3-amino-5,10-dihydro-5,10-dioxo-1-propyl-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile | 1443004-28-1

• 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-5,10-dihydro-5,10-dioxo-1-propyl-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile
• 英文别名: 3-amino-1-propyl-5,10-dioxo-5,10-dihydro-1H-pyrazolo-[1,2-b]phthalazine-2-carbonitrile；3-amino-5,10-dioxo-1-propyl-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile
• CAS: 1443004-28-1
• 化学式: C₁₅H₁₄N₄O₂
• 分子量: 282.302
• InChiKey: BXGBVYSMWBKAFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-5,10-dihydro-5,10-dioxo-1-propyl-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70%的产率得到15-amino-14-propyl-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：

  邻苯二甲酰肼 、 正丁醛 、 丙二腈 在 silica gel supported tungstic acid 作用下， 以 neat (no solvent) 为溶剂， 反应 0.47h， 以89%的产率得到3-amino-5,10-dihydro-5,10-dioxo-1-propyl-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile
  参考文献：
  名称：

  Silica gel-supported tungstic acid (STA): A new, highly efficient and recyclable catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione carbonitriles and carboxylates under neat conditions

  摘要：

  摘要 1H-吡唑[1,2-b]佛尔马嗪-5,10-二酮亚硝基化合物和羧酸盐在药理学和生物学领域作为活性化合物具有广泛的应用。我们开发了一种高效且环保的硅胶载体钨酸（STA）催化一锅法合成1H-吡唑[1,2-b]佛尔马嗪-5,10-二酮亚硝基化合物和羧酸盐的方法，该方法通过醛、马龙腈/乙基氰代乙酸和佛尔马嗪在无溶剂条件下进行三组分反应。本方法的主要优点在于实验简单、使用廉价且环保的可重复使用催化剂、产率良好以及反应时间短。

  DOI：

  10.1016/j.crci.2014.01.026

文献信息

• 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。
• Ionic liquid coated sulfonated carbon@titania composites for the one-pot synthesis of indeno[1,2-b]indole-9,10-diones and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones in aqueous media
  作者：Manmeet Kour、Madhvi Bhardwaj、Harsha Sharma、Satya Paul、James H. Clark

  DOI：10.1039/c7nj00361g

  日期：——

  under aqueous conditions by creating a hydrophobic environment on the catalyst surface. The catalytic activity of the newly designed catalyst was tested in the one-pot multicomponent synthesis of indeno[1,2-b]indole-9,10-diones and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones in aqueous media. The structure of the most active catalyst, C@TiO2–SO3H–IL1, before and after the coating with the ionic liquid was

  通过将长链离子液体涂覆在磺化碳@二氧化钛复合材料上，制备了高活性和稳定的基于离子液体的新型固体布朗斯台德酸催化剂（C @ TiO 2 -SO 3 H-ILs）。离子液体涂料通过在催化剂表面形成疏水环境，在水性条件下产生了C @ TiO 2 -SO 3 H-IL的有效稳定性和活性。在一锅多组分合成茚并[1,2 - b ]吲哚-9,10-二酮和1 H-吡唑并[1,2 - b ]酞嗪-5,10中测试了新设计催化剂的催化活性。-二酮在水性介质中。活性最高的催化剂C @ TiO 2 –SO 3的结构FTIR，TGA，XRD，CHNS，EDX，SEM和HRTEM研究了离子液体包被前后的H–IL1。该催化剂可轻松回收，并具有出色的可重复使用性，最多可进行五次催化运行，而不会损失活性。