2-[3-(nitro)-6-(4-methylpiperazin-1-yl)pyridin-2-yl]-N,N-diisopropylbenzamide | 433728-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-[3-(nitro)-6-(4-methylpiperazin-1-yl)pyridin-2-yl]-N,N-diisopropylbenzamide
• 英文别名: N,N-diisopropyl-2-[6-(4-methylpiperazin-1-yl)-3-nitro-pyridin-2-yl]benzamide；2-[6-(4-methylpiperazin-1-yl)-3-nitropyridin-2-yl]-N,N-di(propan-2-yl)benzamide
• CAS: 433728-68-8
• 化学式: C₂₃H₃₁N₅O₃
• 分子量: 425.531
• InChiKey: UWADEISCNCGIQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  85.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[3-(nitro)-6-(4-methylpiperazin-1-yl)pyridin-2-yl]-N,N-diisopropylbenzamide 在 palladium on activated charcoal 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -78.0~20.0 ℃ 、206.84 kPa 条件下， 反应 2.0h， 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 在 四(三苯基膦)钯 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 18.0h， 生成 2-[3-(nitro)-6-(4-methylpiperazin-1-yl)pyridin-2-yl]-N,N-diisopropylbenzamide
  参考文献：
  名称：

  USE OF SUBSTITUTED ISOQUINOLINONES, ISOQUINOLINDIONES, ISOQUINOLINTRIONES AND DIHYDROISOQUINOLINONES OR IN EACH CASE SALTS THEREOF AS ACTIVE AGENTS AGAINST ABIOTIC STRESS IN PLANTS

  摘要：

  使用通式（I）中的替代的异喹啉酮、异喹啉二酮、异喹啉三酮和二氢异喹啉酮或它们的相应盐，其中通式（I）中的基团对应于描述中给出的定义，用于增强植物对非生物胁迫的耐受性，增强植物生长和/或增加植物产量，并选择性地制备上述化合物的过程。

  公开号：

  US20140302987A1
• 作为试剂：
  描述：

  2-(6-chloro-3-nitropyridin-2-yl)-N,N-diisopropylbenzamide 、 N-甲基哌嗪 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 在 乙酸乙酯 、 magnesium sulfate 、 2-[3-(nitro)-6-(4-methylpiperazin-1-yl)pyridin-2-yl]-N,N-diisopropylbenzamide 、 甲醇 、 氩 、 钯 、 氢气 、 2-[3-amino-6-(4-methylpiperazin-1-yl)pyridin-2-yl]-N,N-diisopropylbenzamide 、 四氢呋喃 作用下， 以 水 、 乙酸乙酯 、 四氢呋喃 为溶剂， 反应 8.25h， 以gave 2-(4-methylpiperazin-1-yl)benzo[c]-1,5-naphthyridin-6(5H)-one (90 mg, 52% of theory) in the form of a colourless solid的产率得到2-(4-methylpiperazin-1-yl)benzo[c]-1,5-naphthyridin-6(5H)-one
  参考文献：
  名称：

  Use of substituted isoquinolinones, isoquinolindiones, isoquinolintriones and dihydroisoquinolinones or in each case salts thereof as active agents against abiotic stress in plants

  摘要：

  使用通式（I）中的取代的异喹啉酮，异喹啉二酮，异喹啉三酮和二氢异喹啉酮或它们的相应盐，其中通式（I）中的基团符合说明中给出的定义，用于增强植物对非生物胁迫的耐受性，增强植物生长和/或增加植物产量，以及选定的制备上述化合物的过程。

  公开号：

  US09173395B2

文献信息

• USE OF SUBSTITUTED ISOQUINOLINONES, ISOQUINOLINDIONES, ISOQUINOLINTRIONES AND DIHYDROISOQUINOLINONES OR IN EACH CASE SALTS THEREOF AS ACTIVE AGENTS AGAINST ABIOTIC STRESS IN PLANTS
  申请人：Frackenpohl Jens

  公开号：US20140302987A1

  公开（公告）日：2014-10-09

  Use of substituted isoquinolinones, isoquinolinediones, isoquinolinetriones and dihydroisoquinolinones of the general formula (I) or their respective salts where the radicals in the general formula (I) correspond to the definitions given in the description, for enhancing stress tolerance in plants to abiotic stress, for strengthening plant growth and/or for increasing plant yield, and selected processes for preparing the compounds mentioned above.

  使用通式（I）中的替代的异喹啉酮、异喹啉二酮、异喹啉三酮和二氢异喹啉酮或它们的相应盐，其中通式（I）中的基团对应于描述中给出的定义，用于增强植物对非生物胁迫的耐受性，增强植物生长和/或增加植物产量，并选择性地制备上述化合物的过程。
• US9173395B2
  申请人：——

  公开号：US9173395B2

  公开（公告）日：2015-11-03
• 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.