2-propyl-5-nitro-1H-benzo[d]imidazole | 5805-43-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-propyl-5-nitro-1H-benzo[d]imidazole
• 英文别名: 2-propyl-5-nitrobenzoimidazole；6-nitro-2-propyl-1H-benzimidazole
• CAS: 5805-43-6
• 化学式: C₁₀H₁₁N₃O₂
• mdl: MFCD00447625
• 分子量: 205.216
• InChiKey: YPWVUEVXSQTBCL-UHFFFAOYSA-N

物化性质

• 熔点：
  159-161 °C
• 沸点：
  441.6±18.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-propyl-5-nitro-1H-benzo[d]imidazole 在 盐酸 、 锌 作用下， 以 水 为溶剂， 反应 1.0h， 以72%的产率得到5-amino-2-propyl benzimidazole
  参考文献：
  名称：

  New Antibacterial Peptide Analogs of 5-Aminobenzimidazoles

  摘要：

  새로운펩티드 유사체인 5a-c를 5-氨基苯并咪唑 2a-c과 L-phenylalanine과의 커플링반응에 의해 합성하였다.Phenylalanine의 amine 부을 phthalic anhydride 보호하고, 나머지 작용기인 carboxylic acid 를 염소화시켜서 hthaloyl-Lphenylalanyl chloride 4를 합성한 다음에, 화합물 2a-c와 반응시켜서 화합물 5a-c를 합성하였다.얻어진 화합물 5a-c를 hydrazine으로 반응시켜서 새로운 펩티드 유사체인 6a-c를 합성하였으며, 얻어진 화합물에 대한 항균성을 측정하였다. 通过将 5-氨基苯并咪唑 2a-c 与 L-苯丙氨酸偶联，获得了三种新的肽类似物 5a-c。为此，用邻苯二甲酸酐封堵了${\alpha}$-氨基，并通过制备邻苯二甲酰-L-苯丙氨酸氯4激活了${\alpha}$-苯丙氨酸的羧基。肽键连接成功后，用肼水合物处理 5a-c 除去邻苯二甲酰基团，得到游离肽 6a-c，并通过 Amberlite（IR-4B）柱纯化。根据红外光谱、1H NMR 和 EIMS 分析，对所有这些化合物 2a-c 和 5、6a-c 进行了表征。此外，还报告了这些化合物的抗菌活性。

  DOI：

  10.5012/jkcs.2011.55.4.650
• 作为产物：
  描述：

  4-硝基邻苯二胺 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 2-propyl-5-nitro-1H-benzo[d]imidazole
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new 5-nitro benzimidazole derivatives as AT1 antagonists with anti-hypertension activities

  摘要：

  The design, synthesis, in vitro and in vivo evaluation of 5-nitro benzimidazole with 1,4-disubsituted or 1,5-disubsituted indole derivatives as novel angiotensin II receptor antagonist is outlined. Radioligand binding assays showed that 2-(4-((2-butyl-5-nitro-1H-benzo[d] imidazol-1-yl) methyl)-1H-indol-1-yl) benzoic acid, compound 3, displayed a high affinity for the angiotensin II type 1 receptor with IC50 value of 1.03 +/- 0.26 nM. The biological evaluation on spontaneously hypertensive rats and renal hypertensive rats showed that 3 could cause significant decrease on MBP in a dose dependent manner, whose maximal response lowered 30 mmHg of MBP at 5 mg/kg and 41 mmHg of MBP at 10 mg/kg after oral administration, and the significant antihypertensive effect lasted beyond 24 h, which is better than Losartan. Taken together 3 could be considered as an effective and durable anti-hypertension drug candidate. These encouraging results are deserved of further investigation towards its use for therapeutic benefit. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.008

文献信息

• Ag–TiO₂/Clay Composite Photocatalyst for the Oxidation–Cyclization of 1,2-Diamine Compounds with Propylene Glycol or Alcohols
  作者：Kaliyamoorthy Selvam、Mari Annadhasan、Rengasamy Velmurugan、Meenakshisundaram Swaminathan

  DOI：10.1246/bcsj.20090319

  日期：2010.7.15

  Silver-loaded TiO2 (Ag–TiO2) and acidic clay (K10 montmorillonite) composite photocatalyst has been successfully applied for the light-induced conversion of o-phenylenediamine (OPD) and its derivatives to substituted benzimidazoles with various alcohols in acetonitrile using UV-A and solar light. The influence of the various photocatalysts, solvents, and substituents on the yield and selectivity of the products has been investigated. The mechanism of photocatalysis is proposed. Loading silver on TiO2 enhances product yield and selectivity both in UV and solar light. In the presence of primary alcohols, 2-aminothiophenol forms only disulfide and hence Ag–TiO2/clay can be used as a green catalyst for the synthesis of disulfides.

