3,3-dimethyl-7-nitro-9-phenyl-3,4-dihydroacridin-1(2H)-one | 871322-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,3-dimethyl-7-nitro-9-phenyl-3,4-dihydroacridin-1(2H)-one
• 英文别名: 3,3-Dimethyl-7-nitro-9-phenyl-2,4-dihydroacridin-1-one
• CAS: 871322-19-9
• 化学式: C₂₁H₁₈N₂O₃
• 分子量: 346.386
• InChiKey: JYPYYKNQRVHZPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl-7-nitro-9-phenyl-3,4-dihydroacridin-1(2H)-one 在 sodium methylate 、 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 8.0h， 生成 4,4-dimethyl-9-nitro-11-phenyl-4,5-dihydro-2H-pyrazolo[3,4-a]acridine
  参考文献：
  名称：

  Efficient Protocol for Synthesis of Pyrazolo[3,4-a]acridines

  摘要：

  A new class of pyrazolo[3,4-a]acridines have been prepared. The synthon acridones were obtained in very good yield by a one-pot reaction of 2-amino-5-chloro or nitro substituted benzophenones with 1,3-cyclic diketones in the presence of freshly prepared Eaton's reagent without solvent, using Friedlander synthesis. The intermediates were reacted with ethylformate followed by hydrazine hydrate to afford pyrazolo[3,4-a]acridines. All of the compounds were purified by recrystallization only, and no chromatographic workup was required. The structures of the synthesized compounds were deduced by spectroscopic techniques, including single-crystal x-ray diffraction.

  DOI：

  10.1080/00397911.2015.1070433
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 2-氨基-5-硝基二苯甲酮 在 sulfated polyborate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.33h， 以91%的产率得到3,3-dimethyl-7-nitro-9-phenyl-3,4-dihydroacridin-1(2H)-one
  参考文献：
  名称：

  硫酸化聚硼酸酯催化选择性 Friedlander 环化合成高度官能化的喹啉

  摘要：

  由于其广泛的生物活性，喹啉部分是一种特殊的支架。1 , 2 与 Friedlander 环化法一起，开发了用于合成……的其他程序。

  DOI：

  10.1080/00304948.2020.1762457

文献信息

• Nickel nanoparticles: a highly efficient and retrievable catalyst for the solventless Friedlander annulation of quinolines and their in silico molecular docking studies as histone deacetylase inhibitors
  作者：Gangadhara Angajala、Radhakrishnan Subashini

  DOI：10.1039/c5ra06593c

  日期：——

  environmental friendly, green, solvent-free protocol for the preparation of polysubstituted quinolines via Friedlander annulation using nickel nanoparticles (80–100 nm) biofabricated from Aegle Marmelos Correa aqueous leaf extract. These nickel nano materials exhibit high catalytic efficacy to achieve the target molecules in excellent yields ranging from 85–96% mainly due to their diverse properties

  本工作探索了一种高效，环保，绿色，无溶剂的方案，该方案通过使用从Aegle Marmelos Correa水性叶片提取物中生物制造的镍纳米粒子（80–100 nm），通过弗里德兰德法制得多取代喹啉。这些镍纳米材料显示出高催化效率，以优良的收率（85-96％）可实现目标分子，这主要是由于它们具有多种多样的特性以及高的表面积体积比。FT-IR，1 H NMR，13成功表征了合成的多取代喹啉1 H NMR和GC-MS。已经研究了各种溶剂和催化剂浓度对喹啉合成的影响，其中在无溶剂条件下，以镍纳米催化剂的10mol％获得高产率的产物。该催化剂在无溶剂条件下可在较短的反应时间内重复使用多达五个循环，而产物收率没有任何重大损失，这是这种多相固体催化的独特特征。此外，更安全的反应曲线，高选择性，更高的收率，可靠的成本效益，简单的后处理条件是这种绿色环保工艺的一些值得注意的亮点。在计算机上对喹啉衍生物作为组
• Synthesis of calcium silicate nanoparticles and its catalytic application in Friedlander reaction
  作者：Jeyakannu Palaniraja、Prabhakarn Arunachalam、U. Vijayalakshmi、Mohamed A. Ghanem、Selvaraj Mohana Roopan

  DOI：10.1080/24701556.2016.1241274

  日期：2017.6.3

  This work describes the nitric acid catalysed synthesis of wollastonite (CaSiO3) nanoparticles (NP) from tetraethyl orthosilicate and calcium nitrate tetrahydrate. The formed calcium silicate nanoparticles were characterized by Fourier transform infrared spectroscopy (FTIR), Powder X-ray Diffraction (PXRD), and scanning electron microscopy (SEM) equipped with X-ray micro analysis. The CaSiO3 NPs showed

