2-(6-氯-3-硝基吡啶-2-基)苯甲酸乙酯 | 433728-82-6

• 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
• 中文名称: 2-(6-氯-3-硝基吡啶-2-基)苯甲酸乙酯
• 英文名称: 2-(6-chloro-3-nitropyridin-2-yl)benzoic acid ethyl ester
• 英文别名: Ethyl 2-(6-chloro-3-nitropyridin-2-yl)benzoate
• CAS: 433728-82-6
• 化学式: C₁₄H₁₁ClN₂O₄
• 分子量: 306.705
• InChiKey: WLDYJGMVDFRTGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(6-氯-3-硝基吡啶-2-基)苯甲酸乙酯 在 镍 、 一水合肼 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 2-(4-methylpiperazin-1-yl)benzo[c]-1,5-naphthyridin-6(5H)-one
  参考文献：
  名称：

  Design and Synthesis of Poly ADP-ribose Polymerase-1 Inhibitors. 2. Biological Evaluation of Aza-5[H]-phenanthridin-6-ones as Potent, Aqueous-Soluble Compounds for the Treatment of Ischemic Injuries

  摘要：

  A series of aza-5[H]-phenanthridin-6-ones were synthesized and evaluated as inhibitors of poly ADP-ribose polymerase-1 (PARP-1). Inhibitory potency of the unsubstituted aza-5[H]-phenanthridin-6-ones (i.e., benzonaphyhyridones) was dependent on the position of the nitrogen atom within the core structure. The A ring nitrogen analogues (7-, 8-, and 10-aza-5[H]-phenanthridin-6-ones) were an order of magnitude less potent than C ring nitrogen analogues (1-, 2-, 3-, and 4-aza-5[H]-phenanthridin-6-ones). Preliminary stroke results from 1- and 2-aza-5[H]-phenanthridin-6-one prompted structure-activity relationships to be established for several 2- and 3-substituted 1-aza-5[H]-phenanthridin-6-ones. The 2-substituted 1-aza-5[H]-phenanthridin-6-ones were designed to improve the solubility and pharmacokinetic profiles for this series of PARP-1 inhibitors. Most importantly, three compounds from this series demonstrated statistically significant protective effects in rat models of stroke and heart ischemia.

  DOI：

  10.1021/jm030109s
• 作为产物：
  描述：

  2,6-二氯-3-硝基吡啶 、 2-(5,5-二甲基-1,3,2-二氧硼杂烷-2-基)苯甲酸乙酯 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 以38%的产率得到2-(6-氯-3-硝基吡啶-2-基)苯甲酸乙酯
  参考文献：
  名称：

  WO2007/51119

  摘要：

  公开号：

文献信息

• US7235557B2
  申请人：——

  公开号：US7235557B2

  公开（公告）日：2007-06-26
• US7915280B2
  申请人：——

  公开号：US7915280B2

  公开（公告）日：2011-03-29
• USRE41150E1
  申请人：——

  公开号：USRE41150E1

  公开（公告）日：2010-02-23
• WO2007/51119
  申请人：——

  公开号：——

  公开（公告）日：——
• Design and Synthesis of Poly ADP-ribose Polymerase-1 Inhibitors. 2. Biological Evaluation of Aza-5[<i>H</i>]-phenanthridin-6-ones as Potent, Aqueous-Soluble Compounds for the Treatment of Ischemic Injuries
  作者：Dana Ferraris、Yao-Sen Ko、Thomas Pahutski、Rica Pargas Ficco、Larisa Serdyuk、Christina Alemu、Chadwick Bradford、Tiffany Chiou、Randall Hoover、Shirley Huang、Susan Lautar、Shi Liang、Qian Lin、May X.-C Lu、Maria Mooney、Lisa Morgan、Yongzhen Qian、Scott Tran、Lawrence R. Williams、Qi Yi Wu、Jie Zhang、Yinong Zou、Vincent Kalish

  DOI：10.1021/jm030109s

  日期：2003.7.1

  A series of aza-5[H]-phenanthridin-6-ones were synthesized and evaluated as inhibitors of poly ADP-ribose polymerase-1 (PARP-1). Inhibitory potency of the unsubstituted aza-5[H]-phenanthridin-6-ones (i.e., benzonaphyhyridones) was dependent on the position of the nitrogen atom within the core structure. The A ring nitrogen analogues (7-, 8-, and 10-aza-5[H]-phenanthridin-6-ones) were an order of magnitude less potent than C ring nitrogen analogues (1-, 2-, 3-, and 4-aza-5[H]-phenanthridin-6-ones). Preliminary stroke results from 1- and 2-aza-5[H]-phenanthridin-6-one prompted structure-activity relationships to be established for several 2- and 3-substituted 1-aza-5[H]-phenanthridin-6-ones. The 2-substituted 1-aza-5[H]-phenanthridin-6-ones were designed to improve the solubility and pharmacokinetic profiles for this series of PARP-1 inhibitors. Most importantly, three compounds from this series demonstrated statistically significant protective effects in rat models of stroke and heart ischemia.