2-(2,3,5,6-tetrafluoro-3'-trifluoromethoxy-biphenyl-4-ylcarbamoyl)-cyclopent-1-enecarboxylic acid

• 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: 2-(2,3,5,6-tetrafluoro-3'-trifluoromethoxy-biphenyl-4-ylcarbamoyl)-cyclopent-1-enecarboxylic acid
• 英文别名: 2-(2,3,5,6-tetrafluoro-3'-trifluoromethoxybiphenyl-4-ylcarbamoyl)cyclopent-1-enecarboxylic acid；2-[[2,3,5,6-Tetrafluoro-4-[3-(trifluoromethoxy)phenyl]phenyl]carbamoyl]cyclopentene-1-carboxylic acid
• 化学式: C₂₀H₁₂F₇NO₄
• 分子量: 463.308
• InChiKey: HXVDQTDBVMYWOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-(2,3,5,6-tetrafluoro-3'-trifluoromethoxy-biphenyl-4-ylcarbamoyl)-cyclopent-1-enecarboxylic acid 在 4-二甲氨基吡啶 、 磺酰胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 N1-sulfamoyl-N2-(2,3,5,6-tetrafluoro-3'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)cyclopent-1-ene-1,2-dicarboxamide
  参考文献：
  名称：

  [EN] DHODH INHIBITORS CONTAINING A CARBOXYLIC ACID BIOISOSTERE
  [FR] INHIBITEURS DE DHODH CONTENANT UN BIOISOSTÈRE D'ACIDE CARBOXYLIQUE

  摘要：

  The invention relates to novel, optionally deuterated compounds of Formula (I) and their use as medicament.

  公开号：

  WO2023118576A1
• 作为产物：
  描述：

  3-(三氟甲氧基)苯硼酸 在 potassium fluoride 、 钯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(2,3,5,6-tetrafluoro-3'-trifluoromethoxy-biphenyl-4-ylcarbamoyl)-cyclopent-1-enecarboxylic acid
  参考文献：
  名称：

  Discovery of a novel series of DHODH inhibitors by a docking procedure and QSAR refinement

  摘要：

  A novel series of DHODH inhibitors was developed based on a lead which was obtained by a docking procedure and a medicinal chemistry exploration. The activity of the initial lead was improved by a QSAR method to yield low nanomolar inhibitors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.021

文献信息

• SAR, species specificity, and cellular activity of cyclopentene dicarboxylic acid amides as DHODH inhibitors
  作者：Johann Leban、Martin Kralik、Jan Mies、Michael Gassen、Karin Tentschert、Roland Baumgartner

  DOI：10.1016/j.bmcl.2005.07.053

  日期：2005.11

  Novel DHODH inhibitors were developed based on a previously described series by introduction of heteroatoms into the cyclopentene ring and hydroxyl groups attached to it. Also, the hydrophobic biphenyl side chain was replaced with benzyloxy phenyl groups. Activities on human, rat, and mouse enzymes indicate a species specificity of these inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.
• DIHYDROOROTATE-DEHYDROGENASEE INHIBITORS AS VIROSTATIC COMPOUNDS
  申请人：Panoptes Pharma Ges.m.b.H.

  公开号：EP2427186B1

  公开（公告）日：2022-01-12
• COMBINATIONAL THERAPY COMPRISING DHODH INHIBITOR AND METHOTREXATE FOR TREATING AUTOIMMUNE DISEASE
  申请人：4SC AG

  公开号：EP2362771A1

  公开（公告）日：2011-09-07
• NOVEL METHODS FOR TREATING NEURODEGENERATIVE DISEASES
  申请人：Genzyme Corporation

  公开号：EP3071199A2

  公开（公告）日：2016-09-28
• Method of identifying inhibitors of DHODH
  申请人：Leban Johann

  公开号：US20070027193A1

  公开（公告）日：2007-02-01

  The present invention provides a compound capable of binding to the ubiquinone binding site of DHODH which contains a non-aromatic ring system as a core structure, a group capable of interacting with structural elements of subsite 2 or 3 of the ubiquinone binding site of DHODH and a group capable of interacting hydrophobically with structural elements of subsite 1 of the ubiquinone binding site of DHODH. Furthermore, the present invention provides a compound capable of binding to the ubiquinone binding site of DHODH which contains an aromatic ring system as a core structure, a group capable of interacting with residues His 56 and/or Tyr 356 of subsite 3 of the ubiquinone binding site of DHODH and a group capable of interacting hydrophobically with structural elements of subsite 1 of the ubiquinone binding site of DHODH.