4-methoxy-2-[2-hydroxy-3(4-phenyl-1-piperazinyl)]propyl-2,3-dihydro-6-methyl-1,3-dioxo-1H-pyrrolo[3,4-c]pyridine | 578742-19-5

• 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: 4-methoxy-2-[2-hydroxy-3(4-phenyl-1-piperazinyl)]propyl-2,3-dihydro-6-methyl-1,3-dioxo-1H-pyrrolo[3,4-c]pyridine
• 英文别名: 4-methoxy-2-[2-hydroxy-3-(4-phenyl-1-piperazinyl)]propyl-2,3-dihydro-6-methyl-1,3-dioxo-1H-pyrrolo[,4-c]pyridine；4-methoxy-2-[2-hydroxy-3-(4-phenyl-1-piperazinyl)propyl]-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione；2-[2-Hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-4-methoxy-6-methylpyrrolo[3,4-c]pyridine-1,3-dione
• CAS: 578742-19-5
• 化学式: C₂₂H₂₆N₄O₄
• 分子量: 410.473
• InChiKey: QHEBDDRAHVHBDC-UHFFFAOYSA-N

物化性质

• 熔点：
  190-192 °C(Solv: ethanol (64-17-5))
• 沸点：
  631.1±55.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  86.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-methoxy-2-[2-hydroxy-3(4-phenyl-1-piperazinyl)]propyl-2,3-dihydro-6-methyl-1,3-dioxo-1H-pyrrolo[3,4-c]pyridine 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propylcarbamoyl]-2-methoxy-6-methylisonicotinic acid
  参考文献：
  名称：

  Muszalska, Izabela, Acta poloniae pharmaceutica, 2010, vol. 67, # 3, p. 233 - 238

  摘要：

  DOI：
• 作为产物：
  描述：

  4-methoxy-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 4-methoxy-2-[2-hydroxy-3(4-phenyl-1-piperazinyl)]propyl-2,3-dihydro-6-methyl-1,3-dioxo-1H-pyrrolo[3,4-c]pyridine
  参考文献：
  名称：

  Investigations on the synthesis and pharmacological properties of 4-alkoxy-2-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl]-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones

  摘要：

  Synthesis of 2-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl] derivatives of 4-alkoxy-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)diones (8-12) is described. The chlorides used in the above synthesis can exist in two isomeric forms: chain (18-20) and cyclic (19a, 20a). The compounds 8-12 exhibited potent analgesic activity which was superior than that of acetylsalicylic acid in two different tests. Most of the investigated imides suppressed significantly spontaneous locomotor activity in mice. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01302-2

文献信息

• Antinociceptive, antiedematous, and antiallodynic activity of 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione derivatives in experimental models of pain
  作者：Anna Dziubina、Dominika Szkatuła、Joanna Gdula-Argasińska、Magdalena Kotańska、Barbara Filipek

  DOI：10.1007/s00210-019-01783-3

  日期：2020.5

  The aim of the presented study was to examine the potential antinociceptive, antiedematous (anti-inflammatory), and antiallodynic activities of two 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione derivatives (DSZ 1 and DSZ 3) in various experimental models of pain. For this purpose, the hot plate test, the capsaicin test, the formalin test, the carrageenan model, and oxaliplatin-induced allodynia tests were performed. In the hot plate test, only DSZ 1 in the highest dose (20 mg/kg) was active but its effects appear to be due to sedatation rather than antinociceptiveness. In capsaicin-induced neurogenic pain model, both compounds displayed a significant antinociceptive activity. In the formalin test, DSZ 1 and DSZ 3 (5-20 mg/kg) revealed antinociceptive activity in both phases but it was more pronounced in the second phase of the test. In this test, pretreatment with caffeine, DPCPX reversed the antinociceptive effect of DSZ 3. On the other hand, pretreatment with L-NAME diminished the antinociceptive effect of DSZ 1. Pretreatment with naloxone did not affect antinociceptive activity of both compounds. Similar to ketoprofen, DSZ 1 and DSZ 3 showed antiedematous (antiinflammatory) and antihyperalgesic activity, and similar to lidocaine local anesthetic activity. Furthermore, both compounds (5 and 10 mg/kg) reduced tactile allodynia in acute and chronic phases of neuropathic pain. In the in vitro studies, DSZ 1 and DSZ 3 reduced the COX-2 level in LPS-activated RAW 264.7 cells, which suggests their anti-inflammatory activity. In conclusion, both DSZ 1 and DSZ 3 displayed broad spectrum of activity in several pain models, including neurogenic, tonic, inflammatory, and chemotherapy-induced peripheral neuropathic pain.
• Investigations on the synthesis and pharmacological properties of 4-alkoxy-2-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl]-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones
  作者：Helena Śladowska、Barbara Filipek、Dominika Szkatuła、Aleksandra Sabiniarz、Małgorzata Kardasz、Joanna Potoczek、Maria Sieklucka-Dziuba、Grażyna Rajtar、Zdzisław Kleinrok、Tadeusz Lis

  DOI：10.1016/s0014-827x(02)01302-2

  日期：2002.11

  Synthesis of 2-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl] derivatives of 4-alkoxy-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)diones (8-12) is described. The chlorides used in the above synthesis can exist in two isomeric forms: chain (18-20) and cyclic (19a, 20a). The compounds 8-12 exhibited potent analgesic activity which was superior than that of acetylsalicylic acid in two different tests. Most of the investigated imides suppressed significantly spontaneous locomotor activity in mice. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Muszalska, Izabela, Acta poloniae pharmaceutica, 2010, vol. 67, # 3, p. 233 - 238
  作者：Muszalska, Izabela

  DOI：——

  日期：——