3-吡啶羧酸,1,2,5,6-四氢-4-苯基-1-(苯基甲基)-,甲基酯 | 114139-37-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 3-吡啶羧酸,1,2,5,6-四氢-4-苯基-1-(苯基甲基)-,甲基酯
• 英文名称: 1,2,5,6-Tetrahydro-4-phenyl-1-(phenylmethyl)-3-pyridinecarboxylic acid, methyl ester
• 英文别名: methyl 1-benzyl-4-phenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 114139-37-6
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: FZOFVXIGRQWHDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-吡啶羧酸,1,2,5,6-四氢-4-苯基-1-(苯基甲基)-,甲基酯 在 palladium on activated charcoal lithium hydroxide 、 三氯化铝 、 联苯基氨基磷酸酯 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 3-Ethenylsulfonyl-1,2,4,5-tetrahydrobenzo[c][1,7]naphthyridin-6-one
  参考文献：
  名称：

  Design and synthesis of poly(ADP-ribose)polymerase-1 (PARP-1) inhibitors. Part 3: In vitro evaluation of 1,3,4,5-Tetrahydro-benzo[c][1,6]- and [c][1,7]-naphthyridin-6-ones

  摘要：

  The 1,3,4,5-tetrahydro-benzo[c][1,6]- and [c][1,7]-napthyridin-6-ones are presented as a potent class of PARP-1 inhibitors. Derivatives of these partially saturated aza-5[H]-phenanthridin-6-ones were designed and synthesized with tertiary amines for salt formation. thus enhancing aqueous solubility, iv formulation and their potential use in acute ischemic injuries (i.e., myocardial ischemia and stroke). We found that partial saturation of the C-ring results in derivatives that are several times more potent than the aromatic C-ring derivatives. The general synthetic routes are presented herein as well as thorough in vitro potencies and SAR discussion for selected derivatives. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00465-7
• 作为产物：
  描述：

  1-苄基-3-甲氧基羰酰-4-哌啶酮 在 四(三苯基膦)钯 、 sodium hydride 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 乙醚 为溶剂， 生成 3-吡啶羧酸,1,2,5,6-四氢-4-苯基-1-(苯基甲基)-,甲基酯
  参考文献：
  名称：

  Design and synthesis of poly(ADP-ribose)polymerase-1 (PARP-1) inhibitors. Part 3: In vitro evaluation of 1,3,4,5-Tetrahydro-benzo[c][1,6]- and [c][1,7]-naphthyridin-6-ones

  摘要：

  The 1,3,4,5-tetrahydro-benzo[c][1,6]- and [c][1,7]-napthyridin-6-ones are presented as a potent class of PARP-1 inhibitors. Derivatives of these partially saturated aza-5[H]-phenanthridin-6-ones were designed and synthesized with tertiary amines for salt formation. thus enhancing aqueous solubility, iv formulation and their potential use in acute ischemic injuries (i.e., myocardial ischemia and stroke). We found that partial saturation of the C-ring results in derivatives that are several times more potent than the aromatic C-ring derivatives. The general synthetic routes are presented herein as well as thorough in vitro potencies and SAR discussion for selected derivatives. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00465-7

文献信息

• [EN] COMPOUNDS, DERIVATIVES, COMPOSITIONS, PREPARATION AND USES<br/>[FR] COMPOSES, DERIVES, COMPOSITIONS, LEUR PREPARATION ET LEURS UTILISATIONS
  申请人：GUILFORD PHARM INC

  公开号：WO2003014121A1

  公开（公告）日：2003-02-20

  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、药物组合物以及使用所披露的化合物抑制PARP的方法。
• US7247641B2
  申请人：——

  公开号：US7247641B2

  公开（公告）日：2007-07-24
• Design and synthesis of poly(ADP-ribose)polymerase-1 (PARP-1) inhibitors. Part 3: In vitro evaluation of 1,3,4,5-Tetrahydro-benzo[c][1,6]- and [c][1,7]-naphthyridin-6-ones
  作者：Dana Ferraris、Rica Pargas Ficco、Thomas Pahutski、Susan Lautar、Shirley Huang、Jie Zhang、Vincent Kalish

  DOI：10.1016/s0960-894x(03)00465-7

  日期：2003.8

  The 1,3,4,5-tetrahydro-benzo[c][1,6]- and [c][1,7]-napthyridin-6-ones are presented as a potent class of PARP-1 inhibitors. Derivatives of these partially saturated aza-5[H]-phenanthridin-6-ones were designed and synthesized with tertiary amines for salt formation. thus enhancing aqueous solubility, iv formulation and their potential use in acute ischemic injuries (i.e., myocardial ischemia and stroke). We found that partial saturation of the C-ring results in derivatives that are several times more potent than the aromatic C-ring derivatives. The general synthetic routes are presented herein as well as thorough in vitro potencies and SAR discussion for selected derivatives. (C) 2003 Elsevier Ltd. All rights reserved.