(Z)-5-(3,4,5-trimethoxybenzylidene)imidazolidine-2,4-dione

• 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-(3,4,5-trimethoxybenzylidene)imidazolidine-2,4-dione
• 英文别名: 5-(3,4,5-Trimethoxybenzylidene)-2,4-imidazolidinedione；(5Z)-5-[(3,4,5-trimethoxyphenyl)methylidene]imidazolidine-2,4-dione
• 化学式: C₁₃H₁₄N₂O₅
• 分子量: 278.265
• InChiKey: MIPHJRZSHMVBJB-YWEYNIOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  85.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-5-(3,4,5-trimethoxybenzylidene)imidazolidine-2,4-dione 在 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (Z)-5-(3,4,5-trimethoxybenzylidene)-3-(3-(4-(2-ethoxyphenyl)piperazine-1-yl)propyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  苯哌嗪-乙内酰脲衍生物中α1-肾上腺素能/5-羟色胺受体活性的结构决定因素

  摘要：

  几项研究证实了肾上腺素能和血清素能系统之间的相互作用以及这些现象对焦虑发病机制的影响。因此，寻找具有多功能药效学特征的化学制剂可能会为中枢神经系统疾病带来高效的治疗方法。这项研究提供了对乙内酰脲-芳基哌嗪基团及其血清素/α-肾上腺素能活性的深入结构洞察。新合成的化合物在放射性配体结合试验中进行了测试，并评估了所选衍生物的内在活性。计算机辅助 SAR 分析使我们能够回答有关特定结构片段对选择性活性和多功能活性的影响的问题。根据所进行的研究，有两个主要结构：(a) 化合物12具有多功能肾上腺素能 - 5-羟色胺活性，是一种有希望成为有效抗焦虑剂的候选物；(b) 化合物14具有高 α 1A /α 1D亲和力和对 α 1B 的选择性，由于消除了可能的心脏毒性作用而推荐使用。这项工作的结构结论为未来的先导优化提供了重要支持，以便在寻找新的 CNS 调节剂时实现所需的药效学特征。

  DOI：

  10.3390/molecules26227025
• 作为产物：
  描述：

  海因 、 3,4,5-三甲氧基苯甲醛 在 sodium acetate on alumina 作用下， 反应 0.03h， 以79%的产率得到(Z)-5-(3,4,5-trimethoxybenzylidene)imidazolidine-2,4-dione
  参考文献：
  名称：

  5-亚烷基和5-亚芳基乙内酰脲的微波辅助无溶剂区域特异性合成

  摘要：

  摘要 乙内酰脲已成为一类众所周知的结构，在农用化学品和治疗剂方面有着重要的应用。这种结构基序在合成适合制备潜在生物活性分子的小构件中很重要。从这个意义上说，5-亚烷基和5-亚芳基乙内酰脲构成合成α-氨基酸前体的很好例子。本文报道了这些化合物在绿色化学条件下的微波辅助合成。该方法已证明可提供 74-96% 的产率。

  DOI：

  10.1080/00397910600589007

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。
• 피부미백, 항산화 및 ＰＰＡＲ 활성을 갖는 신규 화합물 및 이의 의학적 용도
  申请人：Pusan National University Industry-University Cooperation Foundation 부산대학교 산학협력단(220040044843) BRN ▼621-82-06530

  公开号：KR101677122B1

  公开（公告）日：2016-11-17

  본 발명은 피부미백, 항산화 및 PPAR 활성을 갖는 신규 화합물 및 이의 의학적 용도에 관한 것으로, 본 발명에 따른 화합물들은 티로시나아제를 억제하는 피부미백 활성을 지니므로 피부미백용 약학조성물 또는 화장품에 유용하게 사용될 수 있고, 항산화 활성을 지니므로 피부노화 등의 예방 또는 치료에 유용하게 사용될 수 있으며, 또한 PPAR 활성 특히, PPARα 및 PPARγ 활성을 지니므로 비만, 대사성 질환 또는 심혈관계 질환을 예방하고 치료하는 데에 유용한 약학조성물 또는 건강식품으로 사용될 수 있다.

  本发明涉及具有皮肤美白、抗氧化和PPAR活性的新化合物及其医学用途，根据本发明的化合物具有抑制酪氨酸酶的皮肤美白活性，因此可用于皮肤美白药物组合物或化妆品中，具有抗氧化活性，因此可用于预防或治疗皮肤老化等，另外，由于具有PPAR活性，特别是具有PPARα和PPARγ活性，因此可用作预防和治疗肥胖、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。
• Analogs of 5-(substituted benzylidene)hydantoin as inhibitors of tyrosinase and melanin formation
  作者：Young Mi Ha、Jin-Ah Kim、Yun Jung Park、Daeui Park、Ji Min Kim、Ki Wung Chung、Eun Kyeong Lee、Ji Young Park、Ji Yeon Lee、Hye Jin Lee、Jeong Hyun Yoon、Hyung Ryong Moon、Hae Young Chung

  DOI：10.1016/j.bbagen.2011.03.001

  日期：2011.6

  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.
• Process for the preparation of dl-beta-aryl amino acids
  申请人：ALKALOIDA VEGYESZETI GYAR

  公开号：EP0156582B1

  公开（公告）日：1988-09-14