5-硝基-1-正丙基-1H-吲唑 | 1046454-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 5-硝基-1-正丙基-1H-吲唑
• 英文名称: 5-nitro-1-n-propyl-1H-indazole
• 英文别名: 1-propyl-5-nitro-1H-indazole；5-Nitro-1-propylindazole
• CAS: 1046454-17-4
• 化学式: C₁₀H₁₁N₃O₂
• 分子量: 205.216
• InChiKey: SMOXXFYECBIRKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-硝基-1-正丙基-1H-吲唑 在 palladium on activated charcoal 肼 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以90%的产率得到5-amino-1-n-propyl-1H-indazole
  参考文献：
  名称：

  An expedient, regioselective synthesis of novel 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]- and -[4,5-g]indazoles and their anticancer potential

  摘要：

  Several novel 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]- and -[4,5-g]indazoles and their 6-alkyl and 8-alkyl derivatives have been synthesised in high overall yields starting from 5-nitro and 6-nitro-indazoles in a three-step route involving the regioselective cyclisation of thioureidoindazoles and indazolyl dithiocarbamates as the key steps. Some assorted thiazoloindazoles have been screened for anticancer properties, which demonstrated the anticancer potential of at least one product, justifying its further follow-up. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.009
• 作为产物：
  描述：

  5-硝基吲唑 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-硝基-1-正丙基-1H-吲唑
  参考文献：
  名称：

  3H-呋喃[2,3-b]咪唑并[4,5-f]喹啉和3H-呋喃[2,3-b]吡唑并[4,3-f]喹啉作为新型抗菌剂的合成

  摘要：

  随着当前的挑战，由于抗生素耐药性细菌的增长，寻找新的抗生素化合物的需求也在增加。本研究获得了一些新的3 H-呋喃[2,3- b ]咪唑并[4,5- f ]喹啉和3 H-呋喃-[2,3- b ]吡唑并[4,3- f ]喹啉1-烷基-5-硝基-1 H-苯并咪唑和1-烷基-5-硝基-1 H-吲唑与2-(5-甲基呋喃-2-基)乙腈以高产率反应。新化合物的结构通过光谱(FT-IR, 1 H NMR, 13C NMR）和分析数据。抗菌筛选表明，标题化合物对革兰氏阳性菌和革兰氏阴性菌均非常有效，其 MIC 值与氨苄青霉素、青霉素 G 和磺胺甲恶唑等知名抗菌剂相当。结果表明，咪唑核心是抗菌试验中的药效团。

  DOI：

  10.1007/s11094-022-02622-1

文献信息

• Design, Synthesis, Fluorescence Properties and Antibacterial Activities of New 8-Chloro-3-Alkyl-3H-Pyrazolo[4,3-a]acridine-11-Carbonitriles
  作者：Zeynab Rahmani、Mehdi Pordel、Abolghasem Davoodnia

  DOI：10.5012/bkcs.2014.35.2.551

  日期：2014.2.20

  The treatment of alkylated nitro derivatives of indazole with 2-(4-chlorophenyl)acetonitrile under basic conditions gave the new 8-chloro-3-alkyl-3H-pyrazolo[4,3-a]acridine-11-carbonitriles via the nucleophilic substitution of hydrogen which proceeds at room temperature with concomitant cyclisation in fairly good yields. The structures of all newly synthesized compounds were confirmed by IR, $^1H$ NMR, $^13}C$ NMR and mass spectral data. Fluorescence experimental results of all newly synthesized compounds revealed remarkable photoluminescence properties and strong green fluorescence properties. Also, the new compounds exhibited potent antibacterial activity and their antibacterial activity (MIC) against Gram positive (Staphylococcuse aureus methicillin resistant S. aureus and Bacillus subtilis) and negative bacterial (Pseudomonas aeruginosa and Escherichia coli) species were determined.

  在碱性条件下，用 2-(4-氯苯基)乙腈处理吲唑的烷基化硝基衍生物，通过氢的亲核取代，在室温下进行同时环化，得到了新的 8-氯-3-烷基-3H-吡唑并[4,3-a]吖啶-11-腈，产率相当高。红外光谱、$^1H$核磁共振、$^13}C$核磁共振和质谱数据证实了所有新合成化合物的结构。所有新合成化合物的荧光实验结果均显示出显著的光致发光特性和强烈的绿色荧光特性。此外，新化合物还表现出了很强的抗菌活性，并测定了它们对革兰氏阳性菌（金黄色葡萄球菌、耐甲氧西林金黄色葡萄球菌和枯草杆菌）和阴性菌（绿脓杆菌和大肠杆菌）的抗菌活性（MIC）。
• Synthesis, characterisation, optical properties and theoretical calculations of a new fluorescent heterocyclic system: 3<i>H</i>-benzo[<i>a</i>]pyrazolo[3,4-<i>j</i>]acridine
  作者：Hamideh Alipoor、Mehdi Pordel、Ali Morsali

  DOI：10.3184/174751917x14967701766914

  日期：2017.7

  Four new fluorescent dyes derived from the 3H-benzo[a]pyrazolo[3,4-j]acridine system were synthesised and fully characterised by 1H NMR, 13C NMR, mass and analytical data. These new fluorophores were prepared from the reaction of 1-alkyl-5-nitro-1H-indazoles with 1-naphthylacetonitrile via nucleophilic substitution of hydrogen, in high yields. The optical properties of the dyes were also investigated

