(Z)-5-(3-ethoxy-4-hydroxybenzylidene)imidazolidine-2,4-dione | 1312438-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (Z)-5-(3-ethoxy-4-hydroxybenzylidene)imidazolidine-2,4-dione
• 英文别名: (5Z)-5-[(3-ethoxy-4-hydroxyphenyl)methylidene]imidazolidine-2,4-dione
• CAS: 1312438-15-5
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: CPMPTNJRSLMXKO-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴乙酸 、 (Z)-5-(3-ethoxy-4-hydroxybenzylidene)imidazolidine-2,4-dione 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Polyoligopeptides functionalized zinc(II)porphyrins: Step towards artificial hemes

  摘要：

  利用叠氮化物和含乙炔基的前体，通过点击化学反应制备了两种新的锌(II)卟啉寡肽共轭物（锌(II)-5,10,15,20-双[4-(肽)-苯基]卟啉（5）和-四[3,5-二(肽)苯基]卟啉（9；肽=-CH2(CO)Gly-Phe-Ala-CNH2）。其光谱特征（S0→S1 和瞬态 T1→Tn 吸收、激发和发射光谱）是典型的卟啉锌(II)，在锚定寡肽后未显示出任何扰动，但光物理参数（𝜏F 和 ΦF）略有下降，T1 寿命也有较大下降，这可归因于已知的 "松动螺栓 "效应。利用计算机建模和使用 C60 作为光氧化剂比较 5 和 9 的双分子荧光淬灭速率常数，对溶液中 9 的结构进行了定性分析。在 C60 方法中，5 表现出完全可访问的锌(II)卟啉单元，而 9 则表现出较慢的淬灭速率常数，这意味着必须存在一些立体阻碍。

  DOI：

  10.1142/s1088424611003756
• 作为产物：
  描述：

  乙基香兰素 、 海因 在 哌啶 作用下， 反应 0.5h， 以79%的产率得到(Z)-5-(3-ethoxy-4-hydroxybenzylidene)imidazolidine-2,4-dione
  参考文献：
  名称：

  Analogs of 5-(substituted benzylidene)hydantoin as inhibitors of tyrosinase and melanin formation

  摘要：

  Background: Many tyrosinase inhibitors find application in cosmetics and pharmaceutical products for the prevention of the overproduction of melanin in the epidermis. A series of 5-(substituted benzylidene) hydantoin derivatives 2a-2k were prepared, and their inhibitory activities toward tyrosinase and melanin formation were evaluated.Methods: The structures of the compounds were established using H-1 and C-13 NMR spectroscopy and mass spectral analyses. All the synthesized compounds were evaluated for their mushroom tyrosinase inhibition activity.Results: The best results were obtained for compound 2e which possessed hydroxyl group at R-2 and methoxy group at R-3, respectively. We predicted the tertiary structure of tyrosinase, simulated its docking with compound 2e and confirmed that this compound interacts strongly with mushroom tyrosinase residues as a competitive tyrosinase inhibitor. In addition, we found that 2e inhibited melanin production and tyrosinase activity in B16 cells.Conclusions: Compound 2e could be considered as a promising candidate for preclinical drug development in skin hyperpigmentation applications.General significance: This study will enhance understanding of the mechanism of tyrosinase inhibition and will contribute to the development of effective drugs for use hyperpigmentation. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bbagen.2011.03.001

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：US20140023603A1

  公开（公告）日：2014-01-23

  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疗用途，该化合物具有美白皮肤的活性，可抑制酪氨酸酶，因此适用于用于美白皮肤的药物组合物或化妆品；具有抗氧化活性，因此适用于预防和治疗皮肤老化；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物组合物或保健食品。
• 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：US20160102065A1

  公开（公告）日：2016-04-14

  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组合物或化妆品产品；具有抗氧化活性，因此可用于预防和治疗皮肤老化；具有PPAR活性，特别是PPARα和PPARγ活性，因此可用于有效预防和治疗肥胖症、代谢疾病或心血管疾病的药物组合物或保健食品。
• US9216148B2
  申请人：——

  公开号：US9216148B2

  公开（公告）日：2015-12-22
• US9896421B2
  申请人：——

  公开号：US9896421B2

  公开（公告）日：2018-02-20