5-(3-Cyanophenyl)nicotinic acid | 893740-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(3-Cyanophenyl)nicotinic acid
• 英文别名: 5-(3-cyanophenyl)pyridine-3-carboxylic acid
• CAS: 893740-73-3
• 化学式: C₁₃H₈N₂O₂
• 分子量: 224.219
• InChiKey: IATGPTBSYAGCRF-UHFFFAOYSA-N

物化性质

• 沸点：
  485.4±40.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-Cyanophenyl)nicotinic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 5-(3-Cyanophenyl)-3-pyridinecarbonyl chloride
  参考文献：
  名称：

  Discovery of a new chemical series of BRD4(1) inhibitors using protein-ligand docking and structure-guided design

  摘要：

  Bromodomains are key transcriptional regulators that are thought to be druggable epigenetic targets for cancer, inflammation, diabetes and cardiovascular therapeutics. Of particular importance is the first of two bromodomains in bromodomain containing 4 protein (BRD4(1)). Protein-ligand docking in BRD4(1) was used to purchase a small, focused screening set of compounds possessing a large variety of core structures. Within this set, a small number of weak hits each contained a dihydroquinoxalinone ring system. We purchased other analogs with this ring system and further validated the new hit series and obtained improvement in binding inhibition. Limited exploration by new analog synthesis showed that the binding inhibition in a FRET assay could be improved to the low mu M level making this new core a potential hit-to-lead series. Additionally, the predicted geometries of the initial hit and an improved analog were confirmed by X-ray co-crystallography with BRD4(1). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.107

文献信息

• Discovery of a new chemical series of BRD4(1) inhibitors using protein-ligand docking and structure-guided design
  作者：Bryan C. Duffy、Shuang Liu、Gregory S. Martin、Ruifang Wang、Ming Min Hsia、He Zhao、Cheng Guo、Michael Ellis、John F. Quinn、Olesya A. Kharenko、Karen Norek、Emily M. Gesner、Peter R. Young、Kevin G. McLure、Gregory S. Wagner、Damodharan Lakshminarasimhan、Andre White、Robert K. Suto、Henrik C. Hansen、Douglas B. Kitchen

  DOI：10.1016/j.bmcl.2015.04.107

  日期：2015.7

  Bromodomains are key transcriptional regulators that are thought to be druggable epigenetic targets for cancer, inflammation, diabetes and cardiovascular therapeutics. Of particular importance is the first of two bromodomains in bromodomain containing 4 protein (BRD4(1)). Protein-ligand docking in BRD4(1) was used to purchase a small, focused screening set of compounds possessing a large variety of core structures. Within this set, a small number of weak hits each contained a dihydroquinoxalinone ring system. We purchased other analogs with this ring system and further validated the new hit series and obtained improvement in binding inhibition. Limited exploration by new analog synthesis showed that the binding inhibition in a FRET assay could be improved to the low mu M level making this new core a potential hit-to-lead series. Additionally, the predicted geometries of the initial hit and an improved analog were confirmed by X-ray co-crystallography with BRD4(1). (C) 2015 Elsevier Ltd. All rights reserved.