5-(4-methylphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidamide | 1318787-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-methylphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidamide
• 英文别名: 3-(4-Methylphenyl)-5-phenyl-3,4-dihydropyrazole-2-carboximidamide
• CAS: 1318787-48-2
• 化学式: C₁₇H₁₈N₄
• 分子量: 278.357
• InChiKey: ZZBZBISQLKMVIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  65.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-methylphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidamide 、 1,1,1-trifluoro-4-methoxypent-3-en-2-one 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 4-methyl-2-(3-phenyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-6-(trifluoromethyl)pyrimidine
  参考文献：
  名称：

  Straightforward and Clean Ultrasound-Promoted Synthesis of 2-(4,5-Dihydro-1H-pyrazol-1-yl)pyrimidines

  摘要：

  A series of twelve novel 2-(pyrazol-1-yl) pyrimidine derivatives was easily obtained under ultrasonic conditions by the cyclocondensation reaction of 1-carboxamidino-pyrazoles with 4-methoxyvinyl-trifluoromethyl ketones using ethanol as an environment-friendly solvent in the presence of potassium hydroxide. Comparison of the ultrasound-promoted reaction with classical methodology shows that the former is faster and gives better yield. The products were isolated in excellent purity grades without purification by chromatography or recrystalization.

  DOI：

  10.5935/0103-5053.20150078
• 作为产物：
  描述：

  3-(4-甲基苯基)-1-苯基-丙-2-烯-1-酮 、 肼甲酰亚胺酰胺一氯化氢 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 5-(4-methylphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidamide
  参考文献：
  名称：

  Anti-Candida, Anti-Enzyme Activity and Cytotoxicity of 3,5-Diaryl-4,5-dihydro-1H-pyrazole-1-carboximidamides

  摘要：

  由于需要更有效、危害更小的抗真菌疗法，以及对合成新的羧酰胺类化合物的兴趣，本研究的目标是确定一些新的吡唑羧酰胺类化合物的抗真菌和抗酶活性及其细胞毒性。为此，对提取物的最低抑菌浓度（MIC）和最低杀菌浓度（MFC）、蛋白酶和磷脂酶的产生以及细胞毒性进行了测试评估。数据分析采用方差分析和 Tukey 检验（α = 5%）。结果如下MIC 和 MFC ≥ 62.5 μg/mL（白僵菌、副丝状芽孢杆菌、法马塔芽孢杆菌、格拉布拉塔芽孢杆菌和粘膜癣菌），MIC 和 MFC ≥ 15.6 μg/mL（脂溶性芽孢杆菌）。白僵菌在接触化合物前后的蛋白酶和磷脂酶（Pz）值分别为分别为 0.6（±0.024）和 0.2（±0.022），以及 0.9（±0.074）和 0.3（±0.04）。这些蛋白酶结果不显著（p = 0.69），但磷脂酶结果显著（p = 0.01），15.6 μg/mL 是最有效的浓度。各试验的细胞毒性平均值相似（p = 0.32）。这些化合物可以作为进一步开发的模板，通过修饰或衍生物化设计出更有效的抗真菌剂。这项研究的数据证明，这些新的吡唑制剂可以作为治疗由念珠菌引起的真菌感染的替代药物。不过，仍需对这些体内和临床试验的安全性和有效性进行具体研究，以评估体外试验结果的实际意义。

  DOI：

  10.3390/molecules19055806

文献信息

• Pyrazoline based MAO inhibitors: Synthesis, biological evaluation and SAR studies
  作者：Monika Jagrat、Jagannath Behera、Samiye Yabanoglu、Ayse Ercan、Gulberk Ucar、Barij Nayan Sinha、Vadivelan Sankaran、Arijit Basu、Venkatesan Jayaprakash

  DOI：10.1016/j.bmcl.2011.05.057

  日期：2011.7

  Twenty-two pyrazoline derivatives were synthesized and tested for their human MAO (hMAO) inhibitory activity. Twelve molecules with unsubstituted ring A and substituted ring C (5–16) were found to be potent inhibitors of hMAO-A isoform with SIMAO-A in the order 103 and 104. Ten molecules with unsubstituted ring A and without ring C (21–30), in which eight molecules (21, 23–26, and 28–30) were selective

