(9ci)-2-乙基-5-硝基-1H-苯并咪唑 | 5805-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (9ci)-2-乙基-5-硝基-1H-苯并咪唑
• 英文名称: 2-ethyl-5-nitrobenzimidazole
• 英文别名: 5-nitro-2-ethyl-1H-benzo[d]imidazole；2-ethyl-5-nitro-1H-benzo[d]imidazole；2-ethyl-5-nitro-1H-benzimidazole；5-nitro-2-ethylbenzimidazole；2-ethyl-5-nitro-1(3)H-benzoimidazole；2-Aethyl-5-nitro-1(3)H-benzimidazol；2-ethyl-5(6)-nitro-benzimidazole；2-ethyl-6-nitro-1H-benzimidazole
• CAS: 5805-42-5
• 化学式: C₉H₉N₃O₂
• mdl: MFCD00457965
• 分子量: 191.189
• InChiKey: AAJAEEPAUQTYFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 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：

  (9ci)-2-乙基-5-硝基-1H-苯并咪唑 在 盐酸 、 碳酸氢钠 、 一水合肼 、 锌 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 2.59h， 生成 2-ethyl-5-(L-phenylalanyl)-amino 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 (9ci)-2-乙基-5-硝基-1H-苯并咪唑
  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

• Synthesis and Evaluation of Selected Benzimidazole Derivatives as Potential Antimicrobial Agents
  作者：Fatmah Alasmary、Anna Snelling、Mohammed Zain、Ahmed Alafeefy、Amani Awaad、Nazira Karodia

  DOI：10.3390/molecules200815206

  日期：——

  A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial activity of the compounds depended on the substituents attached to the bicyclic heterocycle. In particular, some compounds displayed

  合成了53个苯并咪唑衍生物的文库，它们在1、2和5位具有取代基，并针对一系列与医学相关的细菌和真菌参考菌株进行了筛选。SAR分析最有前景的结果表明，化合物的抗菌活性取决于与双环杂环相连的取代基。特别是，某些化合物对两种耐甲氧西林的金黄色葡萄球菌（MRSA）菌株表现出抗菌活性，其最低抑制浓度（MIC）与广泛使用的环丙沙星药物相当。这些化合物具有一些共同特征。三个具有5-卤素取代基；两个是（S）-2-乙胺苯并咪唑的衍生物；其他是一种2-（氯甲基）-1H-苯并[d]咪唑和（1H-苯并[d]咪唑-2-基）甲硫醇的衍生物。抗真菌筛选的结果也非常有趣：23种化合物对选定的真菌菌株显示出有效的杀真菌活性。它们的MIC值显示出比两性霉素B相同或更高的效力。5-卤代苯并咪唑衍生物被认为是有前途的广谱抗微生物候选物，值得进一步研究以用于潜在的治疗应用。
• 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。
• Novel silica tungstic acid (STA): Preparation, characterization and its first catalytic application in synthesis of new benzimidazoles
  作者：Bahador Karami、Vahideh Ghashghaee、Saeed Khodabakhshi

  DOI：10.1016/j.catcom.2012.01.012

  日期：2012.4

  A novel silica tungstic acid (STA) as a highly efficient catalyst has been synthesized and employed for the cyclocondensation of 1,2-phenylenediamines with orthoesters under solvent-free conditions. Catalyst loadings can be as low as 1 mol% to give high yields of the corresponding benzimidazoles at 80 °C. To make the catalyst, sodium tungstate reacted with silica chloride under refluxing n-hexane.

  合成了一种新型的二氧化硅钨酸（STA）作为高效催化剂，并用于无溶剂条件下1,2-苯二胺与原酸酯的环缩合反应。催化剂的负载量可低至1 mol％，以在80°C时获得高产率的相应苯并咪唑。为了使催化剂，钨酸钠与二氧化硅酰氯在回流下反应Ñ正己烷。通过X射线荧光，X射线衍射和傅立叶变换红外光谱对STA作为一种新型固体酸进行了表征。
• [EN] 5-SULFAMOYL-2-HYDROXYBENZAMIDE DERIVATIVES<br/>[FR] DÉRIVÉS DE 5-SULFAMOYL-2-HYDROXYBENZAMIDE
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2017153952A1

  公开（公告）日：2017-09-14

  The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R, R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及取代水杨酰胺衍生物。具体而言，本发明涉及根据公式(I)的化合物：其中R、R1和R2如本文所述，或其药用可接受的盐。本发明的化合物是CD73的抑制剂，可用于治疗癌症、前癌症综合症以及与CD73抑制相关的疾病，例如艾滋病、治疗HIV、自身免疫疾病、感染、动脉粥样硬化和缺血再灌注损伤。因此，本发明进一步涉及包含本发明化合物的药物组合物。本发明还进一步涉及使用本发明化合物或包含本发明化合物的药物组合物来抑制CD73活性和治疗与之相关的疾病的方法。
• Synthesis of 2-substituted benzimidazoles by iodine-mediated condensation of orthoesters with 1,2-phenylenediamines
  作者：Zhan-Hui Zhang、Jian-Jiong Li、Yuan-Zhe Gao、Yu-Heng Liu

  DOI：10.1002/jhet.5570440642

  日期：2007.11

  Iodine was found to be an efficient catalyst for the synthesis of 2-substituted benzimidazoles by the condensation of orthoesters and 1,2-phenylenediamines in good to excellent yields under mild reaction conditions.

  发现碘是在温和的反应条件下，通过原酸酯和1,2-苯二胺的缩合反应，可以高效合成2-取代的苯并咪唑的有效催化剂。

表征谱图