  这项工作描述了原硅酸四乙酯和硝酸钙四水合物的硝酸催化硅灰石（CaSiO 3）纳米颗粒（NP）的合成。形成的硅酸钙纳米粒子通过傅立叶变换红外光谱（FTIR），粉末X射线衍射（PXRD）和配备X射线显微分析的扫描电子显微镜（SEM）进行表征。CaSiO 3 NPs通过弗里德兰德反应合成喹啉显示出极好的收率（93％）。通过各种光谱技术对合成的化合物3-二甲基-7-硝基-9-苯基-3,4-二氢ac啶-1（2 H）-one进行了表征。
• Synthesis, characterization, and hypoglycemic efficacy of nitro and amino acridines and 4-phenylquinoline on starch hydrolyzing compounds: an in silico and in vitro study
  作者：Lohitha Narayanaswamy、Suresh Yarrappagaari、Srinivasulu Cheemanapallia、Rajeswara Reddy Saddala、V. Vijayakumar

  DOI：10.1007/s11224-020-01529-5

  日期：2020.10

  α-Glucosidase are important therapeutic targets for type II diabetes. The present focus of our study is to elucidate the hypoglycemic activity of novel compounds through in vitro and in silico studies. Here, we synthesized the nitro acridines ( 3a–3c), amino acridines (4a–4c ), and nitro phenylquinoline ( 3d) and amino phenylquinoline (4d ) using a multi-step reaction protocol in good yields. All the above derivatives

  α-淀粉酶和α-葡萄糖苷酶是II型糖尿病的重要治疗靶点。我们目前研究的重点是通过体外和计算机研究阐明新化合物的降血糖活性。在这里，我们使用多步反应方案以良好的收率合成了硝基吖啶 (3a-3c)、氨基吖啶 (4a-4c) 和硝基苯基喹啉 (3d) 和氨基苯基喹啉 (4d)。以阿卡波糖为标准药物，筛选所有上述衍生物的分子对接、α-淀粉酶和α-葡萄糖苷酶抑制活性。进行了计算机模拟研究以探索化合物与 α-淀粉酶和 α-葡萄糖苷酶活性位点的结合能力。3c 的体外抗高血糖报告显示出最大的抑制活性，IC 50 值为 200.61 ± 9.71 μmol/mL 和 197.76 ± 8。对 α-淀粉酶和 α-葡萄糖苷酶分别为 22 μmol/mL。类似地，化合物 3a 的 IC 50 值为 243.78 ± 13.25 μmol/mL 和 296.57 ± 10.66 μmol/mL，而 4c 的 IC 50
• Ultrasound promoted montmorillonite K-10 catalyzed synthesis, characterization, molecular modelling, SAR and hypoglycemic studies of new rhodanine bejeweled acridine analogues
  作者：Gangadhara Angajala、Valmiki Aruna、Pasupala Pavan、Pulikanti Guruprasad Reddy

  DOI：10.1016/j.molstruc.2021.130828

  日期：2021.10

  catalyst upto five cycles. In silico molecular docking studies were carried out to find out the effective binding affinity of the synthesized acridine analogues towards PPARγ protein (Id-2XKW). The results obtained showed that compounds 6c and 6g possess good binding interaction towards PPARγ with binding energy of -9.6 and -9.0 k.cal/mol which was greater than standard Acarbose (-8.9 k.cal/mol) and comparable

  在目前的工作中，一种有效的超声促进了 ( Z )-2-((4-chloro-2-(piperidin/morpholin-1-yl)thiazol-5-yl)methylene)-3,3,7,9 tetra甲基-3,4-二氢吖啶-1 (2 H ) -one 类似物6(ah)已经报道了使用 MK-10 催化剂通过 Knoevenagel 缩合。MK-10 由于其不同的性质和高表面积体积比，表现出对反应响应有利的特征，例如反应时间更短、后处理程序简单、反应过程干净，并且催化剂可重复使用多达五个循环，从而获得优异的产品收率. 进行了计算机分子对接研究，以找出合成的吖啶类似物对 PPARγ 蛋白 (Id-2XKW) 的有效结合亲和力。所得结果表明化合物6c和6g对 PPARγ 具有良好的结合相互作用，结合能为 -9.6 和 -9.0 k.cal/mol，高于标准阿卡波糖 (-8.9 k.cal/mol)，与标准吡格列酮
• Design, synthesis and evaluation of acridine and fused-quinoline derivatives as potential anti-tuberculosis agents
  作者：Gisela C. Muscia、Graciela Y. Buldain、Silvia E. Asís

  DOI：10.1016/j.ejmech.2013.12.013

  日期：2014.2

  The synthesis of twelve acridine and polycyclic acridine derivatives prepared via the Friedlander reaction is described. The one-pot reactions of 2-amino-5-chloro or 5-nitro-benzophenones and a variety of cydanones and indanones were carried out in a MW oven under TFA catalysis in good yields. The products were designed according natural antituberculosis products and were evaluated for growth inhibitory activity towards Mycobacterium tuberculosis H(37)Rv (Mtb) through the National Institute of Allergy and Infectious Diseases (NIAID, USA). Three of them underwent additional testings. The cyclopenta[b]quinoline derivative 9 and the acridine derivative 13 showed remarkable MIC values against the rifampin resistant strain. The former exhibited bactericidal activity at 50 mu g/mL, its intracellular activity is similar to rifampin and it was not cytotoxic at low concentrations so it can be considered a new lead compound. (C) 2013 Elsevier Masson SAS. All rights reserved.