6-<4-benzyl-1-piperazinyl>-3(2H)-pyridazinone | 145276-62-6

• 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: 6-<4-benzyl-1-piperazinyl>-3(2H)-pyridazinone
• 英文别名: 6-(4-Benzylpiperazin-1-yl)pyridazin-3-ol；3-(4-benzylpiperazin-1-yl)-1H-pyridazin-6-one
• CAS: 145276-62-6
• 化学式: C₁₅H₁₈N₄O
• 分子量: 270.334
• InChiKey: XRBIDNDPWPZTIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-<4-benzyl-1-piperazinyl>-3(2H)-pyridazinone 在 盐酸 、 4-二甲氨基吡啶 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 13.0h， 生成 3-[3-(4-benzylpiperazin-1-yl)-6-oxopyridazin-1(6H)-yl]-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)propanamide
  参考文献：
  名称：

  Synthesis of antipyrine/pyridazinone hybrids and investigation of their in vivo analgesic and anti-inflammatory activities

  摘要：

  合成了 11 种抗吡啶/哒嗪酮杂交化合物，并分别通过对苯醌诱导的蠕动试验和卡拉胶诱导的爪水肿模型对其体内镇痛和抗炎活性进行了评估。 试验结果表明，与阿司匹林和吲哚美辛相比，化合物 6a、6c 和 6d 分别具有相同或更强的镇痛和抗炎作用。研究还考察了化合物对胃黏膜的副作用。 在测试条件下，发现大多数化合物都不会引起溃疡。

  DOI：

  10.3906/kim-1111-29
• 作为产物：
  描述：

  3-(4-苄基哌嗪-1-基)-6-氯哌嗪 在 溶剂黄146 作用下， 反应 6.0h， 生成 6-<4-benzyl-1-piperazinyl>-3(2H)-pyridazinone
  参考文献：
  名称：

  Synthesis of antipyrine/pyridazinone hybrids and investigation of their in vivo analgesic and anti-inflammatory activities

  摘要：

  合成了 11 种抗吡啶/哒嗪酮杂交化合物，并分别通过对苯醌诱导的蠕动试验和卡拉胶诱导的爪水肿模型对其体内镇痛和抗炎活性进行了评估。 试验结果表明，与阿司匹林和吲哚美辛相比，化合物 6a、6c 和 6d 分别具有相同或更强的镇痛和抗炎作用。研究还考察了化合物对胃黏膜的副作用。 在测试条件下，发现大多数化合物都不会引起溃疡。

  DOI：

  10.3906/kim-1111-29

文献信息

• Synthesis and Analgesic and Antiinflammatory Activity of Methyl 6-Substituted-3(2H)-pyridazinone-2-ylacetate Derivatives
  作者：M. F. Şahina、B. Badıçoglu、M. Gökçe、E. Küpeli、E. Yeşilada

  DOI：10.1002/ardp.200400896

  日期：2004.8

  reference nonsteroidal anti‐inflammatory drugs. Methyl 6‐(4‐(4‐fluorophenyl)piperazine)‐3(2H)‐pyridazinone‐2‐ylacetate 9e was found to be more active than acetylsalicylic acid (ASA). Methyl 6‐(4‐(2‐ethoxyphenyl)piperazine)‐3(2H)‐pyridazinone‐2‐ylacetate 9c has shown an anti‐inflammatory activity as compared to the standard compound indometacin at the carrageenan‐induced paw edema method.

  合成了一系列甲基6-取代-3(2H)-哒嗪酮-2-乙酰乙酸酯9，并在苯基苯醌诱导的扭体试验（PBQ试验）和角叉菜胶诱导的爪水肿法中评估了它们的镇痛和抗炎作用，分别。检查了化合物对胃粘膜的副作用。与参考非甾体抗炎药相比，没有一种化合物显示出胃溃疡作用。发现 6-(4-(4-氟苯基)哌嗪)-3(2H)-哒嗪酮-2-基乙酸酯 9e 比乙酰水杨酸 (ASA) 更具活性。与标准化合物吲哚美辛相比，6-(4-(2-乙氧基苯基)哌嗪)-3(2H)-哒嗪酮-2-基乙酸酯 9c 在角叉菜胶诱导的爪水肿方法中显示出抗炎活性。
• Design and synthesis of pyridazinone-based 5-HT2C agonists
  作者：Charlotte M.N. Allerton、Mark D. Andrews、Julian Blagg、David Ellis、Edel Evrard、Martin P. Green、Kevin K.-C. Liu、Gordon McMurray、Michael Ralph、Vivienne Sanderson、Robin Ward、Lesa Watson

  DOI：10.1016/j.bmcl.2009.07.136

  日期：2009.10

  The SAR of a series of pyridazinone derived 5-HT2C agonists has been explored and resulted in identification of a compound with excellent levels of 5-HT2C functional agonism and selectivity over 5-HT2A and 5-HT2B. This compound displayed good in vivo efficacy in pre-clinical models of stress urinary incontinence, despite having physiochemical properties commensurate with impaired CNS penetration. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and pharmacological activity of some new pyridazinones
  作者：S Corsano、G Strappaghetti、A Codagnone、R Scapicchi、G Marucci

  DOI：10.1016/0223-5234(92)90189-8

  日期：1992.8

  The synthesis of a series of piperazinyl-pyridazinones is reported. The blocking activity of these compounds was determined on the pre- and postsynaptic alpha-adrenoreceptors of isolated rat vas deferens. For compounds 7, 17 and 18, the hypotensive activity was also evaluated.
• Synthesis and antinociceptive activity of 6-substituted-3-pyridazinone derivatives
  作者：Mehtap Gokçe、Deniz Dogruer、Mustafa Fethi Sahin

  DOI：10.1016/s0014-827x(01)01037-0

  日期：2001.4

  A series of 3-pyridazinones carrying morpholino, arylpiperidino and arylpiperazino moiety in the position 6 IIa-g were synthesized and evaluated for antinociceptive activity. In the modified Koster test in mice 4-(4-fluorophenyl) piperazine, IIf, was found the most active compound. All the compounds except IId were more active than aspirin in the antinociceptive activity test. (C) 2001 Elsevier Science S.A. All rights reserved.
• Synthesis of antipyrine/pyridazinone hybrids and investigation of their in vivo analgesic and anti-inflammatory activities
  作者：SULTAN BAYTAŞ、NAZAN İNCELER、KHATEREH FATTAHPOUR MAVANEH、MECİT ORHAN ULUDAĞ、NURETTİN ABACIOĞLU、MEHTAP GÖKÇE

  DOI：10.3906/kim-1111-29

  日期：——

  Eleven antipyrine/pyridazinone hybrids were synthesized and evaluated for their in vivo analgesic and anti-inflammatory activities by p-benzoquinone-induced writhing test and carrageenan-induced paw edema model, respectively. The test results indicated that compounds 6a, 6c, and 6d were equally or more potent analgesic and anti-inflammatory agents than aspirin and indomethacin, respectively. Side effects of the compounds were examined on gastric mucosa. Most of the compounds were found to be non-ulcerogenic under test conditions.

  合成了 11 种抗吡啶/哒嗪酮杂交化合物，并分别通过对苯醌诱导的蠕动试验和卡拉胶诱导的爪水肿模型对其体内镇痛和抗炎活性进行了评估。 试验结果表明，与阿司匹林和吲哚美辛相比，化合物 6a、6c 和 6d 分别具有相同或更强的镇痛和抗炎作用。研究还考察了化合物对胃黏膜的副作用。 在测试条件下，发现大多数化合物都不会引起溃疡。