3-amino-1-(2-nitrophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile | 1206604-84-3

• 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: 3-amino-1-(2-nitrophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile
• 英文别名: 3-amino-1-(2-nitrophenyl)-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile；3-amino-1-(2-nitrophenyl)-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile
• CAS: 1206604-84-3
• 化学式: C₁₈H₁₁N₅O₄
• 分子量: 361.316
• InChiKey: WYNJYRRQVQZUQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-amino-1-(2-nitrophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile 、 环己酮 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以85%的产率得到15-amino-14-(2-nitrophenyl)-2,3,4,14-tetrahydro-1H-quinolino[2',3':3,4]pyrazolo[1,2-b]phthalazine-7,12-dione
  参考文献：
  名称：

  New racemic annulated pyrazolo[1,2-b]phthalazines as tacrine-like AChE inhibitors with potential use in Alzheimer's disease

  摘要：

  A novel series of tacrine-like compounds 7a-u possessing a fused pyrazolo[1,2-b]phthalazine structure were designed and synthesized as potent and selective inhibitors of AChE. The in-vitro biological assessments demonstrated that several compounds had high anti-AChE activity at nano-molar level. The more promising compound 71 with IC50 of 49 nM was 7-fold more potent than tacrine and unlike tacrine, it was highly selective against AChE over BuChE. The cell-based assays against hepatocytes (HepG2) and neuronal cell line (PC12) revealed that 71 had significantly lower hepatotoxicity compared to tacrine, with additional neuroprotective activity against H2O2-induced damage in PC12 cells. This compound could also inhibit AChE-induced and self-induced A beta peptide aggregation. The advantages including synthetic accessibility, high potency and selectivity, low toxicity, adjunctive neuroprotective and A beta aggregation inhibitory activity, make this compound as a new multifunctional lead for Alzheimer's disease drug discovery. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.07.072
• 作为产物：
  描述：

  邻苯二酰胺 在 hydrazine hydrate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 1.4h， 生成 3-amino-1-(2-nitrophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile
  参考文献：
  名称：

  H4 [W12SiO40]的纳米磁异化反应：用于1H-吡唑并[1,2-b]邻苯二甲二酮衍生物的合成

  摘要：

  我们方便地在氨基官能化的硅磁铁矿纳米粒子上涂覆硅钨酸（STA，H 4 [W 12 SiO 40 ]），因为磁性纳米粒子的表面官能化是绿色高效催化的绝佳方法。使用各种技术对纳米颗粒进行结构表征。通过合成1 H –吡唑并[1,2- b]探测了STA-胺-Si-磁铁矿纳米颗粒的催化活性和可回收性]酞嗪二酮衍生物。反应平稳进行，以优异的产率和短的反应时间提供产物。可以使用简单的外部磁体轻松回收催化剂，并重复使用几次，而不会造成活性的任何损失。在此，我们报告了作为均相和非均相催化剂的H 4 [W 12 SiO 40 ]的活性的比较，发现后者更为有效。这些发现为吡唑并[1,2- b ]邻苯二甲腈二酮衍生物的环境友好合成提供了有效的方法。

  DOI：

  10.1002/aoc.4001

文献信息

• Mild preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives with magnetic Fe3O4 nanoparticles coated by (3-aminopropyl)-triethoxysilane as catalyst under ambient and solvent-free conditions
  作者：Hamid Reza Shaterian、Majid Mohammadnia

  DOI：10.1007/s11164-012-0969-z

  日期：2014.1

  An efficient, one-pot quantitative procedure for preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives from four-component condensation reaction of hydrazine monohydrate, phthalic anhydride, malononitrile or ethyl cyanoacetate, and aromatic aldehydes in the presence of magnetic Fe3O4 nanoparticles coated by (3-aminopropyl)-triethoxysilane as catalyst under mild, ambient, and solvent-free conditions is described. Simple procedure, high yield, short reaction time, and environmentally benign method are advantages of this protocol. The magnetic Fe3O4 nanoparticles coated by (3-aminopropyl)-triethoxysilane can be recovered and reused several times without loss of activity.

  描述了一种高效的一锅法定量制备1H-吡唑并[1,2-b]酞嗪-5,10-二酮衍生物的方法，该方法通过水合肼、邻苯二甲酸酐、丙二腈或氰乙酸乙酯与芳香醛在磁性Fe3O4纳米粒子（表面包覆有(3-氨丙基)-三乙氧基硅烷）催化下进行四组分缩合反应，条件温和、环境、无溶剂。该方案的优点是操作简单、产率高、反应时间短、环境友好。磁性Fe3O4纳米粒子（表面包覆有(3-氨丙基)-三乙氧基硅烷）可回收并重复使用多次而不会丧失活性。
• Preparation of 1<i>H</i>-pyrazolo[1,2-<i>b</i>]phthalazine-5,10-diones using ZrO₂ nanoparticles as a catalyst under solvent-free conditions
  作者：Mohammad Piltan

  DOI：10.1515/hc-2017-0142

  日期：2017.10.26

  Abstract Zirconium oxide nanoparticles are an efficient catalyst for the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones via a three-component reaction of phthalhydrazide, aromatic aldehydes and malononitrile under solvent-free conditions.

