2-苯基-6H-吡唑并[3,4-d]哒嗪-7-酮 | 1049120-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-苯基-6H-吡唑并[3,4-d]哒嗪-7-酮
• 英文名称: 2-phenyl-2,6-dihydro-7H-pyrazolo[3,4-d]pyridazin-7-one
• 英文别名: 2-Phenyl-2H-pyrazolo[3,4-D]pyridazin-7(6H)-one；2-phenyl-6H-pyrazolo[3,4-d]pyridazin-7-one
• CAS: 1049120-92-4
• 化学式: C₁₁H₈N₄O
• mdl: MFCD11559271
• 分子量: 212.211
• InChiKey: DFBBAANEEGYHJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-苯基-6H-吡唑并[3,4-d]哒嗪-7-酮 在 tetraphosphorus decasulfide 作用下， 以 吡啶 为溶剂， 反应 4.0h， 以80%的产率得到2-phenyl-2,6-dihydro-7H-pyrazolo[3,4-d]pyridazin-7-thione
  参考文献：
  名称：

  Molecular design of pyrazolo[3,4-d]pyridazines

  摘要：

  Reactions of arenediazonium chlorides with ethyl 2-methyl-and 2-chloro-4-oxobutanoates gave, respectively, ethyl 2-(arylhydrazono)propanoates and chloro(arylhydrazono)acetates. Ethyl 2-(arylhydrazono)-propanoates reacted with the Vilsmeier-Haak reagent to give ethyl 1-aryl-4-formyl-1H-pyrazole-3-carboxylates. Ethyl 1-aryl-4-acetyl-5-methyl-1H-pyrazole-3-carboxylates were obtained by reaction of chloro(arylhydrazono) acetates with acetylacetone. Reactions of the obtained pyrazole derivatives with hydrazine and methylhydrazine led to the formation of the corresponding 3,4-R(2)(1)-6-R(2)-2-aryl-2,6-dihydro-7H-pyrazolo[3,4-d]pyridazin-7-ones (R(1), R(2) = H, Me) which were subjected to alkylation and sulfurization.

  DOI：

  10.1134/s1070428008090182
• 作为产物：
  描述：

  ethyl 4-formyl-1-phenyl-1H-pyrazole-3-carboxylate 在 肼 作用下， 生成 2-苯基-6H-吡唑并[3,4-d]哒嗪-7-酮
  参考文献：
  名称：

  Synthesis and reactions of 3-(3-ethoxycarbonyl-1-phenyl-1H-pyrazol-4-yl)propenic acid

  摘要：

  The reaction of ethyl 4-formyl-1-phenyl-1H-pyrazole-3-carboxylate with the malonic acid led to the formation (2E)-3-(3-ethoxycarbonyl-1-phenyl-1H-pyrazol-4-yl)propenic acid. In reactions of this acid chloride with 4-amino-5-aryl(hetaryl)-4H-1,2,4-triazole-3-thiols were obtained ethyl 4-[(E)-2-{3-aryl(hetaryl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl}ethenyl]-1-phenyl-1H-pyrazoe-3-carboxylates, with 5-aryltetrazoles, ethyl 4-[(E)-2-(5-aryl-1,3,4-oxadiazol-2-yl)-ethenyl]-1-phenyl-1H-pyrazole-3-carboxylates, with 1-(2-hydroxy-3,5-dimethylphenyl) followed by the Baker-Venkataraman rearrangement and the cyclization, ethyl 4-[(E)-2-(6,8-dimethyl-4-oxo-4Hchromen-2-yl)ethenyl]-1-phenyl-1H-pyrazole-3-carboxylate.

