4-(1,6,11-trioxo-2,3,4,6,11,13-hexahydro-1H-indazolo[1,2-b]phthalazin-13-yl)benzonitrile | 1415214-17-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(1,6,11-trioxo-2,3,4,6,11,13-hexahydro-1H-indazolo[1,2-b]phthalazin-13-yl)benzonitrile
• 英文别名: 4-(1,6,11-Trioxo-2,3,4,13-tetrahydroindazolo[1,2-b]phthalazin-13-yl)benzonitrile
• CAS: 1415214-17-3
• 化学式: C₂₂H₁₅N₃O₃
• 分子量: 369.379
• InChiKey: VGHWJVFZJZHZOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  81.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯酐 、 1,3-环己二酮 、 4-氰基苯甲醛 在 一水合肼 作用下， 反应 0.25h， 以92%的产率得到4-(1,6,11-trioxo-2,3,4,6,11,13-hexahydro-1H-indazolo[1,2-b]phthalazin-13-yl)benzonitrile
  参考文献：
  名称：

  Solvent-free, one-pot, four-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones using sulfuric acid-modified PEG-6000 as a green recyclable and biodegradable polymeric catalyst

  摘要：

  A green practical method for the efficient synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-triones using sulfuric acid-modified polyethylene glycol-6000 (PEG-OSO3H) as an eco-friendly polymeric catalyst from the four-component condensation reaction of phthalic anhydride, hydrazinium hydroxide, 1,3-cyclohexanedione or 5,5-dimethyl 1,3-cyclohexanedione (dimedone) and aromatic aldehydes under solvent-free conditions at 80 degrees C is described. This approach allowed the environmental impact factor (E-factor) to be minimized. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.cattod.2012.05.026

文献信息

• Introduction of O-sulfonated poly(vinylpyrrolidonium) hydrogen sulfate as an efficient, and reusable solid acid catalyst for some solvent-free multicomponent reactions
  作者：Omid Goli-Jolodar、Farhad Shirini、Mohadeseh Seddighi

  DOI：10.1039/c6ra08486a

  日期：——

  In this work, O-sulfonated poly(vinylpyrrolidonium) hydrogen sulphate has been prepared as a powerful recyclable solid acid catalyst and characterized using a variety of techniques including elemental analysis, FT-IR, TGA, SEM, XRD, pH analysis and Hammett acidity function.

  在这项工作中，已制备了O-磺化的聚（乙烯基吡咯烷酮）硫酸氢盐，它是一种功能强大的可循环使用的固体酸催化剂，并使用多种技术进行了表征，包括元素分析，FT-IR，TGA，SEM，XRD，pH分析和Hammett酸度函数。
• <scp> 2 <i>H</i> ‐Indazolo </scp> [2,1‐ <i>b</i> ]phthalazine‐trione derivatives: Inhibition on some metabolic enzymes and molecular docking studies
  作者：Parham Taslimi、Fikret Türkan、Kadir Turhan、Halide Sedef Karaman、Zuhal Turgut、İlhami Gulcin

  DOI：10.1002/jhet.4019

  日期：2020.8

  aromatic aldehydes, cyclic 1,3‐dione, and phthalhydrazide in ethanol catalyzed by Y(OTf)3 showed satisfactory inhibitory effects against some important enzymes. Also, these molecules had Ki values in the row of 185.92 ± 36.03‐294.82 ± 50.76 nM vs carbonic anhydrase I (CA I), 204.93 ± 46.90‐374.10 ± 83.63 nM against human CA II, 937.16 ± 205.82‐1021.83 ± 193.66 nM against α‐glycosidase (α‐Gly), respectively

  在这项研究中，取代的2H-吲哚并[ 2,1- b ]酞嗪-1,6,11-三酮化合物（4a-d）是通过芳香醛，环状1,3-二酮的一锅三组分缩合反应获得的，Y（OTf）3催化乙醇中的邻苯二甲酰肼显示出对某些重要酶的令人满意的抑制作用。同样，这些分子相对于碳酸酐酶I（CA I）的行中的K i值为185.92±36.03-294.82±50.76 nM，针对人CA II的204.93±46.90-374.10±83.63 nM，937.16±205.82-11021.83±193.66 nM分别针对α-糖苷酶（α-Gly）。对于胆碱酯酶，K i抗乙酰胆碱酯酶（AChE）的值分别为47.26±9.62-72.05±19.47 nM和抗丁酰胆碱酯酶（BChE）的范围为65.03±9.88-102.83±25.04 nM。比较了这些化合物对名称为AChE，BChE，α-Gly，hCA I和hCA II的
• Introduction of a Novel Nano Sized <i>N</i>-Sulfonated Brönsted Acidic Homogeneous Catalyst for the Promotion of the Synthesis of 2<i>H</i>-Indazolo[2,1-<i>b</i>]Phthalazine-1,6,11(13<i>H</i>)-Triones
  作者：Omid Goli-Jolodar、Farhad Shirini、Mohadeseh Seddighi

  DOI：10.1166/jnn.2018.13922

  日期：2018.1.1

  In this research work, 4,4'-(butane-1,4-diyl) bis(1-sulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium) tetrachloride (NS-C4(DABCO-SO3H)(2)center dot 4Cl) as a new nano-sized N-sulfonic acid was prepared and characterized using different types of spectroscopic methods including FT-IR, H-1 NMR, C-13 NMR, XRD, TGA and SEM analysis. This new reagent was efficiently used as catalyst for the promotion of the one-pot synthesis of 2H-indazolo[2,1-b] phthalazine-1,6,11(13H)-triones derivatives, as a class of biologically active compounds with important pharmaceutical properties, under solvent-free conditions during short reaction times in high yields.
• Efficient One-Pot Synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11-trione Derivatives Catalyzed by Y(OTf)3
  作者：K. Turhan、Z. Turgut

  DOI：10.1134/s1070428019020180

  日期：2019.2

  In this study, substituted 2H-indazolo[2,1-b]phthalazine-1,6,11-triones, that may possess biological activity, have been synthesized via one-pot three-component cyclocondensation reaction of aromatic aldehydes, cyclic 1,3-dione and phthalhydrazide in ethanol catalyzed by Y(OTf)(3) with good to excellent yields. The structures of all synthesized compounds, 3,4-dihydro-13-phenyl-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione (4a), 13-(4-cyanophenyl)-3,4-dihydro-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione (4b), 3,4-dihydro-3,3-dimethyl-13-(4-cyanophenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione (4c), 3,4-dihydro-3,3-dimethyl-13-phenyl-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione (4d), and 3,4-dihydro-13-(4-isopropylphenyl)-3,3-dimethyl-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione (4e) have been elucidated from IR, NMR and mass spectral data.