1α-(羟甲基)-25-羟基维生素D3 | 174533-99-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1α-(羟甲基)-25-羟基维生素D3
• 英文名称: 2-(3,4-dihydroxyphenyl)-1H-benzo[d]imidazole-5-carboxylic acid
• 英文别名: 2-(3,4-dihydroxyphenyl)-1H-benzoimidazole-5-carboxylic acid；2-(3,4-dihydroxyphenyl)-1H-benzimidazole-5-carboxylic acid；3,4-Dihydroxy-2-phenyl-1H-benzimidazole-5-carboxylic acid；2-(3,4-dihydroxyphenyl)-3H-benzimidazole-5-carboxylic acid
• CAS: 174533-99-4
• 化学式: C₁₄H₁₀N₂O₄
• 分子量: 270.244
• InChiKey: UDYQXHVPYOHLJN-UHFFFAOYSA-N

物化性质

• 沸点：
  660.1±65.0 °C(Predicted)
• 密度：
  1.591±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：

  3,4-二羟基苯甲醛 、 3,4-二氨基苯甲酸 在 sodium metabisulfite 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以81%的产率得到1α-(羟甲基)-25-羟基维生素D3
  参考文献：
  名称：

  2-芳基苯并咪唑类化合物的合成及抗氧化剂和抗增殖活性的评估。

  摘要：

  简单地合成了三个系列的芳基苯并咪唑衍生物3-40、45，并测试了它们的抗氧化能力。通过DPPH，FRAP和ORAC测试测试了2-芳基苯并咪唑类对各种自由基的影响，并显示了不同的活性曲线。已经观察到2-芳基部分上的羟基的数量和位置以及二乙氨基或2-苯乙烯基的存在与良好的抗氧化能力有关。此外，与市售PBSA滤光片相比，苯并咪唑在体外显示令人满意的SPF值，证明具有良好的光保护特性。特别地，2-芳基苯并咪唑-5-磺酸15和38、2-苯乙烯基-苯并咪唑45显示出针对UVA和UVB射线的广谱日光防护。测试了苯并咪唑对人皮肤黑色素瘤Colo-38细胞的抗增殖作用。苯乙烯基苯并咪唑45在低微摩尔浓度下对Colo-38细胞具有抗增殖作用，对正常的HaCat角质形成细胞具有极低的抗增殖活性。

  DOI：

  10.1016/j.bioorg.2019.103396

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
• Dendrimer compound and organic luminescent device employing the same
  申请人：Kitano Makoto

  公开号：US20070154732A1

  公开（公告）日：2007-07-05

  A dendrimer compound characterized by comprising a core represented by the following formula (1-1), (1-2), (1-3), or (1-4) and at least one kind of dendritic structure selected among dendritic structures represented by the following formulae (3) and (4).