(Z)-5-(2-hydroxybenzylidene)imidazolidine-2,4-dione | 90771-20-3

• 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-(2-hydroxybenzylidene)imidazolidine-2,4-dione
• 英文别名: 5-Salicylidenehydantoin；(5Z)-5-[(2-hydroxyphenyl)methylidene]imidazolidine-2,4-dione
• CAS: 90771-20-3；139554-59-9；137920-40-2
• 化学式: C₁₀H₈N₂O₃
• 分子量: 204.185
• InChiKey: GXPDYJIBYGLMKU-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  靛红 、 (Z)-5-(2-hydroxybenzylidene)imidazolidine-2,4-dione 、 2-氨基-2-苯基乙酸 以 甲醇 为溶剂， 以91 %的产率得到(2’R*,4S*,4’S*,5’R*)-4'-(2-hydroxyphenyl)-5'-phenyldispiro[imidazolidine-4,3'-pyrrolidine-2',3''-indoline]-2,2'',5-trione
  参考文献：
  名称：

  四环螺吲哚并吡咯烷接枝乙内酰脲支架的合成：晶体学分析、分子对接研究及其抗菌、抗炎和镇痛活性评价

  摘要：

  在持续寻找具有多谱治疗应用的新型潜在候选药物的过程中，通过靛红衍生物、2-苯基甘氨酸和多种亚芳基-咪唑烷-2,4-二酮（乙内酰脲）之间的区域选择性三组分反应，设计并合成了一系列新型螺吲哚。 。通过 X 射线衍射研究和 NMR 光谱法确定了建议的立体化学。筛选所得四环杂环化合物的体外和体内抗炎和镇痛活性及其体外抗菌效力。体外抗菌筛选表明，几种衍生物对不同目标微生物表现出显着的生长抑制作用。与参比药物四环素 (MIC = 500 µg/mL) 相比，所有测试化合物均表现出优异的抗藤黄微球菌菌株活性 (93.75 µg/mL ≤ MIC ≤ 375 µg/mL)。与两性霉素 B（MIC = 31.25 和 62.50）相比，吡咯烷环上带有对氯苯基的化合物 4e 对白色念珠菌和克柔念珠菌表现出最大的抗真菌潜力（MIC 值分别为 23.43 µg/mL 和 46.87 µg/mL）分别为 µg/mL）。目标化合物还针对脂氧合酶

  DOI：

  10.3390/molecules28217443
• 作为产物：
  描述：

  对羟基苯甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (Z)-5-(2-hydroxybenzylidene)imidazolidine-2,4-dione
  参考文献：
  名称：

  基于乙内酰脲的分子光电开关

  摘要：

  描述了基于芳基乙内酰脲的分子光开关的新家族及其合成以及光化学和光物理研究。已使用简单和通用的化学方法以高收率将一系列乙内酰脲衍生物制备为单一异构体。我们的研究表明，可以通过诸如光源或滤光片等外部因素轻松控制这些化合物的光稳态。此外，详细的研究证明这些开关是有效的（即，它们有效利用了光能，具有很高的抗疲劳性，并且非常耐光）。在一些情况下，交换机可以完全关上/关，特定应用程序的理想功能。还进行了一系列理论计算以了解分子水平上的光异构化机理。

  DOI：

  10.1021/acs.joc.5b00244

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。
• Diethyl 2,4-dioxoimidazolidine-5-phosphonates: Horner-Wadsworth-Emmons reagents for the mild and efficient preparation of C-5 unsaturated hydantoin derivatives
  作者：Nicholas A. Meanwell、Herbert R. Roth、Edward C. R. Smith、Donald L. Wedding、J. J. Kim Wright

  DOI：10.1021/jo00024a036

  日期：1991.11

  The phosphonates 19 and 20 were prepared from hydantoin and 1-methylhydantoin, respectively, by way of bromination at C-5 and a subsequent Michaelis-Arbuzov reaction with triethyl phosphite. The Horner-Wadsworth-Emmons-type reagents 19 and 20 were found to react readily with aromatic and aliphatic aldehydes, in the presence of a base, to produce C-5 unsaturated hydantoin derivatives 22 and 26, generally in high yield. The products 22 and 26 were frequently isolated as mixtures of E and Z isomers depending upon the identity of the aldehyde and phosphonate. The isomeric configuration of the products was determined from an analysis of NMR spectral data. Long-range C-13-H-1 coupling constants between the C-4 carbonyl of the hydantoin ring and the olefinic proton were found to be diagnostic of isomer geometry. Conditions were also developed that allowed coupling of 19 and 20 with cyclic and acyclic ketones and alpha-dicarbonyl compounds to afford the corresponding olefinic products. C-5 unsaturated hydantoin derivatives are of synthetic utility as precursors to alpha-amino acid derivatives, pyruvates, and the imidazo[4,5-b]quinolin-2-one heterocyclic ring system, a class of potent inhibitors of low Km cAMP phosphodiesterase and the chromophore present in the siderophore azotobactin.
• 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.