  DOI：

  10.1134/s107042800905011x

文献信息

• Discovery of a Novel Potent Tetrazole Antifungal Candidate with High Selectivity and Broad Spectrum
  作者：Tingjunhong Ni、Yumeng Hao、Zichao Ding、Xiaochen Chi、Fei Xie、Ruina Wang、Junhe Bao、Lan Yan、Liping Li、Ting Wang、Dazhi Zhang、Yuanying Jiang

  DOI：10.1021/acs.jmedchem.3c02188

  日期：2024.4.25

  exhibited potent in vitro antifungal activities against seven pathogenic fungi. Among them, tetrazole compound D2 was the most potent antifungal with MIC values of <0.008, <0.008, and 2 μg/mL against Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus, respectively, the three most common and critical priority pathogenic fungi. In addition, compound D2 also exhibited potent activity

  在前期工作的基础上，设计合成了31个新型阿巴康唑衍生物。所有化合物均对七种病原真菌表现出有效的体外抗真菌活性。其中，四唑化合物D2是最有效的抗真菌剂，其MIC值分别为<0 id=106>白色念珠菌、新型隐球菌和烟曲霉，这三种最常见和最重要的优先致病真菌。此外，化合物D2还对氟康唑耐药的耳念珠菌分离株表现出有效的活性。值得注意的是，化合物D2在体外对人 CYP450 酶表现出较低的抑制活性，对 hERG K +通道的抑制作用也较低，表明药物相互作用和 QT 延长的风险较低。此外，随着药代动力学特征的改善，化合物D2在减少真菌负荷和延长白色念珠菌感染小鼠的存活方面表现出比阿巴康唑更好的体内功效。综上所述，化合物D2将作为有希望的候选者进行进一步研究。
• Molecular design of pyrazolo[3,4-d]pyridazines
  作者：V. S. Matiichuk、M. A. Potopnyk、N. D. Obushak

  DOI：10.1134/s1070428008090182

  日期：2008.9

  Reactions of arenediazonium chlorides with ethyl 2-methyl-and 2-chloro-4-oxobutanoates gave, respectively, ethyl 2-(arylhydrazono)propanoates and chloro(arylhydrazono)acetates. Ethyl 2-(arylhydrazono)-propanoates reacted with the Vilsmeier-Haak reagent to give ethyl 1-aryl-4-formyl-1H-pyrazole-3-carboxylates. Ethyl 1-aryl-4-acetyl-5-methyl-1H-pyrazole-3-carboxylates were obtained by reaction of chloro(arylhydrazono) acetates with acetylacetone. Reactions of the obtained pyrazole derivatives with hydrazine and methylhydrazine led to the formation of the corresponding 3,4-R(2)(1)-6-R(2)-2-aryl-2,6-dihydro-7H-pyrazolo[3,4-d]pyridazin-7-ones (R(1), R(2) = H, Me) which were subjected to alkylation and sulfurization.
• Synthesis and reactions of 3-(3-ethoxycarbonyl-1-phenyl-1H-pyrazol-4-yl)propenic acid
  作者：V. S. Matiichuk、M. A. Potopnyk、N. D. Obushak

  DOI：10.1134/s107042800905011x

  日期：2009.5

  The reaction of ethyl 4-formyl-1-phenyl-1H-pyrazole-3-carboxylate with the malonic acid led to the formation (2E)-3-(3-ethoxycarbonyl-1-phenyl-1H-pyrazol-4-yl)propenic acid. In reactions of this acid chloride with 4-amino-5-aryl(hetaryl)-4H-1,2,4-triazole-3-thiols were obtained ethyl 4-[(E)-2-3-aryl(hetaryl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl}ethenyl]-1-phenyl-1H-pyrazoe-3-carboxylates, with 5-aryltetrazoles, ethyl 4-[(E)-2-(5-aryl-1,3,4-oxadiazol-2-yl)-ethenyl]-1-phenyl-1H-pyrazole-3-carboxylates, with 1-(2-hydroxy-3,5-dimethylphenyl) followed by the Baker-Venkataraman rearrangement and the cyclization, ethyl 4-[(E)-2-(6,8-dimethyl-4-oxo-4Hchromen-2-yl)ethenyl]-1-phenyl-1H-pyrazole-3-carboxylate.