5-methyl-2-(pyridin-3-yl)-1H-benzo[d]imidazole | 84123-76-2

• 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: 5-methyl-2-(pyridin-3-yl)-1H-benzo[d]imidazole
• 英文别名: 6-methyl-2-pyridin-3-yl-1H-benzimidazole
• CAS: 84123-76-2
• 化学式: C₁₃H₁₁N₃
• mdl: MFCD01250225
• 分子量: 209.25
• InChiKey: WVYGCHDGGVPIBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-methyl-2-(pyridin-3-yl)-1H-benzo[d]imidazole 在 palladium on activated charcoal 硫酸 、 氢气 、 溴 、 硝酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 110.0 ℃ 、344.74 kPa 条件下， 反应 12.67h， 生成 5-Methyl-2-pyridin-3-yl-1H-benzoimidazol-4-ylamine
  参考文献：
  名称：

  Differential antiproliferative activity of new benzimidazole-4,7-diones

  摘要：

  Ten benzimidazole-4,7-diones were synthesized and tested in vitro on two tumor cell lines. Several compounds showed a significant antiproliferative activity on K562 cells, although to a different extent, whereas compound 1i showed a highly significant activity on SW620 cells, comparable to that of doxorubicin. Both the substituents in the quinone ring and the position of the nitrogen atom in the pyridine moiety play a crucial role for the biological activity.

  DOI：

  10.1016/j.farmac.2004.04.001
• 作为产物：
  描述：

  4-甲基-2-硝基苯胺 在 tin(ll) chloride 作用下， 以 甲醇 、 硝基苯 为溶剂， 反应 5.0h， 生成 5-methyl-2-(pyridin-3-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Differential antiproliferative activity of new benzimidazole-4,7-diones

  摘要：

  Ten benzimidazole-4,7-diones were synthesized and tested in vitro on two tumor cell lines. Several compounds showed a significant antiproliferative activity on K562 cells, although to a different extent, whereas compound 1i showed a highly significant activity on SW620 cells, comparable to that of doxorubicin. Both the substituents in the quinone ring and the position of the nitrogen atom in the pyridine moiety play a crucial role for the biological activity.

  DOI：

  10.1016/j.farmac.2004.04.001

文献信息

• Microwave-Assisted Nickel-Catalyzed Synthesis of Benzimidazoles: Ammonia as a Cheap and Nontoxic Nitrogen Source
  作者：Fang Ke、Peng Zhang、Yiwen Xu、Xiaoyan Lin、Jin Lin、Chen Lin、Jianhua Xu

  DOI：10.1055/s-0037-1610843

  日期：2018.12

  efficient and convenient Ni-catalyzed C–N bond formation for the synthesis of various benzimidazoles from various 2-haloanilines, aldehydes, and ammonia in a concise manner is reported. This protocol uses commercially available, nonhazardous, clean ammonia as a reaction partner instead of other nitrogen sources. Benzimidazoles, as the sole products, were obtained in high to excellent yields (up to 95%)

  报道了一种高效且方便的 Ni 催化 C-N 键形成，用于以简洁的方式从各种 2-卤代苯胺、醛和氨合成各种苯并咪唑。该协议使用市售的、无害的、清洁的氨作为反应伙伴，而不是其他氮源。苯并咪唑作为唯一的产品，以高到极好的收率（高达 95%）获得。
• Synthesis of benzimidazoles by CuI-catalyzed three-component reaction of 2-haloaniline, ammonia and aldehyde in water
  作者：Fang Ke、Peng Zhang、Chen Lin、Xiaoyan Lin、Jianhua Xu、Xiangge Zhou

  DOI：10.1039/c8ob02172d

  日期：——

  An efficient copper-catalyzed three-component reaction of 2-haloaniline, ammonia and aldehyde for the synthesis of benzimidazoles with 1,10-phenanthroline as the ligand has been developed. A variety of substituted benzimidazole derivatives can be obtained in yields up to 95%.

