1-Cyclopropyl-4-(4-fluorophenyl)sulfonylpiperidine-4-carboxylic acid | 476192-41-3

• 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: 1-Cyclopropyl-4-(4-fluorophenyl)sulfonylpiperidine-4-carboxylic acid
• CAS: 476192-41-3
• 化学式: C₁₅H₁₈FNO₄S
• 分子量: 327.377
• InChiKey: RSOOUXHNWKZLTH-UHFFFAOYSA-N

物化性质

• 沸点：
  525.4±50.0 °C(Predicted)
• 密度：
  1.444±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-(四氢-2H-吡喃-2-基)羟基胺 、 1-Cyclopropyl-4-(4-fluorophenyl)sulfonylpiperidine-4-carboxylic acid 在 N-甲基吗啉 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 22.0h， 以76.6%的产率得到
  参考文献：
  名称：

  Aromatic sulfone hydroxamates and their use as protease inhibitors

  摘要：

  这项发明涉及芳香砜羟肟酸酯（也称为“芳香砜羟肟酸”）及其盐，该化合物在抑制基质金属蛋白酶（也称为“基质金属蛋白酶”或“MMP”）活性和/或聚集素酶活性方面具有作用。该发明还涉及一种预防或治疗方法，包括向动物，特别是患有（或易患）与MMP和/或聚集素酶活性相关的病理状况的哺乳动物，施用此类化合物或盐以达到抑制MMP和/或聚集素酶的有效量。

  公开号：

  US20040010019A1
• 作为产物：
  描述：

  ethyl 1-cyclopropyl-4-[(4-fluorophenyl)sulfonyl]piperidine-4-carboxylate 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 以78.2%的产率得到1-Cyclopropyl-4-(4-fluorophenyl)sulfonylpiperidine-4-carboxylic acid
  参考文献：
  名称：

  Aromatic sulfone hydroxamates and their use as protease inhibitors

  摘要：

  这项发明涉及芳香砜羟肟酸酯（也称为“芳香砜羟肟酸”）及其盐，该化合物在抑制基质金属蛋白酶（也称为“基质金属蛋白酶”或“MMP”）活性和/或聚集素酶活性方面具有作用。该发明还涉及一种预防或治疗方法，包括向动物，特别是患有（或易患）与MMP和/或聚集素酶活性相关的病理状况的哺乳动物，施用此类化合物或盐以达到抑制MMP和/或聚集素酶的有效量。

  公开号：

  US20040010019A1

文献信息

• AROMATIC SULFONE HYDROXAMIC ACID METALLOPROTEASE INHIBITOR
  申请人：G.D. SEARLE & CO.

  公开号：EP1183239A1

  公开（公告）日：2002-03-06
• [EN] AROMATIC SULFONE HYDROXAMIC ACID METALLOPROTEASE INHIBITOR<br/>[FR] ACIDE HYDROXAMIQUE A SULFONE AROMATIQUE INHIBITEUR DE METALLOPROTEASES
  申请人：SEARLE & CO

  公开号：WO2000069821A1

  公开（公告）日：2000-11-23

  A treatment process is disclosed that comprises administering an effective amount of an aromatic sulfone hydroxamic acid that exhibits excellent inhibitory activity of one or more matrix metalloprotease (MMP) enzymes, such as MMP-2, MMP-9 and MMP-13, while exhibiting substantially less inhibition at least of MMP-1 to a host having a condition associated with pathological matrix metalloprotease activity. Also disclosed are metalloprotease inhibitor compounds having those selective activities, processes for manufacture of such compounds and pharmaceutical compositions using an inhibitor. A contemplated compound corresponds in structure to formula (B).
• Aromatic sulfone hydroxamates and their use as protease inhibitors
  申请人：——

  公开号：US20040010019A1

  公开（公告）日：2004-01-15

  This invention is directed to aromatic sulfone hydroxamates (also known as “aromatic sulfone hydroxamic acids”) and salts thereof that, inter alia, inhibit matrix metalloproteinase (also known as “matrix metalloprotease” or “MMP”) activity and/or aggrecanase activity. This invention also is directed to a prevention or treatment method that comprises administering such a compound or salt in an MMP-inhibiting and/or aggrecanase-inhibiting effective amount to an animal, particularly a mammal having (or disposed to having) a pathological condition associated with MMP and/or aggrecanase activity.

  这项发明涉及芳香砜羟肟酸酯（也称为“芳香砜羟肟酸”）及其盐，该化合物在抑制基质金属蛋白酶（也称为“基质金属蛋白酶”或“MMP”）活性和/或聚集素酶活性方面具有作用。该发明还涉及一种预防或治疗方法，包括向动物，特别是患有（或易患）与MMP和/或聚集素酶活性相关的病理状况的哺乳动物，施用此类化合物或盐以达到抑制MMP和/或聚集素酶的有效量。
• Orally bioavailable dual MMP-1/MMP-14 sparing, MMP-13 selective α-sulfone hydroxamates
  作者：Stephen A. Kolodziej、Susan L. Hockerman、Terri L. Boehm、Jeffery N. Carroll、Gary A. DeCrescenzo、Joseph J. McDonald、Debbie A. Mischke、Grace E. Munie、Theresa R. Fletcher、Joseph G. Rico、Nathan W. Stehle、Craig Swearingen、Daniel P. Becker

  DOI：10.1016/j.bmcl.2010.04.130

  日期：2010.6

  A series of phenyl piperidine alpha-sulfone hydroxamate derivatives has been prepared utilizing a combination of solution-phase and resin-bound library technologies to afford compounds that are potent and highly selective for MMP-13, are dual-sparing of MMP-1 and MMP-14 (MT1-MMP) and exhibit oral bioavailability in rats. (C) 2010 Elsevier Ltd. All rights reserved.