  摘要 氧化锆纳米颗粒是一种有效的催化剂，可在无溶剂条件下通过邻苯二甲酰肼、芳香醛和丙二腈的三组分反应制备 1H-吡唑并[1,2-b]酞嗪-5,10-二酮。
• Nano Brönsted solid acid containing double-charged diazoniabi-cyclo[2.2.2]octane chloride supported on nano rice husk silica: an efficient catalyst for the one-pot synthesis of phthalazine compounds
  作者：Jamal Davarpanah、Ali Reza Kiasat

  DOI：10.1039/c4ra13263g

  日期：——

  (TGA-DTG), and Brunauer–Emmett–Teller (BET) measurements. The catalytic activity of this nanocomposite was successfully tested through the one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones via three-component couplings of phthalhydrazide, aromatic aldehydes, and malononitrile. The heterogeneous catalyst could be recovered easily and reused without significant loss of its catalytic activity

  在目前的工作中，从低成本稻壳灰（RH-SiO 2）合成了无定形二氧化硅纳米粒子。纳米粒子随后通过溶胶-凝胶法（RH @ [SiPrDABCO @ BuSO 3 H] HSO 4）用含有双电荷的重氮二氮杂双环[2.2.2]辛烷的酸性离子液体改性。通过傅立叶变换红外光谱（FT-IR），扫描电子显微镜（SEM），热重分析-导数热重分析（TGA-DTG）和Brunauer-Emmett-Teller（BET）对这一布朗斯台德固体酸的结构性质进行了系统研究） 测量。通过一锅合成1 H-吡唑并[1,2- b]成功地测试了该纳米复合材料的催化活性。通过邻苯二甲酰肼，芳族醛和丙二腈的三组分偶联反应制得] phthalazine-5,10-diones 。该多相催化剂可以容易地回收和再利用而不会显着损失其催化活性。
• New role for photoexcited organic dye, Na2 eosin Y via the direct hydrogen atom transfer (HAT) process in photochemical visible-light-induced synthesis of spiroacenaphthylenes and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones under air atmosphere
  作者：Farzaneh Mohamadpour

  DOI：10.1016/j.dyepig.2021.109628

  日期：2021.10

  A green multi-component tandem strategy for metal-free synthesizing spiroacenaphthylenes and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones by Knoevenagel-Michael cyclocondensation is reported via organic dye Na2 eosin Y-derived photoexcited states functions as a direct hydrogen atom transfer (HAT) catalyst via visible light-mediated in aqueous ethyl lactate at ambient temperature under air atmosphere.

  通过有机染料 Na 2曙红 Y 衍生的光激发态，通过Knoevenagel-Michael 环缩合反应无金属合成螺苊和 1 H-吡唑并[1,2 - b ]酞嗪-5,10-二酮的绿色多组分串联策略在环境温度和空气气氛下，通过可见光介导的乳酸乙酯水溶液作为直接氢原子转移 (HAT) 催化剂。这项研究为进一步使用具有商业可用性和廉价性的无金属有机染料 Na 2曙红Y在光化学合成中使用最少的催化剂，能源效率高，收率高，操作简单，反应省时，原子经济性高，从而满足可持续和绿色化学的一些特征。值得注意的是，这种环化反应也可以在克级规模上运行，这凸显了该反应在工业用途中的潜力。
• Mild basic ionic liquids catalyzed new four-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones
  作者：Hamid Reza Shaterian、Majid Mohammadnia

  DOI：10.1016/j.molliq.2012.06.007

  日期：2012.9

  A new four-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives using three weak basic ionic liquids such as 1,8-diazabicyclo[5.4.0]-undec-7-en-8-ium acetate, pyrrolidinium formate, and pyrrolidinium acetate as efficient catalysts for condensation reaction of hydrazine monohydrate, phthalic anhydride, malononitrile or ethyl cyanoacetate, and aromatic aldehydes under ambient and

  使用三种弱碱性离子液体，例如1,8-二氮杂双环[5.4.0] -undec-7-en，由1 H-吡唑并[1,2-b]酞嗪-5,10-二酮衍生物组成的新的四组分合成方法描述了在环境温度和无溶剂条件下，一水合肼，邻苯二甲酸酐，丙二腈或氰基乙酸乙酯与芳族醛的缩合反应的高效催化剂，乙酸-8-铵，甲酸吡咯烷鎓盐和乙酸吡咯烷鎓盐具有优异的收率。