  合成了22种吡唑啉衍生物，并测试了其对人MAO（hMAO）的抑制活性。未取代的环A和取代的环C（十二分子5 - 16）被发现与SI hMAO-A同种型的强效抑制剂，MAO-A的顺序10 3和10 4。十个分子与未取代的环A和无环C（21 - 30），其中8个分子（21，23 - 26，和28 - 30）是选择性的hMAO-A，一个用于hMAO-B（22），另一1个非选择性（27）。环C的存在增加了针对hMAO-A的效力以及SI。然而，它的缺乏降低了针对hMAO-A和hMAO-B的效力和SI。
• Straightforward and Clean Ultrasound-Promoted Synthesis of 2-(4,5-Dihydro-1<i>H</i>-pyrazol-1-yl)pyrimidines
  作者：Bruna P. Kuhn、Juliana L. Malavolta、Gleison A. Casagrande、Cristiano Raminelli、Frank H. Quina、Claudio M. P. Pereira、Alex F. C. Flores、Lucas Pizzuti

  DOI：10.5935/0103-5053.20150078

  日期：——

  A series of twelve novel 2-(pyrazol-1-yl) pyrimidine derivatives was easily obtained under ultrasonic conditions by the cyclocondensation reaction of 1-carboxamidino-pyrazoles with 4-methoxyvinyl-trifluoromethyl ketones using ethanol as an environment-friendly solvent in the presence of potassium hydroxide. Comparison of the ultrasound-promoted reaction with classical methodology shows that the former is faster and gives better yield. The products were isolated in excellent purity grades without purification by chromatography or recrystalization.
• Anti-Candida, Anti-Enzyme Activity and Cytotoxicity of 3,5-Diaryl-4,5-dihydro-1H-pyrazole-1-carboximidamides
  作者：Simone Oliveira、Lucas Pizzuti、Frank Quina、Alex Flores、Rafael Lund、Claiton Lencina、Bruna Pacheco、Claudio de Pereira、Evandro Piva

  DOI：10.3390/molecules19055806

  日期：——

  Because of the need for more effective and less harmful antifungal therapies, and interest in the synthesis of new carboximidamides, the goal of this study was to determine the antifungal and anti-enzyme activities of some new pyrazole carboximidamides and their cytotoxicity. For this purpose, tests were performed to evaluate: minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC); production of proteinases and phospholipase, and cytotoxicity of the extracts. Data were analyzed by ANOVA and Tukey Tests (α = 5%). The results were: MIC and MFC ≥ 62.5 μg/mL (C. albicans, C. parapsilosis, C. famata, C. glabrata, and Rhodotorula mucillaginosa) and MIC and MFC ≥ 15.6 μg/mL (C. lipolytica). The values of proteinase and phospholipase (Pz) of C. albicans before and after exposure to the compounds were: 0.6 (±0.024) and 0.2 (±0.022) and 0.9 (±0.074) and 0.3 (±0.04), respectively. These proteinase results were not significant (p = 0.69), but those of phospholipase were (p = 0.01), and 15.6 μg/mL was the most effective concentration. The cytotoxicity means were similar among the tests (p = 0.32). These compounds could be useful as templates for further development through modification or derivatization to design more potent antifungal agents. Data from this study provide evidence that these new pyrazole formulations could be an alternative source for the treatment of fungal infections caused by Candida. However, a specific study on the safety and efficacy of these in vivo and clinical trials is still needed, in order to evaluate the practical relevance of the in vitro results.

  由于需要更有效、危害更小的抗真菌疗法，以及对合成新的羧酰胺类化合物的兴趣，本研究的目标是确定一些新的吡唑羧酰胺类化合物的抗真菌和抗酶活性及其细胞毒性。为此，对提取物的最低抑菌浓度（MIC）和最低杀菌浓度（MFC）、蛋白酶和磷脂酶的产生以及细胞毒性进行了测试评估。数据分析采用方差分析和 Tukey 检验（α = 5%）。结果如下MIC 和 MFC ≥ 62.5 μg/mL（白僵菌、副丝状芽孢杆菌、法马塔芽孢杆菌、格拉布拉塔芽孢杆菌和粘膜癣菌），MIC 和 MFC ≥ 15.6 μg/mL（脂溶性芽孢杆菌）。白僵菌在接触化合物前后的蛋白酶和磷脂酶（Pz）值分别为分别为 0.6（±0.024）和 0.2（±0.022），以及 0.9（±0.074）和 0.3（±0.04）。这些蛋白酶结果不显著（p = 0.69），但磷脂酶结果显著（p = 0.01），15.6 μg/mL 是最有效的浓度。各试验的细胞毒性平均值相似（p = 0.32）。这些化合物可以作为进一步开发的模板，通过修饰或衍生物化设计出更有效的抗真菌剂。这项研究的数据证明，这些新的吡唑制剂可以作为治疗由念珠菌引起的真菌感染的替代药物。不过，仍需对这些体内和临床试验的安全性和有效性进行具体研究，以评估体外试验结果的实际意义。