3-amino-1-(2-fluorophenyl)-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile | 1443004-17-8

• 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-fluorophenyl)-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile
• 英文别名: 3‑amino‑1‑(2‑fluorophenyl)‑5,10‑dihydro‑5,10‑dioxo‑1H‑pyrazolo[1,2‑b]phthalazine‑2‑carbonitrile；3-amino-1-(2-fluorophenyl)-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile
• CAS: 1443004-17-8
• 化学式: C₁₈H₁₁FN₄O₂
• 分子量: 334.309
• InChiKey: MOONDBMYNAIBCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 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：
  90.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-amino-1-(2-fluorophenyl)-5,10-dihydro-5,10-dioxo-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80%的产率得到15-amino-14-(2-fluorophenyl)-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：

  苯酐 在 hydrazine hydrate 作用下， 以 neat (no solvent) 为溶剂， 反应 1.08h， 生成 3-amino-1-(2-fluorophenyl)-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile
  参考文献：
  名称：

  纳米磁性苯并-1,3-二磺酸哌啶鎓离子液体的制备，表征，新型，绿色和多相催化剂及其在合成1H-吡唑并[1,2-b]酞嗪-5,10-二酮和1H-中的应用吡唑并[1,2-a]哒嗪-5,8-二酮在无溶剂条件下

  摘要：

  1 H-吡唑并[1,2- b ]酞嗪-5,10-二酮和1 H-吡唑并[1,2- a的一锅四组分合成]哒嗪-5,8-二酮是在无溶剂条件下于110°C下使用哌啶苯-1,3-二磺酸盐纳米磁性离子液体（由各种醛，丙二腈，水合肼和邻苯二甲酸酐或顺丁烯二酸酐之间的反应进行的）制得的NMIL）作为一种新型且可重复使用的催化剂。所提出的方法的一些优点是成本的显着降低，有效的催化作用和催化剂的可重复使用性。使用傅里叶变换红外光谱，X射线衍射，扫描和透射电子显微镜，热重分析，导数热重分析，Brunauer-Emmett-Teller分析，振动样品磁力分析和能量分散X射线光谱对NMIL进行了全面表征。该技术是一种适合合成1 H的安全方法-吡唑并[1,2- b ]酞嗪-5,10-二酮和1 ħ -吡唑并[1,2一]哒嗪-5,8-二酮利用一个高效的和可重复使用的绿色催化剂。

  DOI：

  10.1002/aoc.3717

文献信息

• A convenient approach for the synthesis of various derivatives of pyrazolo[1,2-b]phthalazinediones in the presence of an efficient supported basic ionic liquid at ambient temperature and solvent-free media
  作者：Fereshteh Hatami Sabour、Mahboobeh Nasr-Esfahani、Iraj Mohammadpoor-Baltork、Shahram Tangestaninejad、Majid Moghadam、Valiollah Mirkhani

  DOI：10.1007/s13738-017-1267-x

  日期：2018.3

  benzoyl-substituted pyrazolo[1,2-b]phthalazinediones in high yields. Moreover, selective synthesis of mono- and bis-pyrazolo[1,2-b]phthalazinediones from dialdehydes was investigated in this approach. The catalyst could be easily separated by an external magnet and reused seven times without any significant loss of activity. Graphical AbstractAn efficient procedure is described for one-pot synthesis of various cyano-

  摘要已经描述了一种方便的方法，用于在环境温度和无溶剂介质下一锅合成各种吡唑并[1,2- b ]酞嗪二酮。首先，制备了一种新型的负载型碱性离子液体（[SiPMIM] OH @ MNPs），并通过FT-IR，元素分析，VSM，SEM，TEM和XRD对其进行了表征。该催化剂在芳族醛，邻苯二甲酰肼和丙二腈（或无环1,3-二羰基化合物）的一锅反应中显示出优异的催化活性，可提供高氰基，乙酰基或苯甲酰基取代的吡唑并[1,2- b ]邻苯二甲二酮。产量。此外，单-和双-吡唑并[1,2- b的选择性合成用这种方法研究了来自二醛的邻苯二甲酮二酮。该催化剂可以很容易地被外部磁体分离，并且可以重复使用七次而活性没有明显损失。 图形概要描述了一种在[SiPMIM] OH @ MNPs存在下于环境温度和无溶剂条件下一锅合成各种氰基，乙酰基或苯甲酰基取代的吡唑并[1,2- b ]邻苯二甲二酮的有效方法。
• 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。
• InCl3-catalyzed green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones under solvent-free conditions
  作者：Mudumala Veeranarayana Reddy、Yeon Tae Jeong

  DOI：10.1016/j.tetlet.2013.04.109

  日期：2013.7

  A simple, efficient, and green practical approach to 1H-pyrazolo[1,2-b]phthalazine-5,10-diones from phthalhydrazide, aldehydes, and malononitrile/ethyl cyanoacetate has been developed that uses inexpensive and readily available InCl3 as a catalyst in solvent-free one-pot three-component cyclo condensation reaction. This method should provide high yields, shorter reaction time, easy work-up, purification

  已开发出一种简单，有效且绿色的实用方法，用于从邻苯二甲酰肼，醛和丙二腈/氰基乙酸乙酯中合成1 H-吡唑并[1,2- b ]邻苯二甲-5,10-二酮，使用廉价且易得的InCl 3作为无溶剂一锅三组分环缩合反应中的催化剂。该方法应提供高收率，较短的反应时间，易于后处理，通过非色谱法纯化产物以及更清洁的反应。这是N-稠合杂环合成的新策略，在有机和药物化学中具有更广泛的应用。
• β-Cyclodextrin as a Supramolecular Catalyst for the Synthesis of 1H-Pyrazolo[1,2-b]phthalazine-5,10-dione Derivatives in Water
  作者：Yogesh A. Tayade、Dipak S. Dalal

  DOI：10.1007/s10562-017-2032-6

  日期：2017.6

  An efficient and green method has been developed for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones derivatives by employing 20 mol% β-cyclodextrin via a one-pot multicomponent reaction of aldehydes, malononitrile and phthalhydrazide in H2O–EtOH (4:1) at 100 °C for first time under neutral condition. The catalyst could be recovered and reused for four consecutive cycles without appreciable

  开发了一种高效、绿色的合成 1H-吡唑并[1,2-b]酞嗪-5,10-二酮衍生物的方法，采用 20 mol% β-环糊精，通过醛、丙二腈和丙二腈的一锅多组分反应合成 1H-吡唑并[1,2-b]酞嗪-5,10-二酮衍生物。邻苯二甲酰肼在 H2O–EtOH (4:1) 中在 100 °C 下首次在中性条件下进行。该催化剂可以回收并重复使用四个连续循环而催化活性没有明显损失。图形摘要
• Theophylline as a Green Catalyst for the Synthesis of 1<i>H</i>-Pyrazolo[1,2-b]phthalazine-5,10-diones
  作者：Farzaneh Mohamadpour

  DOI：10.1080/00304948.2019.1697611

  日期：2020.1.2

  1H-Pyrazolo[1,2-b]phthalazine-5,10-diones are a significant class of heterocyclic compounds and represent an interesting template in medicinal chemistry. Many of these compounds are known for their...

  1H-Pyrazolo[1,2-b]phthalazine-5,10-diones 是一类重要的杂环化合物，是药物化学中一个有趣的模板。许多这些化合物以其...