2-(4-氨基-3-吡啶) N,N-双(1-甲基乙基)-苯甲酰胺 | 433728-73-5

• 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-(4-氨基-3-吡啶) N,N-双(1-甲基乙基)-苯甲酰胺
• 中文别名: 2-(4-氨基-3-吡啶)N,N-双(1-甲基乙基)-苯甲酰胺
• 英文名称: 2-(4-aminopyridin-3-yl)-N,N-diisopropylbenzamide
• 英文别名: 2-(4-amino-3-pyridinyl)-N,N-bis(1-methylethyl)benzamide；2-(4-Amino-3-pyridinyl) N,N-bis(1-methylethyl)-benzamide；2-(4-aminopyridin-3-yl)-N,N-di(propan-2-yl)benzamide
• CAS: 433728-73-5
• 化学式: C₁₈H₂₃N₃O
• 分子量: 297.4
• InChiKey: KRDXCIKACUMFSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-氨基-3-吡啶) N,N-双(1-甲基乙基)-苯甲酰胺 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到5H-苯并[c][1,6]萘啶-6-酮
  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：

  4-氨基-3-碘吡啶 、 2-(二异丙基羰基)苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 以83%的产率得到2-(4-氨基-3-吡啶) N,N-双(1-甲基乙基)-苯甲酰胺
  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

文献信息

• Compounds and their use
  申请人：——

  公开号：US20030022883A1

  公开（公告）日：2003-01-30

  This invention relates to compounds, pharmaceutical compositions, and methods of using the disclosed compounds for inhibiting PARP.

  这项发明涉及化合物、药物组合物以及使用所披露的化合物来抑制PARP的方法。
• Compounds and their uses
  申请人：Ferraris V. Dana

  公开号：US20060142266A1

  公开（公告）日：2006-06-29

  This invention relates to compounds, pharmaceutical compositions, and methods of using the disclosed compounds for inhibiting PARP.

  本发明涉及化合物、制药组合物和使用所披露的化合物抑制PARP的方法。
• USRE041150E1
  申请人：——

  公开号：——

  公开（公告）日：——
• BENZOAZEPINE AND BENZODIAZEPINE DERIVATIVES AND THEIR USE AS PARP INHIBITORS
  申请人：GUILFORD PHARMACEUTICALS INC.

  公开号：EP1339402A2

  公开（公告）日：2003-09-03
• US6887996B2
  申请人：——

  公开号：US6887996B2

  公开（公告）日：2005-05-03