2-(3,4-dimethoxyphenyl)-5-methyl-1H-benzo[d]imidazole

• 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-(3,4-dimethoxyphenyl)-5-methyl-1H-benzo[d]imidazole
• 英文别名: 2-(3,4-dimethoxyphenyl)-6-methyl-1H-benzimidazole
• 化学式: C₁₆H₁₆N₂O₂
• mdl: MFCD06312162
• 分子量: 268.315
• InChiKey: BYOSHWCTEYOKIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 3,4-二氨基甲苯 在 sodium meta bi sulfate 作用下， 以 乙醇 、 水 为溶剂， 以90 %的产率得到2-(3,4-dimethoxyphenyl)-5-methyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  N,2,6-三取代1H-苯并咪唑衍生物作为抗菌和抗癌药物的新支架：设计、合成、体外评估和计算机研究

  摘要：

  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

  DOI：

  10.1039/d2ra06667j

文献信息

• Benzimidazoles from Aryl Alkyl Ketones and 2-Amino Anilines by an Iodine Catalyzed Oxidative C(CO)–C(alkyl) Bond Cleavage
  作者：Owk Ravi、Altab Shaikh、Atul Upare、Kiran Kumar Singarapu、Surendar Reddy Bathula

  DOI：10.1021/acs.joc.7b00165

  日期：2017.4.21

  Novel molecular iodine catalyzed cyclization reactions of 2-amino anilines with aryl alkyl ketones under oxidant and metal-free conditions are described. The reaction likely involves sequential C–N bond formation followed by C(CO)–C(alkyl) bond cleavage. Various 2-substituted benzimidazoles are obtained in moderate to good yields in a single step from readily available acetophenones, propiophenones

  描述了在氧化剂和无金属条件下2-氨基苯胺与芳基烷基酮的新型分子碘催化的环化反应。该反应可能涉及顺序形成C–N键，然后裂解C（CO）–C（烷基）键。从容易获得的苯乙酮，苯乙酮和苯乙酮中一步即可以中等到良好的收率获得各种2-取代的苯并咪唑。
• NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR
  申请人：Chung Hae Young

  公开号：US20140037564A1

  公开（公告）日：2014-02-06

  Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

  提供了一种具有美白皮肤、抗氧化和PPAR活性的新化合物及其医药用途，该化合物具有抑制酪氨酸酶的美白皮肤活性，因此适用于用于美白皮肤的药用组合物或化妆品；具有抗氧化活性，因此适用于预防和治疗皮肤衰老；具有PPAR活性，特别是PPARα和PPARγ活性，因此适用于用于预防和治疗肥胖、代谢性疾病或心血管疾病的药用组合物或保健食品。
• NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREOF
  申请人：Pusan National University Industry-University Cooperation Foundation

  公开号：US20150366776A1

  公开（公告）日：2015-12-24

  Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

  提供了一种具有美白、抗氧化和PPAR活性的新化合物及其医疗用途，该化合物具有抑制酪氨酸酶的美白活性，因此可用于美白药物或化妆品产品；具有抗氧化活性，因此可用于预防和治疗皮肤衰老；具有PPAR活性，特别是PPARα和PPARγ活性，因此可用于制备有效预防和治疗肥胖症、代谢性疾病或心血管疾病的药物组合物或保健食品。
• A novel synthesis of 2-arylbenzimidazoles in molecular sieves-MeOH system and their antitubercular activity
  作者：Amit K. Chaturvedi、Amit Kumar Verma、Jay Prakash Thakur、Sudeep Roy、Shashi Bhushan Tripathi、Balagani Sathish Kumar、Sadiya Khwaja、Naresh K. Sachan、Ashok Sharma、Debabrata Chanda、Karuna Shanker、Dharmendra Saikia、Arvind S. Negi

  DOI：10.1016/j.bmc.2018.07.049

  日期：2018.8

  Arylbenzimidazoles have been synthesized as antimycobacterial agents. An efficient synthesis has been developed for 2-arylbenzimidazoles from o-phenylenediamines and aromatic aldehydes in molecular sieves-methanol system. The methodology is straightforward to get 2-arylbenzimidazoles (3a-3z) in excellent yields with high chemoselectivity over 2-aryl-1-benzylbenzimidazoles (4a-4z). All these benzimidazole analogues were evaluated against M. tuberculosis in BACTEC radiometric assay. The compounds 4y and 4z exhibited potential antitubercular activity against M. tuberculosis H (37)Rv, MIC at 16 mu M and 24 mu M respectively. The best compound of the series i.e. compound 4y was well tolerated by Swiss-albino mice in acute oral toxicity. Compound 4y possessing a diarylbenzimidazole core, can further be optimized for better activity.
• Microwave‐Assisted One‐Pot Synthesis of 2‐(Substituted phenyl)‐1<i>H</i>‐benzimidazole Derivatives
  作者：Gabriel Navarrete‐Vázquez、Hermenegilda Moreno‐Diaz、Samuel Estrada‐Soto、Mariana Torres‐Piedra、Ismael León‐Rivera、Hugo Tlahuext、Omar Muñoz‐Muñiz、Hector Torres‐Gómez

  DOI：10.1080/00397910701473325

  日期：2007.8.1