6-amino-1,4-dihydro-3-methyl-4-(naphthalen-1-yl)pyrano[2,3-c]pyrazole-5-carbonitrile | 343349-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-amino-1,4-dihydro-3-methyl-4-(naphthalen-1-yl)pyrano[2,3-c]pyrazole-5-carbonitrile
• 英文别名: 6-amino-3-methyl-4-(naphthalen-1-yl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile；6-amino-3-methyl-5-cyano-4-(1-naphthayl)-1,4-dihydropyrano[2,3-c]-pyrazole；6-Amino-3-methyl-4-(1-naphthyl)-1,4-dihydropyrano[2,3-c]pyrazol-5-yl cyanide；6-amino-3-methyl-4-naphthalen-1-yl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• CAS: 343349-45-1；311326-59-7
• 化学式: C₁₈H₁₄N₄O
• 分子量: 302.335
• InChiKey: MYJZRAZFVXGFHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-amino-1,4-dihydro-3-methyl-4-(naphthalen-1-yl)pyrano[2,3-c]pyrazole-5-carbonitrile 、 N,N-二甲基甲酰胺二甲基缩醛 生成
  参考文献：
  名称：

  作为黄嘌呤氧化酶抑制剂的稠合吡喃并[3,2-d]嘧啶衍生物的合成，筛选和对接。

  摘要：

  鉴于开发有效的黄嘌呤氧化酶（XO）酶抑制剂，合成了一系列100种吡喃并[3,2-d]嘧啶衍生物，并对其体外XO酶抑制进行了评估。结构活动关系也已建立。在所有合成的化合物中，发现4d，8d和9d是最有效的酶抑制剂，IC50值分别为8μM，8.5μM和7μM。在酶动力学研究中进一步研究了化合物9d，Lineweaver-Burk图显示化合物9d是混合型抑制剂。还已经计算出最有效的化合物4d，8d和9d的分子性质。进行了对接研究以研究黄嘌呤氧化酶与最有效的XO抑制剂9d之间的识别模式。

  DOI：

  10.1016/j.ejmech.2017.03.002
• 作为产物：
  描述：

  3-甲基-3-吡唑啉-5-酮 、 2-(萘-1-基亚甲基)丙二腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以64%的产率得到6-amino-1,4-dihydro-3-methyl-4-(naphthalen-1-yl)pyrano[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

• Magnetization of biochar nanoparticles as a novel support for fabrication of organo nickel as a selective, reusable and magnetic nanocatalyst in organic reactions
  作者：Parisa Moradi、Maryam Hajjami

  DOI：10.1039/d0nj04990e

  日期：——

  and the SEM, EDS, WDX, XRD, TGA, AAS, FT-IR and VSM techniques. This magnetically recyclable catalyst was used in the homoselective synthesis of tetrazole and pyranopyrazole derivatives. This catalyst can be reused several times without significant loss of its catalytic efficiency. The heterogeneity and stability of this nanocatalyst were studied by hot filtration and the AAS technique. Also, the reused

  催化剂种类是化学，工业，医学和生物技术中的重要材料类别。同样，废物回收是绿色化学和经济效率的重要过程。因此，为了回收废物，从鸡粪中制备了生物炭纳米颗粒。然后，将生物炭纳米颗粒在绿色环保方法下磁化。最后，对磁性生物炭纳米颗粒的表面进行了修饰，然后将其用作制备镍的新型载体，该镍作为有机反应中的均选择性和可重复使用的催化剂。这种有机-无机催化剂的结构以N 2为特征吸附-解吸等温线，以及SEM，EDS，WDX，XRD，TGA，AAS，FT-IR和VSM技术。该可磁循环催化剂用于四唑和吡喃并吡唑衍生物的均选择合成。该催化剂可以重复使用几次，而不会明显降低其催化效率。通过热过滤和AAS技术研究了这种纳米催化剂的非均相性和稳定性。同样，通过SEM，EDS，AAS和BET技术对重复使用的催化剂进行了表征。
• Concentrated solar radiation-assisted one-pot/multicomponent synthesis of pyranopyrazole derivatives under neat condition
  作者：Yatin U. Gadkari、Navnath T. Hatvate、Vikas N. Telvekar

