(E)-3-(2,4-dihydroxybenzylidene)pyrrolidine-2,5-dione | 1383603-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-3-(2,4-dihydroxybenzylidene)pyrrolidine-2,5-dione
• 英文别名: (E)-3-(2,4-Dihydroxybenzylidene)pyrrolidine-2,5-dione；(3E)-3-[(2,4-dihydroxyphenyl)methylidene]pyrrolidine-2,5-dione
• CAS: 1383603-25-5
• 化学式: C₁₁H₉NO₄
• 分子量: 219.197
• InChiKey: PTHHGONJHHJYIU-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  triphenylphosphoranylidene succinimide 、 2,4-二羟基苯甲醛 以 甲醇 为溶剂， 反应 24.0h， 以82%的产率得到(E)-3-(2,4-dihydroxybenzylidene)pyrrolidine-2,5-dione
  参考文献：
  名称：

  피부미백, 항산화 및 ＰＰＡＲ 활성을 갖는 신규 화합물 및 이의 의학적 용도

  摘要：

  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。

  公开号：

  KR101677122B1

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。
• Evaluation of in vitro and in vivo anti-melanogenic activity of a newly synthesized strong tyrosinase inhibitor (E)-3-(2,4 dihydroxybenzylidene)pyrrolidine-2,5-dione (3-DBP)
  作者：Ki Wung Chung、Yun Jung Park、Yeon Ja Choi、Min Hi Park、Young Mi Ha、Yohei Uehara、Jung Hyun Yoon、Pusoon Chun、Hyung Ryong Moon、Hae Young Chung

  DOI：10.1016/j.bbagen.2012.03.018

  日期：2012.7

  Background: Tyrosinase inhibitors have become increasingly important because of their ability to inhibit the synthesis of the pigment melanin. A search for new agents with strong tyrosinase activity led to the synthesis of the tyrosinase inhibitor (E)-3-(2,4-dihydroxybenzylidene)pyrrolidine-2,5-dione (3-DBP).Methods: The inhibitory effect of 3-DBP on tyrosinase activity and melanin production was examined in murine melanoma B16F10 cells. Additional experiments were performed using HRM2 hairless mice to demonstrate the effects of 3-DBP in vivo.Results: The novel compound, 3-DBP, showed an inhibitory effect against mushroom tyrosinase (IC50 = 0.53 mu M), which indicated that it was more potent than the well-known tyrosinase inhibitor kojic acid (IC50 =- 8.2 mu M). When tested in B16F10 melanoma cells treated with a-melanocyte stimulating hormone (alpha-MSH), 3-DBP also inhibited murine tyrosinase activity, which in turn induced a decrease in melanin production in these cells. The anti-melanogenic effect of 3-DBP was further verified in HRM2 hairless mice. The skin-whitening index (L value) of HRM2 hairless mice treated with 3-DBP before irradiation with UVB was greater than that of UVB-irradiated mice that were not treated with 3-DBP.General significance: The newly synthesized 3-DBP has a potent inhibitory effect on tyrosinase. In addition to an in vitro investigation of the effects of 3-DBP on tyrosinase, in vivo studies using an HRM2 hairless mouse model demonstrated the anti-melanogenic potency of 3-DBP. Our newly synthesized 3-DBP showed efficient tyrosinase inhibitory effect in vivo and in vitro. Our finding suggests that 3-DBP can be an effective skin-whitening agent. (C) 2012 Elsevier B.V. All rights reserved.
• MAESA JAPONICA EXTRACTS AND METHODS OF USE
  申请人：Avon Products, Inc.

  公开号：EP2790666A2

  公开（公告）日：2014-10-22
• Maesa Japonica Extracts and Methods of Use
  申请人：Avon Products, Inc.

  公开号：US20130149268A1

  公开（公告）日：2013-06-13

  Methods of using extracts of Maesa japonica to impart anti-aging benefits to skin and/or improve skin conditions resulting from aging or damaged skin.