(Z)-5-(3,5-dihydroxybenzylidene)thiazolidine-2,4-dione | 1362738-30-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (Z)-5-(3,5-dihydroxybenzylidene)thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[(3,5-dihydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1362738-30-4
• 化学式: C₁₀H₇NO₄S
• 分子量: 237.236
• InChiKey: KEJUIGFLSJQLDE-BAQGIRSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-5-(3,5-dihydroxybenzylidene)thiazolidine-2,4-dione 、 溴乙酸乙酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以60%的产率得到(Z)-ethyl 2-(5-(3,5-dihydroxybenzylidene)-2,4-dioxothiazolidin-3-yl)acetate
  参考文献：
  名称：

  2,4-噻唑烷二酮衍生物作为能够调节 BAG3 蛋白的新型抗癌剂的结构优化

  摘要：

  多结构域 BAG3 蛋白是 BAG（Bcl-2 相关的 athanogene）共伴侣家族的成员，参与对许多关键细胞途径至关重要的广泛的蛋白质-蛋白质相互作用，包括自噬、细胞骨架动力学和细胞凋亡。BAG3 的基础表达在几种肿瘤细胞系中升高，它通过与许多蛋白质伙伴的相互作用促进细胞存活信号传导和细胞凋亡抗性。此外，它作为癌症的几个标志的关键角色，如转移、血管生成、自噬激活和细胞凋亡抑制，已经确定。由于参与恶性转化，BAG3已成为控制多种癌症相关信号通路的潜在且有效的生物靶点。最近，通过使用多学科方法，我们报告了第一个干扰其 BAG 结构域 (BD) 的合成 BAG3 调节剂，该调节剂基于 2,4-噻唑烷二酮支架并具有显着的抗增殖活性。在这里，进行了基于 2,4-噻唑烷二酮的化合物的进一步计算机驱动选择。由于简单的合成、对 BAG3BD 结构域的相关结合亲和力和有吸引力的生物活性，这种新一代化合物对于开发进一步的

  DOI：

  10.3390/molecules27030665
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 3,5-二羟基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 以80%的产率得到(Z)-5-(3,5-dihydroxybenzylidene)thiazolidine-2,4-dione
  参考文献：
  名称：

  2,4-噻唑烷二酮衍生物作为能够调节 BAG3 蛋白的新型抗癌剂的结构优化

  摘要：

  多结构域 BAG3 蛋白是 BAG（Bcl-2 相关的 athanogene）共伴侣家族的成员，参与对许多关键细胞途径至关重要的广泛的蛋白质-蛋白质相互作用，包括自噬、细胞骨架动力学和细胞凋亡。BAG3 的基础表达在几种肿瘤细胞系中升高，它通过与许多蛋白质伙伴的相互作用促进细胞存活信号传导和细胞凋亡抗性。此外，它作为癌症的几个标志的关键角色，如转移、血管生成、自噬激活和细胞凋亡抑制，已经确定。由于参与恶性转化，BAG3已成为控制多种癌症相关信号通路的潜在且有效的生物靶点。最近，通过使用多学科方法，我们报告了第一个干扰其 BAG 结构域 (BD) 的合成 BAG3 调节剂，该调节剂基于 2,4-噻唑烷二酮支架并具有显着的抗增殖活性。在这里，进行了基于 2,4-噻唑烷二酮的化合物的进一步计算机驱动选择。由于简单的合成、对 BAG3BD 结构域的相关结合亲和力和有吸引力的生物活性，这种新一代化合物对于开发进一步的

  DOI：

  10.3390/molecules27030665

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。
• Design and synthesis of 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives as novel tyrosinase inhibitors
  作者：Young Mi Ha、Yun Jung Park、Jin-Ah Kim、Daeui Park、Ji Young Park、Hye Jin Lee、Ji Yeon Lee、Hyung Ryong Moon、Hae Young Chung

  DOI：10.1016/j.ejmech.2012.01.019

  日期：2012.3

  In continuing our search for novel tyrosinase inhibitors, a series of 5-(substituted benzylidene)thiazolidine-2,4-diones were rationally designed and synthesized, and their inhibitory effects on mushroom tyrosinase activity were evaluated. Twelve target compounds 2a-2l were designed and synthesized based on the structural characteristics of N-phenylthiourea, a tyrosinase inhibitor, and tyrosine and L-DOPA, the natural substrates of tyrosinase. Among them, (Z)-5-(4-hydroxybenzylidene)thiazolidine-2,4-dione (2a) and (Z)-5-(3-hydroxy-4-methoxybenzylidene)thiazolidine-2,4-dione (2f) exhibited much higher tyrosinase inhibitory activities, with IC50 values of 13.36 and 9.87 mu M, respectively, than kojic acid (IC50 = 24.72 mu M). Kinetic analysis of tyrosinase inhibition revealed that 2a and 2f are competitive inhibitors of mushroom tyrosinase. In addition, through prediction of the potato catechol oxidase tertiary structure and simulation of docking with compounds 2a and 2f using DOCK6, we found that these inhibitors likely bind to the active site of the enzyme. Docking simulation results suggested that 2a and 2f have high binding affinities with potato catechol oxidase. In addition, compounds 2a and 2f effectively inhibited tyrosinase activity and reduced melanin levels in 816 cells treated with alpha-melanocyte-stimulating hormone (alpha-MSH). These data strongly suggest that compounds 2a and 21 suppress the production of melanin via the inhibition of tyrosinase activity. (C) 2012 Elsevier Masson SAS. All rights reserved.
• US9216148B2
  申请人：——

  公开号：US9216148B2

  公开（公告）日：2015-12-22