  DOI：10.1007/s11164-021-04530-7

  日期：2021.10

  Concentrated solar radiation (CSR)-assisted synthesis of pyranopyrazole derivatives under solvent and catalyst-free condition has been reported in the present protocol. One-pot multicomponent synthesis from aromatic/heteroaldehyde, ethyl acetoacetate, malononitrile, and hydrazine hydrate leads to the final desired compounds in a good yield. This operationally simple methodology has several advantages

  本协议已报道了在溶剂和无催化剂条件下集中太阳辐射 (CSR) 辅助合成吡喃并吡唑衍生物。由芳香族/杂醛、乙酰乙酸乙酯、丙二腈和水合肼一锅多组分合成，以良好的收率得到最终所需的化合物。这种操作简单的方法有几个优点，例如绿色和清洁的反应曲线、简单的后处理和纯化程序、极短的反应时间、原子效率和经济。与传统方法相比，当前的节能方法可节省近 98% 的能源。 图形概要
• 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。
• Nano silica extracted from horsetail plant as a natural silica support for the synthesis of H3PW12O40 immobilized on aminated magnetic nanoparticles (Fe3O4@SiO2-EP-NH-HPA): a novel and efficient heterogeneous nanocatalyst for the green one-pot synthesis of pyrano[2,3-c]pyrazole derivatives
  作者：Nina Hosseini Mohtasham、Mostafa Gholizadeh

  DOI：10.1007/s11164-020-04133-8

  日期：2020.6

  work, nanomesoporous silica has been prepared from horsetail (Equisetum arvense), which is a medicinal plant, with high surface area. This natural silica has been applied as a support to prepare H3PW12O40 immobilized on aminated epibromohydrin-functionalized Fe3O4@SiO2 nanoparticles (Fe3O4@SiO2-EP-NH-HPA) as a highly powerful magnetically solid acid catalyst. Characterization of this nanocatalyst has

  摘要 在这项工作中，已经从具有高表面积的药用植物马尾（Equisetum arvense）制备了纳米中孔二氧化硅。该天然二氧化硅已被用作载体，用于制备固定在胺表溴醇官能化的Fe 3 O 4 @SiO 2纳米颗粒（Fe 3 O 4 @SiO 2 -EP-NH-HPA）上的H 3 PW 12 O 40磁性固体酸催化剂。该纳米催化剂的表征已通过多种技术进行了研究，例如FTIR，XRD，N 2吸附-解吸，TEM，SEM-EDX，TGA，VSM，ICP-OES和元素分析。该磁性固体酸纳米催化剂已成功用于室温下在水性介质中一锅法合成吡喃并[2,3-c]吡唑衍生物。该方法以非常短的反应时间以优异的收率得到了结构上不同的吡喃并[2,3-c]吡唑。此外，该磁性固体酸纳米催化剂可以通过外部磁场简单地回收，并且可以连续七个反应周期重复使用而没有明显的活性损失。 图形摘要 在这项工作中，制备了Fe 3 O 4 @SiO
• Electrochemically induced one pot synthesis of 1,4-dihydropyrano[2,3- c ]-pyrazole-5-carbonitrile derivatives via a four component-tandem strategy
  作者：Abhishek Upadhyay、Laxmi Kant Sharma、Vinay K. Singh、Rahul Dubey、Narendra Kumar、Rana Krishna Pal Singh

  DOI：10.1016/j.tetlet.2017.01.049

  日期：2017.3

  An efficient one pot, multicomponent-tandem synthesis of highly functionalized 1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile is reported by electrochemically induced condensation of ethyl acetoacetate, hydrazine hydrate, malononitrile and various aromatic aldehydes. The reaction is carried out in an undivided cell, at a constant current in the presence of NaBr as a supporting electrolyte and ethanol

  通过电化学诱导乙酰乙酸乙酯，水合肼，丙二腈和各种芳香醛的电化学诱导缩合反应，可以高效地合成高官能度的1,4-二氢吡喃并[2,3- c ]-吡唑-5-腈。该反应在不分隔的电池中，在NaBr作为辅助电解质和乙醇作为溶剂的存在下，以恒定电流进行。