3-(4-fluorobenzamido)quinoline | 252917-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(4-fluorobenzamido)quinoline
• 英文别名: 4-fluoro-N-quinolin-3-yl-benzamide；4-fluoro-N-quinolin-3-ylbenzamide
• CAS: 252917-79-6
• 化学式: C₁₆H₁₁FN₂O
• 分子量: 266.275
• InChiKey: DGGLXGABYZUJGW-UHFFFAOYSA-N

物化性质

• 沸点：
  365.3±22.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-fluorobenzamido)quinoline 在 五氯化磷 作用下， 反应 1.0h， 生成 4-Fluoro-N-quinolin-3-yl-benzimidoyl chloride
  参考文献：
  名称：

  Regioselectivity in the Intramolecular Substitution Reactions of Electrochemically and Photochemically Generated Aryl Radicals with Adjacent Pyridine and Quinoline Rings. A Comparison between these Reactions and Related Processes Involving Tributyltin Hydride.

  摘要：

  Cleavage of the carbon-halogen bond in 1-(3-pyridinyl)- and 1-(3-quinolinyl)-5-(1-halogenophenyl)tetrazoles leads to a sigma-radical which undergoes a cyclization reaction onto the adjacent heterocyclic ring. Bond cleavage is effected both by electrochemical reduction and by photolysis. Yields of cyclized products formed in the two types of reaction are compared. The relative advantages of the electrochemical generation of an aryl a-radical from aryl halides over reaction of the same substrate with tributyltin hydride and a radical initiator are discussed.

  DOI：

  10.3891/acta.chem.scand.53-0913
• 作为产物：
  描述：

  3-氨基喹啉 、 对氟苯甲酸 生成 3-(4-fluorobenzamido)quinoline
  参考文献：
  名称：

  N-Pyridin-3-yl- and N-quinolin-3-yl-benzamides: Modulators of Human Vanilloid Receptor 1 (TRPV1)

  摘要：

  High throughput screening of our compound library revealed a series of N-pyridyl-3-benzamides as low micromolar agonists of the human TRPV1 receptor. Synthesis of analogs in this series led to the discovery of a series of N-quinolin-3-yl-benzamides as low nanomolar antagonists of human TRPV1. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.075

文献信息

• Quinoline-derived amide modulators of vanilloid VR1 receptor
  申请人：——

  公开号：US20040192728A1

  公开（公告）日：2004-09-30

  This invention is directed to vanilloid receptor VR1 ligands. More particularly, this invention relates to quinoline-derived amides that are potent antagonists or agonists of VR1 which are useful for the treatment and prevention of inflammatory and other pain conditions in mammals.

  本发明涉及辣椒素受体VR1配体。更具体地，本发明涉及喹啉衍生物酰胺，它们是VR1的有效拮抗剂或激动剂，可用于治疗和预防哺乳动物的炎症和其他疼痛状况。
• QUINOLINE-DERIVED AMIDE MODULATORS OF VANILLOID VR1 RECEPTOR
  申请人：Codd Ellen

  公开号：US20080300236A1

  公开（公告）日：2008-12-04

  This invention is directed to vanilloid receptor VR1 ligands. More particularly, this invention relates to quinoline-derived amides that are potent antagonists or agonists of VR1 which are useful for the treatment and prevention of inflammatory and other pain conditions in mammals.

  这项发明涉及辣椒素受体VR1配体。更具体地说，这项发明涉及喹啉衍生的酰胺，它们是VR1的有效拮抗剂或激动剂，可用于治疗和预防哺乳动物的炎症和其他疼痛症状。
• [EN] QUINOLINE-DERIVED AMIDE MODULATORS OF VANILLOID VR1 RECEPTOR<br/>[FR] AMIDES DERIVES QUINOLINIQUES MODULANT LE RECEPTEUR VR1 VANILLOIDE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2004069792A3

  公开（公告）日：2005-01-20
• US8394828B2
  申请人：——

  公开号：US8394828B2

  公开（公告）日：2013-03-12
• N-Pyridin-3-yl- and N-quinolin-3-yl-benzamides: Modulators of Human Vanilloid Receptor 1 (TRPV1)
  作者：Michele C. Jetter、James J. McNally、Mark A. Youngman、Mark E. McDonnell、Adrienne E. Dubin、Nadia Nasser、Sui-Po Zhang、Ellen E. Codd、Ray W. Colburn、Dennis R. Stone、Michael R. Brandt、Christopher M. Flores、Scott L. Dax

  DOI：10.1016/j.bmcl.2008.02.075

  日期：2008.4

  High throughput screening of our compound library revealed a series of N-pyridyl-3-benzamides as low micromolar agonists of the human TRPV1 receptor. Synthesis of analogs in this series led to the discovery of a series of N-quinolin-3-yl-benzamides as low nanomolar antagonists of human TRPV1. (C) 2008 Elsevier Ltd. All rights reserved.