告）日：1999-10-21

  (EN) A compound of formula (I), wherein Z and Q are as defined in the specification, to pharmaceutical compositions containing them and to their medicinal use.(FR) La présente invention concerne un composé de formule (I), dans laquelle Z et Q sont définis dans les spécifications, les compositions pharmaceutiques et les utilisations médicales associées.
• Pyran-containing sulfonamide hydroxamic acids: potent MMP inhibitors that spare MMP-1
  作者：Lawrence A. Reiter、Ralph P. Robinson、Kim F. McClure、Christopher S. Jones、Matthew R. Reese、Peter G. Mitchell、Ivan G. Otterness、Marcia L. Bliven、Jennifer Liras、Santo R. Cortina、Kathleen M. Donahue、James D. Eskra、Richard J. Griffiths、Mary E. Lame、Arturo Lopez-Anaya、Gary J. Martinelli、Shunda M. McGahee、Sue A. Yocum、Lori L. Lopresti-Morrow、Lisa M. Tobiassen、Marcie L. Vaughn-Bowser

  DOI：10.1016/j.bmcl.2004.04.083

  日期：2004.7

  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.