6-(4-Chloro-phenyl)-4-phenyl-2H-pyridazin-3-one | 75616-30-7

• 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: 6-(4-Chloro-phenyl)-4-phenyl-2H-pyridazin-3-one
• 英文别名: 3-(4-chlorophenyl)-5-phenyl-1H-pyridazin-6-one
• CAS: 75616-30-7
• 化学式: C₁₆H₁₁ClN₂O
• 分子量: 282.729
• InChiKey: KUUHNLBCZYSOQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(4-Chloro-phenyl)-4-phenyl-2H-pyridazin-3-one 在 tetraphosphorus decasulfide 作用下， 以 xylene 为溶剂， 反应 1.0h， 以25%的产率得到6-p-chlorophenyl-4-phenylpyridazin-3(2H)-thione
  参考文献：
  名称：

  Ismail, M. Fekry; Kaddah, A. M.; Elkafrawy, A. F., Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 3, p. 415 - 420

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(4-氯苯基)-4-氧代-2-苯基丁酸 在 溴 、 一水合肼 作用下， 以 溶剂黄146 、 正丁醇 为溶剂， 反应 9.0h， 生成 6-(4-Chloro-phenyl)-4-phenyl-2H-pyridazin-3-one
  参考文献：
  名称：

  Coudert, P.; Couquelet, J.; Tronche, P., Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 799 - 802

  摘要：

  DOI：

文献信息

• MICROWAVE ASSISTED SYNTHESIS OF 4,6-DIARYLPYRIDAZIN-3(2<i>H</i>)-ONES IN SOLID STATE
  作者：C. Meenakshi、V. Ramamoorthy、S. Muthusubramanian、S. Sivasubramanian

  DOI：10.1081/scc-100103250

  日期：2001.1

  Microwave assisted synthesis of dihydropyridazin-3(2H)-ones and the subsequent dehydrogenation using selenium dioxide are described.

  微波辅助合成 dihydropyridazin-3(2H)-ones 和随后使用二氧化硒脱氢。
• Synthesis and pharmacological evaluation of N-substituted 4,6-diaryl-3-pyridazinones as Analgesic, antiinflammatory and antipyretic agents.
  作者：Catherine RUBAT、Pascal COUDERT、Pierre TRONCHE、Jeanine BASTIDE、Pierre BASTIDE、Anne-Marie PRIVAT

  DOI：10.1248/cpb.37.2832

  日期：——

  The synthesis and the pharmacological evaluation of 19 new 4,6-diaryl-3-pyridazinones are reported. All compounds were screened for analgesic, antiinflammatory and antipyretic activities. Introduction of an arylpiperazinomethyl moiety in the 2-position of the pyridazinone ring resulted in the most potent activities. Compounds 2a, 2b, 2h and 2i exhibited a higher analgesic activity than did aspirin

  报道了19种新的4，6-二芳基-3-吡嗪酮的合成和药理学评价。筛选所有化合物的镇痛，抗炎和解热活性。在哒嗪酮环的2-位引入芳基哌嗪子甲基部分导致最有效的活性。在热板试验中，化合物2a，2b，2h和2i的镇痛活性高于阿司匹林或去甲多米诺林。
• Synthesis and Trazodone-like Analgesic Activity of 4-Phenyl-6-aryl-2-(3-(4-arylpiperazin-1-yl)propyl)pyridazin-3-ones.
  作者：Florence ROHET、Catherine RUBAT、Pascal COUDERT、Eliane ALBUISSON、Jacques COUQUELET

  DOI：10.1248/cpb.44.980

  日期：——

  A series of 4, 6-diaryl pyridazinones, chemically related to trazodone, was synthesized and evaluated for analgesic activity. With ED50 values ranging from 8.4 to 46.7 mg kg-1 i.p. in the phenylbenzoquinone-induced writhing test (PBQ test), most compounds were several times more potent than acetaminophen (ED50=231.3 mg kg-1 i.p.) and noramidopyrine (ED50=68.5 mg kg-1 i.p.). A multiple linear regression analysis demonstrated a correlation between antinociceptive activity and lipophilicity, as well as electronic and steric factors. The most active pyridazinones 2c and 2j exhibited minimal sedative and neurotoxic effects at the dose of 25 mg kg-1 i.p. They were devoid of activity in the hot plate test and their analgesic activity was not significantly reversed by naloxone in the PBQ test. The antinociceptive response induced by morphine (0.15 mg kg-1 s.c.) in the PBQ test was greatly potentiated by 2c and 2j administered at the low doses of 1 and 2.5 mg kg-1 i.p., respectively. On the other hand, their analgesic effects were enhanced synergistically by 5-hydroxytryptophan combined with carbidopa. All these data imply that a significant part of the antinociceptive effect induced by 2c and 2j may involve both opioid and serotenergic pathways. In addition, these two pyridazinones did not exhibit any antidepressant properties in the forced swimming test, nor did they potentiate yohimbine-induced toxicity.

  我们合成了一系列与曲唑酮化学相关的 4，6-二芳基哒嗪酮，并对其镇痛活性进行了评估。在苯醌诱导的蠕动试验（PBQ 试验）中，大多数化合物的 ED50 值为 8.4 至 46.7 毫克/千克，是对乙酰氨基酚（ED50=231.3 毫克/千克）和去甲氨基嘌呤（ED50=68.5 毫克/千克）的数倍。多元线性回归分析表明，抗痛活性与亲脂性以及电子和立体因子之间存在相关性。活性最强的哒嗪酮 2c 和 2j 在 25 毫克/公斤-1 毫升的给药剂量下表现出最小的镇静和神经毒性作用。它们在热板试验中没有活性，在 PBQ 试验中纳洛酮也不会显著逆转它们的镇痛活性。在 PBQ 试验中，吗啡（0.15 毫克/千克-1 毫升）诱导的镇痛反应在 2c 和 2j 分别以 1 毫克/千克-1 毫升和 2.5 毫克/千克-1 毫升的低剂量给药后大大增强。另一方面，5-羟色氨酸与卡比多巴联合使用可协同增强这两种药物的镇痛效果。所有这些数据都意味着，2c 和 2j 所诱导的抗痛觉作用的很大一部分可能涉及阿片和血清能途径。此外，这两种哒嗪类药物在强迫游泳试验中没有表现出任何抗抑郁特性，也没有增强育亨宾引起的毒性。
• Synthesis of New Pyridazinones Substituted by 4-Arylpiperazin-1-yl-carbonylalkyl Moieties and their Analgesic Properties in Mice
  作者：P. Coudert、C. Rubat、F. Rohet、F. Leal、J. Fialip、J. Couquelet

  DOI：10.1211/146080800128736259

  日期：2000.9.1
• Castanier; Rubat; Coudert, Arzneimittel-Forschung/Drug Research, 1995, vol. 45, # 9, p. 947 - 951
  作者：Castanier、Rubat、Coudert、Albuisson、Chopineau、Couquelet

  DOI：——

  日期：——