7-methyl-2-(pyridin-2-yl)-1H-benzo[d]imidazole | 68118-45-6

• 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: 7-methyl-2-(pyridin-2-yl)-1H-benzo[d]imidazole
• 英文别名: 7-Methyl-2-(2-pyridyl)benzimidazol；4-methyl-2-pyridin-2-yl-1(3)H-benzoimidazole；4-methyl-2-pyridin-2-yl-1H-benzimidazole
• CAS: 68118-45-6
• 化学式: C₁₃H₁₁N₃
• mdl: MFCD20390375
• 分子量: 209.25
• InChiKey: IHHKHEKVCAJPKE-UHFFFAOYSA-N

物化性质

• 熔点：
  144.0-144.5 °C(Solv: hexane (110-54-3); acetone (67-64-1))
• 沸点：
  438.0±37.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

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：

  4-乙烯基吡啶 、 7-methyl-2-(pyridin-2-yl)-1H-benzo[d]imidazole 在 溶剂黄146 作用下， 以38.2%的产率得到7-Methyl-2-pyridin-2-yl-1-(2-pyridin-4-yl-ethyl)-1H-benzoimidazole
  参考文献：
  名称：

  Ichikawa, Masataka; Yamamoto, Chiyuki; Hisano, Takuzo, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 10, p. 3042 - 3047

  摘要：

  DOI：
• 作为产物：
  描述：

  7-Methyl-2-pyridin-2-yl-1-(2-pyridin-4-yl-ethyl)-1H-benzoimidazole 在 三氯化铝 作用下， 以 various solvent(s) 为溶剂， 反应 0.5h， 生成 7-methyl-2-(pyridin-2-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Ichikawa, Masataka; Yamamoto, Chiyuki; Hisano, Takuzo, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 10, p. 3042 - 3047

  摘要：

  DOI：

文献信息

• Synthesis and Biological Evaluation of Novel Benzimidazole Derivatives and Analogs Targeting the NLRP3 Inflammasome
  作者：Liangkun Pan、Nan Hang、Chao Zhang、Yu Chen、Shuchun Li、Yang Sun、Zhongjun Li、Xiangbao Meng

  DOI：10.3390/molecules22020213

  日期：——

  synthesized and their antiinflammatory activities toward NLRP3 (nucleotide-binding domain leucine-rich repeat containing protein family，pyrin domain-containing 3，also known as cryopyrin or NALP3) inflammasome were evaluated in vitro. Two lead compounds, TBZ-09 and TBZ-21, were identified by antiproduction of IL-1β. In the second round of biological evaluation, based on the lead, 34 more compounds were synthesized

  合成了一系列噻唑的苯并[d]咪唑类似物，并评估了它们对炎性体NLRP3（核苷酸结合结构域富含亮氨酸的重复序列，含有蛋白质家族，含有pyrin结构域的家族3，也称为冻菌素或NALP3）的抗炎活性。 。通过产生IL-1β鉴定了两种先导化合物TBZ-09和TBZ-21。在第二轮生物学评估中，以铅为基础，又合成了34种化合物，并研究了它们的体外抗炎活性。几种化合物被鉴定为可以以剂量依赖的方式降低IL-1β表达的抗炎药。初步的构效关系也总结在这里。
• Amberlite IR-120(H)-mediated “on water” synthesis of novel anticancer ruthenium(<scp>ii</scp>)–p-cymene 2-pyridinylbenzothiazole (BTZ), 2-pyridinylbenzoxazole (BOZ) &amp; 2-pyridinylbenzimidazole (BIZ) scaffolds
  作者：Sunisha Kottukulam Subran、Swagata Banerjee、Ashaparna Mondal、Priyankar Paira

  DOI：10.1039/c6nj02049f

  日期：——

  novel, green and effective methodology for the synthesis of Ru(II)–arene 2-pyridinylbenzothiazole, Ru(II)–arene 2-pyridinylbenzoxazole & Ru(II)–arene 2-pyridinylbenzimidazole complexes in a one-pot sequence. A convenient and clean “on water” synthesis of organoruthenium is reported. Amberlite IR-120(H) has been employed as a reusable catalyst in this reaction. The operational simplicity, excellent yield

  在这里，我们介绍了一种新颖，绿色，有效的合成Ru（II）-芳烃基2-吡啶基苯并噻唑，Ru（II）-芳烃基2-吡啶基苯并恶唑和Ru（II）的方法。）-一键序列中的芳烃2-吡啶基苯并咪唑配合物。据报道，一种方便，清洁的“水上”有机钌合成方法。在该反应中，已使用Amberlite IR-120（H）作为可重复使用的催化剂。该方法的主要优点是操作简便，产率高，产物分离容易和化学选择性高。此外，该过程是经济，安全和环境友好的。这种方法提供了合成多种新型有机钌支架以进行抗癌筛选的机会。与顺铂相比，此处呈现的大多数化合物对MCF7，Hela和A2780细胞系均表现出显着的细胞毒性和选择性。因为，[（η 6 - p -cymene）的Ru-2-（6-溴吡啶-2-基） -苯并[ d就癌细胞系的细胞毒性和选择性而言，] [噻唑]（4g）被确定为最有效的荧光支架，可用于癌症治疗学。
• 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。
• INHIBITORS OF INV(16) LEUKEMIA
  申请人：The University of Virginia Patent Foundation

  公开号：EP3670509A1

  公开（公告）日：2020-06-24

  This invention describes the development of targeted small molecule inhibitors of the inv(16) fusion, the causative agent in ∼12% of acute myeloid leukemia (AML). The inv(16) fusion results in expression of the CBFβ-SMMHC fusion protein in the blood cells of afflicted patients. The present invention provides compounds which inhibit the function of both CBFβ and the CBFβ-SMMHC fusion. These compounds block the growth of an inv(16) leukemia cell line as well as increase its apoptosis, while showing minimal effects against non inv(16) cell lines. As a mechanism to develop inhibitors with selectivity for the CBFβ-SMMHC fusion protein, the present invention further provides dimeric derivatives of these compounds which show both increased potency as well as selectivity for CBFβ-SMMHC. These compounds show potent inhibition of an inv(16) leukemia cell line with minimal effects on non inv(16) cell lines. Analysis of the pharmacokinetics of the developed compounds has made it possible to improve the lifetime of the compound in the plasma of mice to a level commensurate with long-term treatment.

  本发明描述了 inv(16) 融合的靶向小分子抑制剂的开发，inv(16) 融合是 12% 的急性髓性白血病（AML）的致病因子。inv（16）融合会导致患者血细胞中表达 CBFβ-SMMHC 融合蛋白。本发明提供了抑制 CBFβ 和 CBFβ-SMMHC 融合蛋白功能的化合物。这些化合物能阻断inv(16)白血病细胞系的生长，并增加其凋亡，同时对非inv(16)细胞系的影响极小。作为开发对 CBFβ-SMMHC 融合蛋白具有选择性的抑制剂的机制，本发明进一步提供了这些化合物的二聚衍生物，它们对 CBFβ-SMMHC 具有更高的效力和选择性。这些化合物对 inv(16) 白血病细胞系具有强效抑制作用，而对非 inv(16) 细胞系的影响极小。通过对所开发化合物的药代动力学分析，可以将化合物在小鼠血浆中的存活时间延长到与长期治疗相称的水平。