2-(3,4-dihydroxyphenyl)-1H-benzoimidazole-5-sulfonic acid | 1446711-39-2

• 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-dihydroxyphenyl)-1H-benzoimidazole-5-sulfonic acid
• 英文别名: 2-(3,4-dihydroxyphenyl)-3H-benzimidazole-5-sulfonic acid
• CAS: 1446711-39-2
• 化学式: C₁₃H₁₀N₂O₅S
• 分子量: 306.299
• InChiKey: JOWAWESDSRCYQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 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：
  132
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-diaminobenzenesulfonic acid sulfate salt 、 3,4-二羟基苯甲醛 在 sodium hydrogensulfite 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 2-(3,4-dihydroxyphenyl)-1H-benzoimidazole-5-sulfonic acid
  参考文献：
  名称：

  DUALISTIC MOLECULES HAVING UV RADIATION FILTRATING ABILITY AT WIDE SPECTRUM AND POTENT DAMPING ACTIVITY OF THE REACTIVITY OF FREE RADICALS (RADICAL SCAVENGING)

  摘要：

  具有结构2-苯基苯并咪唑的化合物I及/或其药学上可接受的盐，其中化合物I的结构如下： 其中n为1、2或3，R为羧基(—COOH)或磺酸基(—SO3H)；包括该化合物的药物和/或化妆品配方和/或医疗器械；以及合成该化合物的方法。

  公开号：

  US20140363386A1

文献信息

• 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.
• [EN] DUALISTIC MOLECULES HAVING UV RADIATION FILTRATING ABILITY AT WIDE SPECTRUM AND POTENT DAMPING ACTIVITY OF THE REACTIVITY OF FREE RADICALS (RADICALS SCAVENGING)<br/>[FR] NOUVELLES MOLÉCULES À DOUBLE FONCTION AYANT UNE CAPACITÉ DE FILTRATION DU RAYONNEMENT UV SUR UN LARGE SPECTRE ET UNE PUISSANTE ACTIVITÉ D'ATTÉNUATION DE LA RÉACTIVITÉ DE RADICAUX LIBRES (PIÉGEAGE DE RADICAUX)
  申请人：UNIV FERRARA

  公开号：WO2013102843A3

  公开（公告）日：2013-09-19
• NEW 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：EP2800741A2

  公开（公告）日：2014-11-12
• 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
• [EN] NEW DUALISTIC MOLECULES HAVING UV RADIATION FILTRATING ABILITY AT WIDE SPECTRUM AND POTENT DAMPING ACTIVITY OF THE REACTIVITY OF FREE RADICALS (RADICALS SCAVENGING)<br/>[FR] NOUVELLES MOLÉCULES À DOUBLE FONCTION AYANT UNE CAPACITÉ DE FILTRATION DU RAYONNEMENT UV SUR UN LARGE SPECTRE ET UNE PUISSANTE ACTIVITÉ D'ATTÉNUATION DE LA RÉACTIVITÉ DE RADICAUX LIBRES (PIÉGEAGE DE RADICAUX)
  申请人：UNIV FERRARA

  公开号：WO2013102843A2

  公开（公告）日：2013-07-11

  Compound with structure 2-phenylbenzimidazole of formula I and/or a pharmaceutically acceptable salt thereof, wherein said compound of formula I corresponds to: in which n is 1, 2 or 3 and in which R is a carboxyl radical (-COOH) or a sulphonic radical (-S03H); pharmaceutical and/or cosmetic formulation and/or medical device comprising such a compound; method for synthesising it.