6-methyl-2-(pyridin-4-yl)-1H-benzimidazole | 84123-77-3

• 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: 6-methyl-2-(pyridin-4-yl)-1H-benzimidazole
• 英文别名: 6-methyl-2-pyridin-4-yl-1H-benzimidazole
• CAS: 84123-77-3
• 化学式: C₁₃H₁₁N₃
• mdl: MFCD03779897
• 分子量: 209.25
• InChiKey: VSAHWCWASCZTME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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

反应信息

• 作为反应物：
  描述：

  6-methyl-2-(pyridin-4-yl)-1H-benzimidazole 在 硫酸 、 溴 、 硝酸 、 溶剂黄146 作用下， 反应 4.67h， 生成 6-bromo-5-methyl-4-nitro-2-pyridin-4-yl-1H-benzoimidazole
  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 6-methyl-2-(pyridin-4-yl)-1H-benzimidazole
  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

• A one-step synthesis of substituted benzo- and pyridine-fused 1H-imidazoles
  作者：Sonu Kumar、Manash P. Sarmah、Yella Reddy、Ashish Bhatt、Ravi Kant

  DOI：10.1080/00397911.2021.2001658

  日期：2022.1.2

  Abstract Substituted benzimidazoles and pyrimidazoles are an important group of heterocyclic aromatic organic compounds in the field of medicinal chemistry. A one-step microwave accelerated synthesis of substituted benzo- and pyridine-fused 1H-imidazoles has been described. Mechanistically, the reaction proceeds by reacting substituted 2-fluoronitrobenzene and substituted arylamine through the formation

  摘要 取代的苯并咪唑类和嘧唑类化合物是药物化学领域中一类重要的杂环芳香族有机化合物。已经描述了取代苯并和吡啶稠合的 1H-咪唑的一步微波加速合成。从机理上讲，该反应通过取代的 2-氟硝基苯和取代的芳基胺通过形成 N-羟基中间体进行反应，该中间体在较高温度下裂解得到所需的产物。与先前描述的合成方法相比，这种方法实现了反应时间的减少、更高的产率、更清洁的反应。
• 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。
• SUBSTITUTED HYDRAZIDE COMPOUNDS AND USE THEREOF
  申请人：Shi Xiulan

  公开号：US20120142921A1

  公开（公告）日：2012-06-07

  The invention relates to substituted hydrazide compounds as shown by general formula I, including geometrical isomers, pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, and use of the same, wherein the substitutents Ar and R have the same meanings as given in the Description. The invention further relates to the use of compounds of general formula I in the preparation of medicament for the treatment and/or prevention of cancer and other proliferative diseases.

  本发明涉及通式I所示的取代肼化合物，包括几何异构体、药学上可接受的盐、水合物、溶剂合物或前药，以及其使用，其中取代基Ar和R的含义与说明中给出的相同。本发明还涉及通式I化合物在制备用于治疗和/或预防癌症和其他增殖性疾病的药物中的使用。
• <i>N</i>,2,6-Trisubstituted 1<i>H</i>-benzimidazole derivatives as a new scaffold of antimicrobial and anticancer agents: design, synthesis, <i>in vitro</i> evaluation, and <i>in silico</i> studies
  作者：Em Canh Pham、Tuong Vi Le Thi、Huong Ha Ly Hong、Bich Ngoc Vo Thi、Long B. Vong、Thao Thanh Vu、Duy Duc Vo、Ngoc Vi Tran Nguyen、Khanh Nguyen Bao Le、Tuyen Ngoc Truong

  DOI：10.1039/d2ra06667j

  日期：——

  2-arylbenzimidazole derivatives followed by N-alkylation by conventional heating or microwave irradiation for diversification. Potent antibacterial compounds against MSSA and MRSA were discovered such as benzimidazole compounds 3k (2-(4-nitrophenyl), N-benzyl), 3l (2-(4-chlorophenyl), N-(4-chlorobenzyl)), 4c (2-(4-chlorophenyl), 6-methyl, N-benzyl), 4g (2-(4-nitrophenyl), 6-methyl, N-benzyl), and 4j (2-(4-nitrophenyl)

  含有苯并咪唑部分的化合物在发现新的生物活性物质方面占据着优越的化学空间。继续我们最近的工作，使用有效的合成方案（即焦亚硫酸钠催化芳香醛与邻苯二胺缩合形成 2-芳基苯并咪唑衍生物，然后形成N- ），设计并合成了 69 种苯并咪唑衍生物，收率高达 46-99%。通过常规加热或微波辐射进行烷基化以实现多样化。发现了针对 MSSA 和 MRSA 的有效抗菌化合物，例如苯并咪唑化合物3k (2-(4-硝基苯基), N-苄基), 3l (2-(4-氯苯基), N- (4-氯苄基)), 4c (2 -(4-氯苯基)，6-甲基， N-苄基)， 4g (2-(4-硝基苯基)，6-甲基， N-苄基)，和4j (2-(4-硝基苯基)，6-甲基， N- (4-氯苄基))，MIC 为 4–16 μg mL -1 。此外，化合物4c对大肠杆菌和粪链球菌表现出良好的抗菌活性（MIC = 16 μg mL -1 ）。此外，化合物3k
• SUBSTITUTED HYDRAZIDE COMPOUNDS AND APPLICATION THEREOF
  申请人：Shenyang J & Health Pharmaceutical Co., Ltd.

  公开号：EP2468730A1

  公开（公告）日：2012-06-27

  The invention relates to substituted hydrazide compounds as shown by general formula I, including geometrical isomers, pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, and use of the same, wherein the substitutents Ar and R having the same meanings as given in the Description. T The invention further relates to the use of compounds of general formula I in the preparation of medicament for the treatment and/or prevention of cancer and other proliferative diseases.

  本发明涉及通式I所示的取代酰肼化合物，包括几何异构体，其药学上可接受的盐、水合物、溶液或原药，以及其用途，其中取代基Ar和R的含义与说明书中给出的相同。T 本发明进一步涉及通式 I 化合物在制备治疗和/或预防癌症和其它增殖性疾病的药物中的用途。