6-amino-3-methyl-4-(2,3,4-trimethoxy-phenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-amino-3-methyl-4-(2,3,4-trimethoxy-phenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• 英文别名: 6-amino-3-methyl-4-(2,3,4-trimethoxyphenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile；6-Amino-3-methyl-4-(2,3,4-trimethoxyphenyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• 化学式: C₁₇H₁₈N₄O₄
• 分子量: 342.354
• InChiKey: AKICUIWDLAQIDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  acetyl acetoacetate 、 丙二腈 、 2,3,4-三甲氧基苯甲醛 在 4-二甲氨基吡啶 、 hydrazine hydrate 作用下， 反应 0.33h， 以79%的产率得到6-amino-3-methyl-4-(2,3,4-trimethoxy-phenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
  参考文献：
  名称：

  Screening of a library of 4-aryl/heteroaryl-4H-fused pyrans for xanthine oxidase inhibition: synthesis, biological evaluation and docking studies

  摘要：

  A series of 4-aryl/heteroaryl-4H-fused pyrans was synthesized via multicomponent reaction in a microwave synthesizer. All the pyrans were evaluated for in vitro xanthine oxidase inhibition. Structure-activity relationship was also established. Among the series of 108 compounds, Compound 5n was the most potent displaying remarkable inhibition against the enzyme with an IC50 value of 0.59 mu M. Enzyme kinetic study was carried out for the compound 5n to determine the type of inhibition. The study revealed that the compound 5n was a mixed-type inhibitor. Molecular modelling studies were also performed to figure out the interactions of both the enantiomers of 5n with the amino acid residues of the enzyme.[GRAPHICS].

  DOI：

  10.1007/s00044-015-1382-0

文献信息

• Meglumine promoted one-pot, four-component synthesis of pyranopyrazole derivatives
  作者：Rui-Yun Guo、Zhi-Min An、Li-Ping Mo、Shu-Tao Yang、Hong-Xia Liu、Shu-Xia Wang、Zhan-Hui Zhang

  DOI：10.1016/j.tet.2013.09.082

  日期：2013.11

  catalyst for the synthesis of a series of pyranopyrazole derivatives via a one-pot, four-component reaction of carbonyl compound or isatin, hydrazine hydrate, malononitrile, and β-keto ester in EtOH–H2O. The catalyst was found to work extremely for aldehydes, ketones or isatins at room temperature to give the corresponding dihydropyrano[2,3-c]pyrazole or spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives

  证明葡甲胺是一种生物基化学物质，它是通过羰基化合物或靛红，水合肼，丙二腈和β的单锅四组分反应合成一系列吡喃并吡唑衍生物的高效且可重复使用的催化剂。酮的EtOH-H酯2 O.将催化剂在室温下发现极其对醛，酮或靛红工作以得到相应的二氢吡喃并[2,3- c ^ ]吡唑或螺[二氢吲哚-3,4'-吡喃并并[2,3- c ^ ]吡唑]衍生物以高产率。这个新方法的显着特点是广泛的底物范围，室温下的反应条件，反应时间短，产量高，容易进行后处理过程中，催化剂的可重用性，并且不存在有害的有机溶剂。
• Using magnetized water as a solvent for a green, catalyst-free, and efficient protocol for the synthesis of pyrano[2,3-c]pyrazoles and pyrano[4′,3′:5,6]pyrazolo [2,3-d]pyrimidines
  作者：Mohammad Bakherad、Ali Keivanloo、Mostafa Gholizadeh、Rahele Doosti、Mohaddese Javanmardi

  DOI：10.1007/s11164-016-2680-y

  日期：2017.2

  A facile, eco-friendly, and highly efficient one-pot four-component protocol is demonstrated for the synthesis of the pyrano[2,3-c]pyrazole and pyrano[4′,3′:5,6]pyrazolo [2,3- d ]pyrimidine derivatives using magnetized water as a new green solvent. Simplicity, short reaction time, high yield, easy work-up, and absence of hazardous organic solvents are the main advantages of this method .

  已证明一种简便，环保，高效的一锅四组分方案可用于合成吡喃并[2,3-c]吡唑和吡喃并[4'，3'：5,6]吡唑并[2， 3- d ]嘧啶衍生物，使用磁化水作为新的绿色溶剂。该方法的主要优点是操作简便，反应时间短，收率高，后处理简便且无有害有机溶剂。
• Green synthesis of pyranopyrazoles via biocatalytic one-pot Knoevenagel condensation–Michael-type addition–heterocyclization cascade in non-aqueous media
  作者：Prabhakar Shrivas、Rajat Pandey、Sangesh Zodape、Atul Wankhade、Umesh Pratap

  DOI：10.1007/s11164-020-04122-x

  日期：2020.5

  green and facile route for the one-pot four-component synthesis of pyranopyrazole derivatives through the condensation of the aromatic aldehydes, ethyl acetoacetate, malononitrile and hydrazine hydrate using baker’s yeast as biocatalyst is presented. The important aspects of the present methodology are the use of an environmentally friendly catalyst, high yield of products and mild reaction conditions,

  摘要 提出了一种高效，绿色，简便的路线，以贝克酵母作为生物催化剂，通过芳香醛，乙酰乙酸乙酯，丙二腈和水合肼的缩合，一锅四组分合成吡喃并吡唑衍生物。本方法学的重要方面是使用环境友好的催化剂，高产率的产物和温和的反应条件，即在中性pH和环境温度下。 图形摘要
• Screening of a library of 4-aryl/heteroaryl-4H-fused pyrans for xanthine oxidase inhibition: synthesis, biological evaluation and docking studies
  作者：Ramandeep Kaur、Fatima Naaz、Sahil Sharma、Samir Mehndiratta、Manish Kumar Gupta、Preet Mohinder Singh Bedi、Kunal Nepali

  DOI：10.1007/s00044-015-1382-0

  日期：2015.8

  A series of 4-aryl/heteroaryl-4H-fused pyrans was synthesized via multicomponent reaction in a microwave synthesizer. All the pyrans were evaluated for in vitro xanthine oxidase inhibition. Structure-activity relationship was also established. Among the series of 108 compounds, Compound 5n was the most potent displaying remarkable inhibition against the enzyme with an IC50 value of 0.59 mu M. Enzyme kinetic study was carried out for the compound 5n to determine the type of inhibition. The study revealed that the compound 5n was a mixed-type inhibitor. Molecular modelling studies were also performed to figure out the interactions of both the enantiomers of 5n with the amino acid residues of the enzyme.[GRAPHICS].