3-methyl-5-(4-methyl-1H-imidazol-1-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde | 1616503-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-5-(4-methyl-1H-imidazol-1-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 3-Methyl-5-(4-methylimidazol-1-yl)-1-phenyl-pyrazole-4-carbaldehyde；3-methyl-5-(4-methylimidazol-1-yl)-1-phenylpyrazole-4-carbaldehyde
• CAS: 1616503-78-6
• 化学式: C₁₅H₁₄N₄O
• 分子量: 266.302
• InChiKey: SMOQQTVNXWPDCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-5-(4-methyl-1H-imidazol-1-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 在 一水合肼 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 5-([1,1'-biphenyl]-4-yl)-3'-methyl-5'-(4-methyl-1H-imidazol-1-yl)-1'-phenyl-3,4-dihydro-1'H,2H-3,4'-bipyrazole
  参考文献：
  名称：

  Synthesis, identification and in vitro biological evaluation of some novel 5-imidazopyrazole incorporated pyrazoline and isoxazoline derivatives

  摘要：

  在本研究中，通过在乙醇中将查尔酮与水合肼和盐酸羟胺反应，合成了新型的取代吡唑啉库6a–l和异噁唑啉库7a–l。这些目标化合物被筛选以评估其对一系列致病菌株的初步体外抗菌活性、对结核分枝杆菌H37Rv的体外抗结核活性、对恶性疟原虫的体外抗疟活性，以及通过铁还原抗氧化能力法评估的体外抗氧化活性。化合物6k、6l、7h和7k表现出了优异的抗菌活性，其中一些化合物与一线药物相比表现出中等的抗结核活性。半数化合物表现出极佳的抗疟活性，而大多数化合物显示出最高的抗氧化能力。

  DOI：

  10.1039/c4nj00244j
• 作为产物：
  描述：

  依达拉奉 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-methyl-5-(4-methyl-1H-imidazol-1-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  l-脯氨酸促进新型吡唑基三氟甲基化稠合噻唑并吡喃支架的绿色和区域选择性合成及其生物学评价†

  摘要：

  一锅四组分串联型反应已要求保护一种新颖的合成吡唑基三氟甲基取代的稠合噻唑并吡喃骨架的方法。在L-脯氨酸的存在下，吡唑基醛4a-e，取代的碳硫酰胺8a-c，α-溴乙酸乙酯9和丙二腈10作为催化剂，可在较短的反应时间内以高收率得到目标产物。筛选所有化合物对一组病原菌株的初步体外抗微生物活性和对结核分枝杆菌的体外抗结核活性H37Rv。发现所有化合物对革兰氏阳性细菌枯草芽孢杆菌和破伤风杆菌都有效。一些化合物对白念珠菌显示出优异的抗真菌活性。与一线药物相比，它们中的一些还显示出中等的抗结核活性。

  DOI：

  10.1039/c4ra04283b

文献信息

• Ultrasound-assisted one-pot four-component synthesis of novel 2-amino-3-cyanopyridine derivatives bearing 5-imidazopyrazole scaffold and their biological broadcast
  作者：Piyush N. Kalaria、Shailesh P. Satasia、Jemin R. Avalani、Dipak K. Raval

  DOI：10.1016/j.ejmech.2014.06.071

  日期：2014.8

  An alternative and environmentally caring way for the synthesis of novel 2-amino-3-cyanopyridine derivatives bearing 5-imidazopyrazole nucleus is reported by one-pot four-component cyclocondensation reaction of substituted 5-(1H-imidazol/4-methyl-1-yl)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (3a-b), malononitrile (4), ammonium acetate (5) and aromatic (6a-f)/heterocyclic methyl ketones (7a-d) under ultrasonic irradiation. The newly synthesized compounds were evaluated for their in vitro antibacterial activity against a panel of pathogenic stains of bacteria and fungi, in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv stain and in vitro antioxidant activity by ferric-reducing antioxidant power method. Compounds 8e, 8h, 8l, 9c, 9g and 9h exhibited excellent antibacterial activity and compounds 3a, 8k, 9a and 9bshowed moderate antituberculosis activity as compared with the first line drugs. Majority of the compounds showed excellent antioxidant activity. This approaches claimed to be an environment friendly protocol as it afforded numerous advantages i.e. excellent yields, cleaner reaction profile and shorter reaction time.
• <scp>l</scp>-Proline promoted green and regioselective synthesis of a novel pyrazole based trifluoromethylated fused thiazolopyran scaffold and its biological evaluation
  作者：Piyush N. Kalaria、Shailesh P. Satasia、Dipak K. Raval

  DOI：10.1039/c4ra04283b

  日期：——

  A novel approach for the synthesis of a pyrazole based trifluoromethyl substituted fused thiazolopyran scaffold has been claimed by a one-pot four-component tandem type reaction. Pyrazolyl aldehydes 4a–e, substituted carbothioamide 8a–c, α-bromoethylacetate 9 and malononitrile 10 in the presence of L-proline as the catalyst yielded the targeted products in high yields over a short reaction time. All

  一锅四组分串联型反应已要求保护一种新颖的合成吡唑基三氟甲基取代的稠合噻唑并吡喃骨架的方法。在L-脯氨酸的存在下，吡唑基醛4a-e，取代的碳硫酰胺8a-c，α-溴乙酸乙酯9和丙二腈10作为催化剂，可在较短的反应时间内以高收率得到目标产物。筛选所有化合物对一组病原菌株的初步体外抗微生物活性和对结核分枝杆菌的体外抗结核活性H37Rv。发现所有化合物对革兰氏阳性细菌枯草芽孢杆菌和破伤风杆菌都有效。一些化合物对白念珠菌显示出优异的抗真菌活性。与一线药物相比，它们中的一些还显示出中等的抗结核活性。
• Synthesis, identification and in vitro biological evaluation of some novel 5-imidazopyrazole incorporated pyrazoline and isoxazoline derivatives
  作者：Piyush N. Kalaria、Shailesh P. Satasia、Dipak K. Raval

  DOI：10.1039/c4nj00244j

  日期：——

  In the present study, novel combinatorial libraries of substituted pyrazolines 6a–l and isoxazolines 7a–l have been synthesized via the reactions of chalcones with the hydrazine hydrate and hydroxylamine hydrochloride in ethanol. The title compounds were screened for their preliminary in vitro antibacterial activity against a panel of pathogenic strains, in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv, in vitro antimalarial activity against Plasmodium falciparum and in vitro antioxidant activity by the ferric-reducing antioxidant power method. Compounds 6k, 6l, 7h and 7k exhibited excellent antibacterial activity and a few of them exhibited moderate antituberculosis activity compared with the first line drugs. Half of the compounds exhibited terrific antimalarial activity and the majority of compounds showed highest antioxidant potency.

  在本研究中，通过在乙醇中将查尔酮与水合肼和盐酸羟胺反应，合成了新型的取代吡唑啉库6a–l和异噁唑啉库7a–l。这些目标化合物被筛选以评估其对一系列致病菌株的初步体外抗菌活性、对结核分枝杆菌H37Rv的体外抗结核活性、对恶性疟原虫的体外抗疟活性，以及通过铁还原抗氧化能力法评估的体外抗氧化活性。化合物6k、6l、7h和7k表现出了优异的抗菌活性，其中一些化合物与一线药物相比表现出中等的抗结核活性。半数化合物表现出极佳的抗疟活性，而大多数化合物显示出最高的抗氧化能力。