6-amino-3-methyl-4-(4-(trifluoromethyl)phenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile | 340811-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-amino-3-methyl-4-(4-(trifluoromethyl)phenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• 英文别名: 6-Amino-3-methyl-4-[4-(trifluoromethyl)phenyl]-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile；6-amino-3-methyl-4-[4-(trifluoromethyl)phenyl]-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• CAS: 340811-61-2
• 化学式: C₁₅H₁₁F₃N₄O
• 分子量: 320.274
• InChiKey: BXEODNANPYHAHP-UHFFFAOYSA-N

物化性质

• 熔点：
  244-245 °C(Solv: ethanol (64-17-5))
• 沸点：
  533.3±50.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-甲基-3-吡唑啉-5-酮 、 2-(4-三氟亚苄基)-丙二腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以51%的产率得到6-amino-3-methyl-4-(4-(trifluoromethyl)phenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
  参考文献：
  名称：

  Dihydropyrano [2,3-c] pyrazole: Novel in vitro inhibitors of yeast α-glucosidase

  摘要：

  Inhibition of alpha-glucosidase enzyme activity is a reliable approach towards controlling post-prandial hyperglycemia associated risk factors. During the current study, a series of dihydropyrano[ 2,3-c] pyrazoles (1-35) were synthesized and evaluated for their a-glucosidase inhibitory activity. Compounds 1, 4, 22, 30, and 33 were found to be the potent inhibitors of the yeast alpha-glucosidase enzyme. Mechanistic studies on most potent compounds reveled that 1, 4, and 30 were non-competitive inhibitors (K-i = 9.75 +/- 0.07, 46 +/- 0.0001, and 69.16 +/- 0.01 mu M, respectively), compound 22 is a competitive inhibitor (K-i = 190 +/- 0.016 mu M), while 33 was an uncompetitive inhibitor (K-i = 45 +/- 0.0014 mu M) of the enzyme. Finally, the cytotoxicity of potent compounds (i.e. compounds 1, 4, 22, 30, and 33) was also evaluated against mouse fibroblast 3T3 cell line assay, and no toxicity was observed. This study identifies non-cytotoxic novel inhibitors of alpha-glucosidase enzyme for further investigation as anti-diabetic agents. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2016.01.008

文献信息

• A new convenient four-component synthesis of 6-amino-2H, 4H-pyrano[2,3-c]pyrazole-5-carbonitriles and one-pot synthesis of 6 ′-amino-5-cyano-1,2-dihydrospiro-[(3H)-indole-3,4 ′-(4 ′H)-pyrano[2,3-c]pyrazol]-2-ones
  作者：Yu. M. Litvinov、L. A. Rodinovskaya、A. M. Shestopalov

  DOI：10.1007/s11172-009-0328-4

  日期：2009.11

  A new convenient method for the synthesis of 6-amino-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitriles, namely, four-component condensation of carbonyl compounds (aromatic aldehydes, heterocyclic ketones), malononitrile, β-keto esters, and hydrazine hydrate in ethanol in the presence of triethylamine as a catalyst, which occurs selectively, is developed. One-pot two-step modification of this method is proposed

  一种合成6-氨基-2H,4H-吡喃并[2,3-c]吡唑-5-腈的便捷新方法，即羰基化合物（芳香醛、杂环酮）、丙二腈、β四组分缩合在三乙胺作为催化剂存在的情况下，在乙醇中的酮酯和水合肼被开发出来，这种反应是选择性发生的。该方法的一锅两步改进用于合成螺[(3 H)-吲哚-3,4'-(4'H)-吡喃并[2,3-c]吡唑]-2-酮.
• Highly functionalized pyranopyrazoles: synthesis, antimicrobial activity, simulation studies and their structure activity relationships (SARs)
  作者：Guda Mallikarjuna Reddy、Gundala Sravya、Gutha Yuvaraja、Alexandre Camilo、Grigory V. Zyryanov、Jarem Raul Garcia

  DOI：10.1007/s11164-018-3569-8

  日期：2018.12

  the present work synthesis, simulation, and antimicrobial studies of pyranopyrazole derivatives were discussed. Among the reported compounds, 4b has dominant antimicrobial activity that was due to its higher dipole moment. Also, this compound has the most hydrophilic nature and low E g value. Besides, compound 4e has the next higher dipole moment, hydrophilic property and efficient biological activity

