2-(4-bromophenyl)-6-fluoro-4-hydroxyquinoline-3-carbonitrile | 881311-60-0

• 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: 2-(4-bromophenyl)-6-fluoro-4-hydroxyquinoline-3-carbonitrile
• 英文别名: 2-(4-bromophenyl)-6-fluoro-4-oxo-1H-quinoline-3-carbonitrile
• CAS: 881311-60-0
• 化学式: C₁₆H₈BrFN₂O
• 分子量: 343.155
• InChiKey: BBKQAMWRYCDARX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)-6-fluoro-4-hydroxyquinoline-3-carbonitrile 在 1,4-双(二苯基膦丁烷)二氯化钯 sodium carbonate 、 三氯氧磷 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-chloro-2-(2'-ethoxybiphenyl-4-yl)-6-fluoroquinoline-3-carbonitrile
  参考文献：
  名称：

  PDE-10A inhibitors as insulin secretagogues

  摘要：

  Modulation of cAMP levels has been linked to insulin secretion in preclinical animal models and in humans. The high expression of PDE-10A in pancreatic islets suggested that inhibition of this enzyme may provide the necessary modulation to elicit increased insulin secretion. Using an HTS approach, we have identified quinoline-based PDE-10A inhibitors as insulin secretagogues in vitro. Optimized compounds were evaluated in vivo where improvements in glucose tolerance and increases in insulin secretion were measured. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.061
• 作为产物：
  描述：

  5-氟靛红酸酐 、 4-溴苯甲酰乙腈 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以84%的产率得到2-(4-bromophenyl)-6-fluoro-4-hydroxyquinoline-3-carbonitrile
  参考文献：
  名称：

  [EN] PHENYL-SUBSTITUTED QUINOLINE AND QUINAZOLINE COMPOUNDS FOR THE TREATMENT OF DIABETES
  [FR] COMPOSES A BASE DE QUINOLEINE ET DE QUINAZOLINE A SUBSTITUTION PHENYLIQUE POUR LE TRAITEMENT DU DIABETE

  摘要：

  公开号：

  WO2006034491A3

文献信息

• [EN] PHENYL-SUBSTITUTED QUINOLINE AND QUINAZOLINE COMPOUNDS FOR THE TREATMENT OF DIABETES<br/>[FR] COMPOSES A BASE DE QUINOLEINE ET DE QUINAZOLINE A SUBSTITUTION DE PHENYLIQUE POUR LE TRAITEMENT DU DIABETE
  申请人：BAYER PHARMACEUTICALS CORP

  公开号：WO2006034512A2

  公开（公告）日：2006-03-30

  The invention relates to 2-phenyl-substituted quinoline and quinazoline compounds, pharmaceutical compositions, and methods for treating diabetes and related disorders.
• [EN] PHENYL-SUBSTITUTED QUINOLINE AND QUINAZOLINE COMPOUNDS FOR THE TREATMENT OF DIABETES<br/>[FR] COMPOSES A BASE DE QUINOLEINE ET DE QUINAZOLINE A SUBSTITUTION PHENYLIQUE POUR LE TRAITEMENT DU DIABETE
  申请人：BAYER PHARMACEUTICALS CORP

  公开号：WO2006034491A3

  公开（公告）日：2006-08-24
• PDE-10A inhibitors as insulin secretagogues
  作者：Louis-David Cantin、Steven Magnuson、David Gunn、Nicole Barucci、Marina Breuhaus、William H. Bullock、Jennifer Burke、Thomas H. Claus、Michelle Daly、Lynn DeCarr、Ann Gore-Willse、Helana Hoover-Litty、Ellalahewage S. Kumarasinghe、Yaxin Li、Sidney X. Liang、James N. Livingston、Timothy Lowinger、Margit MacDougall、Herbert O. Ogutu、Alan Olague、Ronda Ott-Morgan、Robert W. Schoenleber、Adrian Tersteegen、Philip Wickens、Zhonghua Zhang、Jian Zhu、Lei Zhu、Laurel J. Sweet

  DOI：10.1016/j.bmcl.2007.02.061

  日期：2007.5

  Modulation of cAMP levels has been linked to insulin secretion in preclinical animal models and in humans. The high expression of PDE-10A in pancreatic islets suggested that inhibition of this enzyme may provide the necessary modulation to elicit increased insulin secretion. Using an HTS approach, we have identified quinoline-based PDE-10A inhibitors as insulin secretagogues in vitro. Optimized compounds were evaluated in vivo where improvements in glucose tolerance and increases in insulin secretion were measured. (c) 2007 Elsevier Ltd. All rights reserved.