  合成了四种源自 3H-苯并[a] 吡唑并 [3,4-j] 吖啶系统的新型荧光染料，并通过 1H NMR、13C NMR、质量和分析数据进行了充分表征。这些新的荧光团是由 1-烷基-5-硝基-1H-吲唑与 1-萘基乙腈通过氢的亲核取代反应制备的，产率很高。还研究了染料的光学特性，结果表明，在某些情况下，与众所周知的荧光染料（如荧光素）相比，它们具有更高的量子产率。溶剂对四种化合物荧光特性的影响表明，发射波长随着溶剂极性的增加而红移。此外，密度泛函理论计算使用 B3LYP 混合泛函和 6-311++G(d, p) 基组提供了化合物的优化几何形状和相关前沿轨道。还使用时间相关密度泛函理论方法获得了计算的电子吸收光谱。
• Synthesis of New Fluorescent Pyrazolo[4,3-<i>a</i>]Acridine Derivatives Having Strong Antibacterial Activities
  作者：Leila Rezaei Daghigh、Mehdi Pordel、Abolghasem Davoodnia

  DOI：10.3184/174751914x13932618023986

  日期：2014.4

  New 3 H-pyrazolo[4,3- a]acridine derivatives have been prepared by the reaction of 1-alkyl-5-nitro-1 H-indazole with phenylacetonitrile and 2-(4-bromophenyl)acetonitrile in basic conditions via the nucleophilic substitution of hydrogen and concomitant cyclisation. The new compounds exhibited potent antibacterial activities and their antibacterial activities against Gram positive ( Staphylococcus aureus, methicillin resistant S. aureus and Bacillus subtilis) and Gram negative bacterial ( Pseudomonas aeruginosa and Escherichia coli) species were determined. The fluorescence properties of these derivatives were also studied.

  1- 烷基-5-硝基-1 H-吲唑与苯乙腈和 2-(4-溴苯基)乙腈在碱性条件下通过氢的亲核取代和伴随的环化反应，制备了新的 3 H-吡唑并[4,3-a]吖啶衍生物。这些新化合物具有很强的抗菌活性，并测定了它们对革兰氏阳性菌（金黄色葡萄球菌、耐甲氧西林金黄色葡萄球菌和枯草杆菌）和革兰氏阴性菌（绿脓杆菌和大肠杆菌）的抗菌活性。还研究了这些衍生物的荧光特性。
• Imidazo[4,5-a]acridines and Pyrazolo[4,3-a]acridines as a New Class of Urease Inhibitors: Synthesis, In Vitro Interactions, and Molecular Docking Studies
  作者：Javad Mohammadi、Mehdi Pordel、Mohammad Reza Bozorgmehr

  DOI：10.1007/s11094-024-03097-y

  日期：2024.3

  Despite the important role that urease plays in the global nitrogen cycle, inhibition of its activity is demanded owing to the development of diseases such as stomach ulcers and some cancers. In the search for a potent urease inhibitor, imidazoacridine and pyrazoloacridine derivatives were synthesized and evaluated for their urease inhibitory potential. The desired compounds were obtained in two steps

  尽管脲酶在全球氮循环中发挥着重要作用，但由于胃溃疡和某些癌症等疾病的发生，需要抑制其活性。在寻找有效的脲酶抑制剂的过程中，合成了咪唑吖啶和吡唑吖啶衍生物并评估了它们的脲酶抑制潜力。在碱性介质中分两步以高产率获得所需化合物。与标准硫脲相比，标题化合物表现出不同程度的抑制相互作用潜力，IC 50值在14.83±0.03和22.21±0.6μM之间。为了了解大多数活性类似物与脲酶活性位点的结合相互作用，还进行了复合物（配体-酶）的分子建模。
• Synthesis, Antiviral, Antibacterial, and Cytotoxicity Assessment of Some 3H-Benzo[a]imidazo[4,5-j]acridines and 3H-Benzo[a]pyrazolo[3,4-j]acridines
  作者：M. Faramarzi、M. Pordel、A. Morsali

  DOI：10.1134/s1070428020080151

  日期：2020.8

  Some novel 3H-benzo[a]imidazo[4,5-j]acridines and 3H-benzo[a]pyrazolo[3,4-j]acridines were synthesized by the reaction of 1-alkyl-5-nitro-1H-benzoimidazoles and 1-alkyl-5-nitro-1H-indazoles with 1-naphthylacetonitrile in high yields. The structures of the new compounds were determined by spectral (FTIR,H-1, and(13)C NMR) and analytical data. The antiviral activity of the synthesized compounds was tested against a panel of DNA and RNA viruses, including herpes simplex virus-1 KOS, vesicular stomatitis virus, herpes simplex virus-2 (G), vaccinia virus, and herpes simplex virus-1 TK-KOS ACVr. Most of the test compounds showed moderate activities in comparison with their corresponding reference standards. The synthesized compounds were also tested for antibacterial activity against a panel of strains of gram-negative and gram-positive bacterial species, and some of them we found as effective against gram- positive bacteria as well-known antibacterial agents, such as Cephalexin. The products we found to be cytostatic in the higher micromolar range.