  摘要 有效的抗菌和抗真菌剂的开发是治疗领域中一项永恒而又不懈的研究。尽管如此，医学研究仍希望找到最好的抗菌剂。为了达到这个目的，在这里，讨论了吡喃并吡唑衍生物的当前工作合成，模拟和抗菌研究。在报告的化合物中，由于其较高的偶极矩， 4b 具有显着的抗菌活性。而且，该化合物具有最亲水的性质和较低的 E g值。此外，化合物 4e 具有更高的偶极矩，亲水性和有效的生物活性。这些结果的基本原理说明，将电子结果与生物学数据进行比较是找到有效药物化合物的更好方法。 图形概要
• Synthesis of Pyranopyrazoles under Eco-friendly Approach by Using Acid Catalysis
  作者：Guda Mallikarjuna Reddy、Jarem Raul Garcia

  DOI：10.1002/jhet.2544

  日期：2017.1

  Multicomponent synthesis of pyranopyrazole derivatives by using montmorillonite K‐10 as a reusable green acid catalyst under eco‐friendly method in the presence of eco‐friendly solvent leads to novel protocol. Moreover, catalyst could be reused five times for the reaction without noticeable loss of activity. The scope of this path was to develop new synthetic molecules by using green catalysis for further

  在环境友好型溶剂存在下，以环境友好型方法，将蒙脱土K-10用作可重复使用的绿色酸催化剂，可进行多组分合成吡喃并吡唑衍生物，从而产生了新颖的方案。而且，催化剂可重复使用五次以进行反应而没有明显的活性损失。该途径的范围是通过使用绿色催化进行进一步的筛选，例如用于有机电子材料和生物测定的起始分子，来开发新的合成分子。
• Design and development of a new functionalized cellulose-based magnetic nanocomposite: preparation, characterization, and catalytic application in the synthesis of diverse pyrano[2,3-c]pyrazole derivatives
  作者：Ali Maleki、Vahid Eskandarpour

  DOI：10.1007/s13738-019-01610-9

  日期：2019.7

  for the preparation of a new cellulose-based functionalized magnetic nanocomposite catalyst is described. The structure and morphology of the prepared nanomaterial was characterized by scanning electron microscopy, energy-dispersive X-ray analysis, X-ray diffraction patterns, and Fourier transform infrared spectroscopy analyses. Then, its catalytic activity was investigated in the synthesis of 2,4-dihydropyrano[2

  在这项工作中，描述了一种用于制备新型纤维素基功能化磁性纳米复合催化剂的简便方案。通过扫描电子显微镜，能量色散X射线分析，X射线衍射图和傅立叶变换红外光谱分析对所制备的纳米材料的结构和形态进行表征。然后，其催化活性在2,4-二氢吡喃并[2,3-的合成进行了研究Ç ]吡唑并螺[二氢吲哚-3,4'-吡喃并[2,3- Ç吡唑衍生物是通过在短反应时间，高收率和温和条件下，在靛红或醛或苯乙酮，乙酰乙酸乙酯，水合肼和丙二腈或氰基乙酸乙酯之间进行一锅四组分反应而制得的。纳米复合材料仅需通过外部磁体分离即可重复使用数次，而不会明显降低活性。
• Morpholine triflate promoted one-pot, four-component synthesis of dihydropyrano[2,3-c]pyrazoles
  作者：Chen-Feng Zhou、Jian-Jun Li、Wei-Ke Su

  DOI：10.1016/j.cclet.2016.05.010

  日期：2016.11

  Abstract A one-pot, four-component reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes, and malononitrile was discussed using Lewis acid catalyst morpholine triflate (MorT) to afford a series of dihydropyrano[2,3- c ]pyrazoles, which were generally catalyzed by organic alkalis. Moderate to excellent yields, no chromatographic purification, and evasion of environmentally hazardous solvents

  摘要利用路易斯酸催化剂吗啉三氟甲磺酸酯（MorT）讨论了乙酰乙酸乙酯，水合肼，醛和丙二腈的一锅四组分反应，制得了一系列二氢吡喃并[2,3-c]吡唑。由有机碱催化。中等至极佳的收率，无需色谱纯化，并且在反应过程中避免使用对环境有害的溶剂，因此该方案对学术界和工业界非常有用。