2-(2,4-dihydroxyphenyl)-1H-benzoimidazole-5-carboxylic acid | 1018501-25-1

• 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-(2,4-dihydroxyphenyl)-1H-benzoimidazole-5-carboxylic acid
• 英文别名: 2-(2,4-dihydroxyphenyl)-1H-benzo[d]imidazole-5-carboxylic acid；2,4-Dihydroxy-2-phenyl-1H-benzimidazole-5-carboxylic acid；2-(2,4-dihydroxyphenyl)-3H-benzimidazole-5-carboxylic acid
• CAS: 1018501-25-1
• 化学式: C₁₄H₁₀N₂O₄
• 分子量: 270.244
• InChiKey: JTRRGSLOOQTFAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二氨基苯甲酸 、 2,4-二羟基苯甲醛 在 sodium metabisulfite 、 氯化胆碱 作用下， 以 甘油 为溶剂， 反应 0.5h， 以94%的产率得到2-(2,4-dihydroxyphenyl)-1H-benzoimidazole-5-carboxylic acid
  参考文献：
  名称：

  深共晶溶剂作为合成多奈哌齐类化合物的 2-羟基苯基苯并咪唑基支架的有效反应介质

  摘要：

  最近，基于乙酰胆碱酯酶 (AChE) 抑制剂多奈哌齐 (Donepezil) 的框架，未取代的 2-羟基苯基苯并咪唑被用作一系列杂合体（包括命中化合物 PZ1）的支架，多奈哌齐是一种新的有前景的阿尔茨海默病多靶点配体。 AD) 治疗。基于这些发现，我们现在设计并完成了在所谓的深共熔溶剂 (DESs) 中 PZ1 的整个合成，DESs 已成为绿色合成中一类非常规的生物可再生反应介质。在优化的反应条件下，在DESs中也完善了一系列2-羟基苯基苯并咪唑基核的制备，并提供了与其他使用有毒和挥发性有机溶剂（VOCs）的路线的比较。

  DOI：

  10.3390/molecules25030574

文献信息

• 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。
• Design, synthesis and biological evaluation of novel hydroxy-phenyl-1H-benzimidazoles as radical scavengers and UV-protective agents
  作者：Alessia Bino、Anna Baldisserotto、Emanuela Scalambra、Valeria Dissette、Daniela Ester Vedaldi、Alessia Salvador、Elisa Durini、Stefano Manfredini、Silvia Vertuani

  DOI：10.1080/14756366.2016.1265523

  日期：2017.1.1

  An ever-increasing incidence of skin neoplastic diseases is registered. Therefore, it is important to protect the skin from the UV radiation that reaches the epidermis and dermis but also to block ROS generated by them. Our attention was attracted in developing new compounds provided with both UV filtering and antioxidant capacities. To this end, 2-phenyl-1H-benzimidazole-5-sulfonic acid (PBSA), a known UV filter, was selected as lead compound for its lack of antioxidant activity, high water solubility and good safety profile. PBSA was sequentially modified introducing hydroxyls on the phenyl ring and also substituting the functional group in position 5 of the benzimidazole ring. At the end of the synthetic study, a new, very potent class of antioxidants has been obtained. Surprisingly some of the developed molecules, while devoid of significant UV-filtering activity was endowed with potent UV-filtering booster capability if associated with known commercial UVB and UVA filters.
• DUALISTIC MOLECULES HAVING UV RADIATION FILTRATING ABILITY AT WIDE SPECTRUM AND POTENT DAMPING ACTIVITY OF THE REACTIVITY OF FREE RADICALS (RADICALS SCAVENGING)
  申请人：Università Degli Studi Di Ferrara

  公开号：EP2800741B1

  公开（公告）日：2017-03-15
• US8889881B2
  申请人：——

  公开号：US8889881B2

  公开（公告）日：2014-11-18