2-(2',5'-dimethoxyphenyl)-5,6-dimethyl-1H-benzimidazole | 1078708-82-3

• 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: 2-(2',5'-dimethoxyphenyl)-5,6-dimethyl-1H-benzimidazole
• 英文别名: 2-(2,5-dimethoxyphenyl)-5,6-dimethyl-1H-benzimidazole
• CAS: 1078708-82-3
• 化学式: C₁₇H₁₈N₂O₂
• 分子量: 282.342
• InChiKey: MXBADKARIHXJED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2',5'-dimethoxyphenyl)-5,6-dimethyl-1H-benzimidazole 、 间硝基苯甲酰氯 在 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到(2-(2,5-dimethoxyphenyl)-5,6-dimethyl-1H-benzo[d]-imidazol-1-yl)(3-nitrophenyl)methanone
  参考文献：
  名称：

  针对大麻素受体 1 型的苯并咪唑衍生物的设计、合成、生物学评价和结合模式建模

  摘要：

  基于大麻素受体1型（CB1）配体的CoMFA模型设计了一系列N-酰基-2,5-二甲氧基苯基-1H-苯并咪唑。合成化合物并进行放射性配体结合亲和力测定。八种新型苯并咪唑对 CB1 受体在纳摩尔范围内表现出亲和力，与 CP55,940 相比，最有前途的衍生化合物 5 显示出 1.2 nM 的 Ki 值。这些结果证实了我们之前报道的关于苯并咪唑衍生物的 QSAR 模型，为开发具有高 CB1 亲和力的小分子提供了新信息。

  DOI：

  10.1002/ardp.201400201
• 作为产物：
  描述：

  4，5-二甲基-1，2-苯二胺 、 2,5-二甲氧基苯甲醛 以 乙醇 为溶剂， 反应 24.0h， 生成 2-(2',5'-dimethoxyphenyl)-5,6-dimethyl-1H-benzimidazole
  参考文献：
  名称：

  针对大麻素受体 1 型的苯并咪唑衍生物的设计、合成、生物学评价和结合模式建模

  摘要：

  基于大麻素受体1型（CB1）配体的CoMFA模型设计了一系列N-酰基-2,5-二甲氧基苯基-1H-苯并咪唑。合成化合物并进行放射性配体结合亲和力测定。八种新型苯并咪唑对 CB1 受体在纳摩尔范围内表现出亲和力，与 CP55,940 相比，最有前途的衍生化合物 5 显示出 1.2 nM 的 Ki 值。这些结果证实了我们之前报道的关于苯并咪唑衍生物的 QSAR 模型，为开发具有高 CB1 亲和力的小分子提供了新信息。

  DOI：

  10.1002/ardp.201400201

文献信息

• PEG-mediated catalyst-free expeditious synthesis of 2-substituted benzimidazoles and bis-benzimidazoles under solvent-less conditions
  作者：Chhanda Mukhopadhyay、Pradip Kumar Tapaswi

  DOI：10.1016/j.tetlet.2008.08.041

  日期：2008.10

  A wide variety of 2-substituted benzimidazoles and bis-benzimidazoles were synthesized in high yields by PEG-mediated catalyst-free synthesis under solvent-less conditions. The products were directly recrystallized from hot methanol. The reaction occurred giving excellent yields with low as well as high molecular weight PEGs.

  在无溶剂条件下，通过PEG介导的无催化剂合成，可以高收率合成各种2-取代的苯并咪唑和双-苯并咪唑。产物从热甲醇中直接重结晶。发生反应后，无论是低分子量还是高分子量PEG，均具有出色的收率。
• Solid Phase Synthesis of Biologically active Benzimidazole Derivatives Catalysed by CH3 SO3 H-SiO2 Under Solvent free Condition
  作者：Arup Datta、Sanjay Roya

  DOI：10.13005/ojc/360325

  日期：2020.6.30

  A simple an expeditious method was established for the synthesis of 2-Substituted-1H-Benzimidazole derivatives at 90 degrees C using o-phenylenediamine and different aldehydes. It has been found that a mixture of Methanesulphonic acid-SiO2 to be an effective catalyst to generate moderate to high yield of a wide variety of 2-substituted benzimidazole derivatives through a simple workup process. Solid phase, rapid reaction, solvent free technique and simplicity of the reaction procedure are the advantages of this protocol.
• Design, Synthesis, Biological Evaluation and Binding Mode Modeling of Benzimidazole Derivatives Targeting the Cannabinoid Receptor Type 1
  作者：Christian Espinosa-Bustos、Carlos F. Lagos、Javier Romero-Parra、Ana M. Zárate、Jaime Mella-Raipán、Hernán Pessoa-Mahana、Gonzalo Recabarren-Gajardo、Patricio Iturriaga-Vásquez、Ricardo A. Tapia、C. David Pessoa-Mahana

  DOI：10.1002/ardp.201400201

  日期：2015.2

  A series of N‐acyl‐2,5‐dimethoxyphenyl‐1H‐benzimidazoles were designed based on a CoMFA model for cannabinoid receptor type 1 (CB1) ligands. Compounds were synthesized and radioligand binding affinity assays were performed. Eight novel benzimidazoles exhibited affinity for the CB1 receptor in the nanomolar range, and the most promising derivative compound 5 displayed a Ki value of 1.2 nM when compared

  基于大麻素受体1型（CB1）配体的CoMFA模型设计了一系列N-酰基-2,5-二甲氧基苯基-1H-苯并咪唑。合成化合物并进行放射性配体结合亲和力测定。八种新型苯并咪唑对 CB1 受体在纳摩尔范围内表现出亲和力，与 CP55,940 相比，最有前途的衍生化合物 5 显示出 1.2 nM 的 Ki 值。这些结果证实了我们之前报道的关于苯并咪唑衍生物的 QSAR 模型，为开发具有高 CB1 亲和力的小分子提供了新信息。
• Vanadyl Acetylacetonate-Copper (II) Trifluoro Methane Sulfonate Catalyzed Eco-friendly Synthesis of Substituted Benzimidazoles in Aqueous Media
  作者：Samiran Halder

  DOI：10.13005/ojc/360413

  日期：2020.8.28

  Various substituted benzimidazoles have been successfully synthesized in aqueous medium by developing VO(acac)(2)-Cu(OTf)(2) catalytic system. A green synthetic protocol has been created in presence of water and cetyltrimethyl ammonium bromide (CTAB) system in an organic solvent free condition. This chemoselective cyclocondensation cumoxidation process occurred in aqueous media. In this suitable method easily synthesized 2-Substituted benzimidazoles with good yields and no 1,2-disubstituted by-products were noticed. Excellent yields, environmentally benign and mild reaction condition, easy purification of the desired products are the main attractive features of this newly devised method.[GRAPHICS]