1-isobutyl-5-nitro-1H-indazole | 1609131-09-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 1-isobutyl-5-nitro-1H-indazole
• 英文别名: 1-(2-methylpropyl)-5-nitroindazole
• CAS: 1609131-09-0
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: ZAEIWQJPOLQIAO-UHFFFAOYSA-N

物化性质

• 沸点：
  355.2±15.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1-isobutyl-5-nitro-1H-indazole 在 水 、 铁粉 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 4.33h， 以332 mg的产率得到1-isobutyl-1H-indazol-5-amine
  参考文献：
  名称：

  NOVEL AMINE DERIVATIVE OR SALT THEREOF AS TNF ALPHA INHIBITORS

  摘要：

  公开号：

  EP2915804B1
• 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 1-isobutyl-5-nitro-1H-indazole
  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 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。
• NOVEL AMINE DERIVATIVE OR SALT THEREOF
  申请人：TOYAMA CHEMICAL CO., LTD.

  公开号：US20150299189A1

  公开（公告）日：2015-10-22

  A novel amine derivative expressed by general formula (1) (in the formula: G 1 , G 2 , and G 3 are the same or different and represent CH or a nitrogen atom; R 1 represents a chlorine atom, an optionally-substituted C 3-8 cycloalkyl group, or the like; R 2 represents —COOR 5 (in the formula, R 5 represents a hydrogen atom or a carboxyl protective group), or the like; R 3 represents a hydrogen atom, or the like; and R 4 represents an optionally-substituted condensed bicyclic hydrocarbon group, an optionally-substituted bicyclic heterocyclic group, or the like), or a salt thereof is useful in procedures such as the treatment or prevention of conditions related to excessive keratinocyte proliferation.

  一种新的胺衍生物，其通式为（1）（其中：G1、G2和G3相同或不同，代表CH或氮原子；R1代表氯原子、可选取代的C3-8环烷基团等；R2代表—COOR5（在公式中，R5代表氢原子或羧保护基）等；R3代表氢原子等；R4代表可选取代的紧缩双环碳氢基团、可选取代的双环杂环基团等），或其盐，在治疗或预防与过度角质细胞增殖有关的疾病过程中非常有用。
• WO2020010252A5
  申请人：——

  公开号：WO2020010252A5

  公开（公告）日：2022-07-05
• 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.