3-Methyl-7-phenyl-5H-isoxazolo[4,5-d]pyridazin-4-one | 129663-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-Methyl-7-phenyl-5H-isoxazolo[4,5-d]pyridazin-4-one
• 英文别名: 3-Methyl-7-phenylisoxazolo[4,5-d]pyridazin-4(5H)-one；3-methyl-7-phenyl-5H-[1,2]oxazolo[4,5-d]pyridazin-4-one
• CAS: 129663-23-6
• 化学式: C₁₂H₉N₃O₂
• 分子量: 227.222
• InChiKey: ARDPBPVVBNKLHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Methyl-7-phenyl-5H-isoxazolo[4,5-d]pyridazin-4-one 在 硫酸 、 硝酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 5-(3-bromopropyl)-3-methyl-7-(4-nitrophenyl)-5H-isoxazolo[4,5-d]pyridazin-4-one
  参考文献：
  名称：

  作为有效和口服活性抗伤害药的芳基哌嗪基烷基吡啶并吡嗪酮及其类似物：合成和作用机理的研究。

  摘要：

  在结构上与先前描述的铅A（5-{[4-（3-氯苯基）哌嗪-1-基]-丙基} -3-甲基-7-苯基异s唑并[4,5-d]哒嗪-合成4-（5H）-一）并测试其镇痛活性。许多受试分子的剂量为20 mg kg-1 po，表现出很高的抗伤害感受活性，尤其是化合物5a，11c，15a，21和22，能够将腹部收缩的数量减少50多种％在扭体测试中。铅A的药理研究使我们阐明了该化合物的作用机理，表明它通过抑制去甲肾上腺素的再摄取而发挥了镇痛作用。用α2-拮抗剂育亨宾预处理可以完全防止某些最有趣的新分子的抗伤害感受，

  DOI：

  10.1021/jm060743g
• 作为产物：
  描述：

  Ethyl 5-benzoyl-3-methyl-1,2-oxazole-4-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以66%的产率得到3-Methyl-7-phenyl-5H-isoxazolo[4,5-d]pyridazin-4-one
  参考文献：
  名称：

  Chantegrel, Bernard; Deshayes, Christian; Pujol, Bernard, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 4, p. 927 - 934

  摘要：

  DOI：

文献信息

• [(3-Chlorophenyl)piperazinylpropyl]pyridazinones and Analogues as Potent Antinociceptive Agents
  作者：Maria Paola Giovannoni、Claudia Vergelli、Carla Ghelardini、Nicoletta Galeotti、Alessandro Bartolini、Vittorio Dal Piaz

  DOI：10.1021/jm021057u

  日期：2003.3.1

  A number of [(3-chlorophenyl)piperazinylpropyl]pyridazinones and the corresponding isoxazolo-pyridazinones, showing the arylpiperazinyl substructure present in very potent antinociceptive agents reported in the literature, were synthesized and tested for their analgesic activity. The investigated compounds showed antinociceptive properties in the mouse hot-plate test (thermal nociceptive stimulus) after systemic administration with an efficacy similar to that exerted by morphine. The increase of the pain threshold induced by the compounds labeled 5a, 7, 8, and 11 was prevented by reserpine, suggesting the involvement of the noradrenergic and/or serotoninergic system in their mechanism of action. Among them, 7 and 11 showed the highest analgesic potency and efficacy together with a good ratio (133 and 200, respectively) of the minimal nontoxic dose (MNTD) to the minimal analgesic dose (MAD). Furthermore, they were also active after icv administration and in the presence of a chemical, painful stimulus (abdominal constriction test).
• Heterocyclic-fused 3(2H)-pyridazinones as potent and selective PDE IV inhibitors: Further structure-activity relationships and molecular modelling studies
  作者：Vittorio Dal Piaz、Maria Paola Giovannoni、Carla Castellana、José Maria Palacios、Jorge Beleta、Teresa Doménech、Victor Segarra

  DOI：10.1016/s0223-5234(99)80030-0

  日期：1998.10
• Isoxazolo[3,4-d]pyridazinones and analogues as Leishmania mexicana PDE inhibitors
  作者：Vittorio Dal Piaz、A Rascón、M.E Dubra、M.P Giovannoni、C Vergelli、M.C Castellana

  DOI：10.1016/s0014-827x(01)01188-0

  日期：2002.2

  A series of isoxazolopyridazinones and analogues has been prepared and evaluated as Leishmania mexicana phosphodiesterase (PDE) inhibitors. Some of the synthesized compounds showed a moderate PDE inhibitory activity at 100 muM and preliminary structure-activity relationships were discussed. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• CHANTEGREL, BERNARD;DESHAYES, CHRISTIAN;PUJOL, BERNARD;WEI, ZHONG JIA, J. HETEROCYCL. CHEM., 27,(1990) N, C. 927-934
  作者：CHANTEGREL, BERNARD、DESHAYES, CHRISTIAN、PUJOL, BERNARD、WEI, ZHONG JIA

  DOI：——

  日期：——
• Chantegrel, Bernard; Deshayes, Christian; Pujol, Bernard, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 4, p. 927 - 934
  作者：Chantegrel, Bernard、Deshayes, Christian、Pujol, Bernard、Wei, Zhong Jia

  DOI：——

  日期：——