  开发了一种高效的铜催化的2-卤代苯胺，氨和醛的三组分反应，以1,10-菲咯啉为配体合成苯并咪唑。可以以高达95％的产率获得各种取代的苯并咪唑衍生物。
• Synthesis of benzoxazoles, benzothiazoles and benzimidazoles and evaluation of their antifungal, insecticidal and herbicidal activities.
  作者：TAKUZO HISANO、MASATAKA ICHIKAWA、KONOSUKE TSUMOTO、MASANOBU TASAKI

  DOI：10.1248/cpb.30.2996

  日期：——

  Benzoxazoles, benzothiazoles and benzimidazoles having substituents on the azole and benzene nuclei were synthesized evaluated for antifungal, insecticidal and herbicidal activities. It was found that benzimidazoles tended to exhibit antifungal activity while benzothiazoles tended to show herbicidal activity. Chloro, trifluoromethyl, methoxy and ethoxy groups at the 5 position were potent substituents, and the 2-pyridyl group at the 2 position is a common structural unit. Among several active derivatives, 7-chloro-2-(2-pyridyl) benzimidazole and 2-(2-pyridyl)-5-trifluoromethylbenzothiazole exhibited significant activity against Panonycus citri.

  合成了在偶氮和苯环上具有取代基的苯并噁唑、苯并噻唑和苯并咪唑，并评估其抗真菌、杀虫和除草活性。研究发现，苯并咪唑倾向于表现出抗真菌活性，而苯并噻唑则倾向于显示除草活性。在5位位置上的氯、三氟甲基、甲氧基和乙氧基基团是有效的取代基，而在2位位置的吡啶基是一个常见的结构单元。在几种具有活性的衍生物中，7-氯-2-(2-吡啶基)苯并咪唑和2-(2-吡啶基)-5-三氟甲基苯并噻唑对柑橘红蜘蛛表现出显著活性。
• Dihydrothienopyrimidines for the Treatment of Inflammatory Diseases
  申请人：Pouzet Pascale

  公开号：US20080096882A1

  公开（公告）日：2008-04-24

  The invention relates to new dihydrothienopyrimidine of formula 1, as well as pharmacologically acceptable salts, diastereomers, enantiomers, racemates, hydrates or solvates thereof, wherein X is SO or SO 2 , but preferably SO, and wherein R 1 , R 2 and R 3 have the meanings given in the description, and which are suitable for the treatment of respiratory or gastrointestinal complaints or diseases, inflammatory diseases of the joints, skin or eyes, diseases of the peripheral or central nervous system or cancers, as well as pharmaceutical compositions which contain these compounds.

  该发明涉及公式1的新二氢噻吡嘧啶，以及其药理学上可接受的盐、对映体、旋光异构体、消旋体、水合物或溶剂合物，其中X为SO或SO2，但最好为SO，R1、R2和R3在描述中给出的含义，并且适用于治疗呼吸道或胃肠道疾病、关节、皮肤或眼睛的炎症性疾病、外周或中枢神经系统疾病或癌症，以及含有这些化合物的药物组合物。
• Design, Microwave‐Assisted Synthesis and in Vitro Antibacterial and Antifungal Activity of 2,5‐Disubstituted Benzimidazole
  作者：Yanpeng Shi、Kai Jiang、Ran Zheng、Jiaxu Fu、Liuqing Yan、Qiang Gu、Yumin Zhang、Feng Lin

  DOI：10.1002/cbdv.201800510

  日期：2019.3

  5‐disubstituted benzimidazole derivatives were designed, synthesized and evaluated for their antibacterial activities. The tested compounds B1–B4 and C2–C6 exhibited not only good antifungal activity but also favorable broad‐spectrum antibacterial activity. Also, the lowest MIC of antibacterial and antifungal activity was 2 μg/mL and 4 μg/mL, respectively. It suggested that the structure of compound including the

  设计、合成了 17 种新型 2,5-二取代苯并咪唑衍生物并评估了它们的抗菌活性。受试化合物B1-B4和C2-C6不仅表现出良好的抗真菌活性，而且具有良好的广谱抗菌活性。此外，抗菌和抗真菌活性的最低 MIC 分别为 2 μg/mL 和 4 μg/mL。这表明包括不同取代基及其位点的化合物的结构直接影响合成化合物的功效。