4-苯基-3,6-二甲基异恶唑并[3,4-d]哒嗪-7(6H)-酮 | 25506-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 4-苯基-3,6-二甲基异恶唑并[3,4-d]哒嗪-7(6H)-酮
• 英文名称: 3,6-Dimethyl-4-phenylisoxazolo<3,4-d>pyridazin-7(6H)-one
• 英文别名: ISOXAZOLO(3,4-d)PYRIDAZIN-7(6H)-ONE, 3,6-DIMETHYL-4-PHENYL-；3,6-dimethyl-4-phenyl-[1,2]oxazolo[3,4-d]pyridazin-7-one
• CAS: 25506-00-7
• 化学式: C₁₃H₁₁N₃O₂
• 分子量: 241.249
• InChiKey: XJXJGEAQOLTDAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4-苯基-3,6-二甲基异恶唑并[3,4-d]哒嗪-7(6H)-酮 在 ammonium cerium(IV) nitrate 、 硝酸 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.22h， 生成 2-Methyl-4-(2-methyl-aziridin-1-yl)-6-phenyl-5-[(E)-(3-phenyl-acryloyl)]-2H-pyridazin-3-one
  参考文献：
  名称：

  Ciciani; Dal Piaz; Paola Giovannoni, Il Farmaco, 1991, vol. 46, # 7-8, p. 873 - 885

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基肼 、 4-苯甲酰基-5-甲基-3-异恶唑羧酸乙酯 以 乙醇 为溶剂， 反应 2.0h， 生成 4-苯基-3,6-二甲基异恶唑并[3,4-d]哒嗪-7(6H)-酮
  参考文献：
  名称：

  Renzi; Pinzauti, Farmaco, Edizione Scientifica, 1969, vol. 24, # 10, p. 885 - 892

  摘要：

  DOI：

文献信息

• 4-Amino-5-substituted-3(2<i>H</i>)-pyridazinones as Orally Active Antinociceptive Agents:  Synthesis and Studies on the Mechanism of Action
  作者：Maria Paola Giovannoni、Nicoletta Cesari、Claudia Vergelli、Alessia Graziano、Claudio Biancalani、Pierfrancesco Biagini、Carla Ghelardini、Elisa Vivoli、Vittorio Dal Piaz

  DOI：10.1021/jm070161e

  日期：2007.8.1

  doses of 3-20 mg kg-1 po, showed good antinociceptive activity, reducing by more than 50% the number of writhes with respect to controls. Compounds 16c, 19a, 20a, and 28 were the most potent of the series because they were able to induce a potent antinociceptive effect at a dose of 3 mg kg-1 po. None of the active compounds at the analgesic dose provoked any visible change in normal behavior, as demonstrated

  合成了许多4-氨基-5-乙烯基吡啶酮酮和4-氨基-5-杂环吡啶酮酮，并测试了它们的镇痛活性。以3-20 mg kg-1 po的剂量测试的许多这些化合物均显示出良好的抗伤害感受活性，相对于对照而言，减少了超过50％的扭伤次数。化合物16c，19a，20a和28是该系列中最有效的化合物，因为它们能够以3 mg kg-1 po的剂量诱导有效的镇痛作用。如旋转仪测试所示，在镇痛剂量下，没有一种活性化合物引起正常行为的任何可见变化。作用机理的研究表明，用α2-拮抗剂育亨宾预处理可以完全阻止由活性化合物引起的镇痛作用，这表明α2-肾上腺素能受体的参与。
• 4-Amino-5-vinyl-3(2H)-pyridazinones and analogues as potent antinociceptive agents: Synthesis, SARs, and preliminary studies on the mechanism of action
  作者：Claudia Vergelli、Maria Paola Giovannoni、Stefano Pieretti、Amalia Di Giannuario、Vittorio Dal Piaz、Pierfrancesco Biagini、Claudio Biancalani、Alessia Graziano、Nicoletta Cesari

  DOI：10.1016/j.bmc.2007.05.035

  日期：2007.8

  A series of 4-amino-5-vinyl-3(2H)-pyridazinones and analogues were synthesized and their antinociceptive effect was evaluated in the mouse abdominal constriction model. Several of the novel compounds showed ED(50) values in the range 6-20mg/kg/sc and demonstrated to be able to completely protect all the treated animals from the effect of the noxious stimulus at 30 mg/kg/sc. SAR studies confirmed the

  合成了一系列的4-氨基-5-乙烯基-3（2H）-哒嗪酮及其类似物，并在小鼠腹部收缩模型中评估了它们的抗伤害作用。几种新化合物的ED（50）值在6-20mg / kg / sc范围内，并证明能够完全保护所有处理过的动物免受30 mg / kg / sc的有害刺激的影响。SAR研究证实，二嗪系统第4位的氨基或取代的氨基官能团和第5位的乙烯基具有重要的作用。
• Functionalized pyrazoles and pyrazolo[3,4-d]pyridazinones: Synthesis and evaluation of their phosphodiesterase 4 inhibitory activity
  作者：Pierfrancesco Biagini、Claudio Biancalani、Alessia Graziano、Nicoletta Cesari、Maria Paola Giovannoni、Agostino Cilibrizzi、Vittorio Dal Piaz、Claudia Vergelli、Letizia Crocetti、Maurizio Delcanale、Elisabetta Armani、Andrea Rizzi、Paola Puccini、Paola Maria Gallo、Daniele Spinabelli、Paola Caruso

  DOI：10.1016/j.bmc.2010.03.066

  日期：2010.5

  A series of pyrazoles and pyrazolo[3,4-d]pyridazinones were synthesized and evaluated for their PDE4 inhibitory activity. All the pyrazoles were found devoid of activity, whereas some of the novel pyrazolo[3,4-d]pyridazinones showed good activity as PDE4 inhibitors. The most potent compounds in this series showed an IC50 in the nanomolar range. The ability to inhibit TNF-alpha release in human PBMCs was determined for two representative compounds, finding values in the sub-micromolar range. SARs studies demonstrated that the best arranged groups around the heterocyclic core are 2-chloro-, 2-methyl- and 3-nitrophenyl at position 2, an ethyl ester at position 4 and a small alkyl group at position 6. Molecular modeling studies performed on a representative compound allowed to define its binding mode to the PDE4B isoform. (C) 2010 Elsevier Ltd. All rights reserved.
• Dal Piaz; Ciciani; Giovannoni, Il Farmaco, 1991, vol. 46, # 3, p. 435 - 447
  作者：Dal Piaz、Ciciani、Giovannoni

  DOI：——

  日期：——
• Piaz, Vittorio Dal; Ciciani, Giovanna; Chimichi, Stefano, Heterocycles, 1985, vol. 23, # 2, p. 365 - 369
  作者：Piaz, Vittorio Dal、Ciciani, Giovanna、Chimichi, Stefano

  DOI：——

  日期：——