  负载银的TiO2（Ag–TiO2）和酸性粘土（K10蒙脱石）复合光催化剂已成功应用于紫外A和太阳光诱导的邻苯二胺（OPD）及其衍生物与多种醇在乙腈中的光催化转化合成取代苯并咪唑。考察了不同光催化剂、溶剂和取代基对产物收率和选择性的影响。提出了光催化机理。在TiO2上负载银可以提高紫外和太阳光下产物的收率和选择性。在存在一级醇的情况下，2-氨基硫酚仅形成二硫化物，因此Ag–TiO2/粘土可用作合成二硫化物的绿色催化剂。
• Copper-Catalyzed Synthesis of Benzimidazoles via Cascade Reactions of <i>o</i>-Haloacetanilide Derivatives with Amidine Hydrochlorides
  作者：Daoshan Yang、Hua Fu、Liming Hu、Yuyang Jiang、Yufen Zhao

  DOI：10.1021/jo8014984

  日期：2008.10.3

  developed an efficient method for the synthesis of benzimidazoles via cascade reactions of o-haloacetoanilide derivatives with amidine hydrochlorides. The protocol uses 10 mol % CuBr as the catalyst, Cs2CO3 as the base, and DMSO as the solvent, and no ligand is required. The procedure proceeds via the sequential coupling of o-haloacetoanilide derivatives with amidines, hydrolysis of the intermediates (amides)

  我们已经开发了一种通过邻卤代乙酰苯胺衍生物与with盐酸盐的级联反应合成苯并咪唑的有效方法。该方案使用10 mol％的CuBr作为催化剂，使用Cs2CO3作为碱，使用DMSO作为溶剂，并且不需要配体。该过程通过邻卤代乙酰苯胺衍生物与am的顺序偶联，中间体（酰胺）的水解以及分子内环化（损失NH3）进行，得到2取代的1H-苯并咪唑。
• Baker’s Yeast-Mediated Regioselective Reduction of 2,4-Dinitroacylanilines: Synthesis of 2-Substituted 6-Nitrobenzimidazoles
  作者：Arturo Navarro-Ocaña、Luís F. Olguín、Manuel Jiménez-Estrada、Eduardo Bárzana

  DOI：10.1055/s-2004-837203

  日期：——

  Several 2,4-dinitro-N-acylanilines were regioselectively reduced at the C-2 position by baker's yeast in slightly basic media (pH = 7.5) to afford 2-amino-4-nitroacylanilines, which were then cyclized under acidic conditions to the corresponding 2-substituted-6-nitrobenzimidazoles. The benzimidazoles thus obtained can be employed as precursors for bioactive derivatives.

  几种 2,4-二硝基-N-酰基苯胺在微碱性介质（pH = 7.5）中被面包酵母在 C-2 位置区域选择性还原，得到 2-氨基-4-硝基酰基苯胺，然后在酸性条件下环化为相应的 2-取代-6-硝基苯并咪唑。由此获得的苯并咪唑可用作生物活性衍生物的前体。
• Oxone-mediated annulation of 2-aminobenzamides and 1,2-diaminobenzenes with<i>sec</i>-amines<i>via</i>imine-<i>N</i>-oxides: new syntheses of 2,3-dihydroquinazolin-4(1<i>H</i>)-ones and 1<i>H</i>-benzimidazoles
  作者：Vinodkumar Sriramoju、Srinivas Kurva、Sridhar Madabhushi

  DOI：10.1039/c7nj04939k

  日期：——

  An efficient and mild method for the preparation of 2,3-dihydroquinazolin-4(1H)-ones and 1H-benzimidazoles by the oxone-mediated reaction of sec-amines via imine-N-oxides with 2-amino-N-substituted benzamides and 1,2-diaminobenzenes respectively in THF–water (2 : 1) at ambient temperature is described.

  2,3-二氢喹唑啉4的制备一种有效的和温和的方法（1 ħ） -酮和1- ħ通过的过硫酸氢钾介导的反应-benzimidazoles秒-胺通过亚胺Ñ -oxides与2-氨基- ñ -描述了室温下分别在THF-水（2：1）中的取代的苯甲酰胺和1,2-二氨基苯。
• Synthesis of methanesulphonamido-benzimidazole derivatives as gastro-sparing antiinflammatory agents with antioxidant effect
  作者：Ratika Sharma、Alka Bali、Bhim Bahadur Chaudhari

  DOI：10.1016/j.bmcl.2017.05.017

  日期：2017.7

  A series of 5-methanesulphonamido benzimidazole derivatives were designed by combining the structural features of clinically useful anti-inflammatory drugs (nimesulide and rofecoxib) and antiulcer drugs (lansoprazole, omeprazole, etc.) based on physicochemical and 3D similarity studies. The compounds were evaluated for their anti-inflammatory activity in carrageenan induced rat paw edema model taking

  根据理化和3D相似性研究，结合临床上有用的消炎药（尼美舒利和罗非考昔）和抗溃疡药（兰索拉唑，奥美拉唑等）的结构特征，设计了一系列5-甲磺酰胺基苯并咪唑衍生物。以罗非考昔和消炎痛为标准药物，在角叉菜胶诱导的大鼠爪水肿模型中评估了这些化合物的抗炎活性。通过铁氰化钾还原能力（PFRAP）测定法评估化合物的体外抗氧化活性。化合物9，10和11显示出抗炎活性相媲美的标准组并且也是在测试剂量非致溃疡。化合物6– 11在浓度范围（1.0–50.0 µmol / ml）中表现出良好的抗氧化作用。根据所选理化性质的计算，化合物的初步理论ADME分析显示出极好的Lipinski规则。