5-(3-hydroxy-4-methoxybenzylidene) thiazolidine-2, 4-dione | 184840-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(3-hydroxy-4-methoxybenzylidene) thiazolidine-2, 4-dione
• 英文别名: 2,4-Thiazolidinedione, 5-[(3-hydroxy-4-methoxyphenyl)methylene]-；5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 184840-76-4
• 化学式: C₁₁H₉NO₄S
• 分子量: 251.263
• InChiKey: MHRJJGJJVMGLRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  260 °C
• 密度：
  1.500±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3-hydroxy-4-methoxybenzylidene) thiazolidine-2, 4-dione 、 2-氯-N-(4-乙氧基苯基)乙酰胺 在 三乙胺 作用下， 以 乙腈 为溶剂， 以79.8%的产率得到2-(5-(3-hydroxy-4-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl)-N-(4-ethoxyphenyl) acetamide
  参考文献：
  名称：

  基于N-取代噻唑烷二酮衍生物的醛糖还原酶非羧酸抑制剂

  摘要：

  为了寻找双重活性的 PPAR 调节剂/醛糖还原酶 (ALR2) 抑制剂，研究了 16 种亚苄基噻唑烷二酮衍生物（之前报道为部分 PPARγ 激动剂）以及另外 18 种结构同源物的醛糖还原酶抑制活性。虽然没有化合物具有双重特性，但我们的努力导致了有前途的 ALR2 抑制剂的鉴定。 33 种化合物库中的8 种化合物（ 11、15-16、20-24、30 ）被鉴定为ALR2的有效和选择性抑制剂。化合物21是最有效和选择性的抑制剂，针对ALR2和醛还原酶(ALR1)的IC 50值分别为0.95±0.11和13.52±0.81μM。进行分子对接和动力学研究，以了解决定效力和选择性的分子水平上的抑制剂-酶相互作用。对化合物21进行了进一步的计算机模拟和体外研究，以评估其药代动力学特征。由于酸性较低（p Ka = 9.8），该化合物可能具有优异的质膜渗透性并到达胞质 ALR2。这一事实加上出色的药物相似

  DOI：

  10.1016/j.ejmech.2021.113630
• 作为产物：
  描述：

  异香兰素 、 2,4-噻唑烷二酮 在 1,1'-(propane-1,3-diyl)bis(3-methyl-1H-imidazol-3-ium) dibromide 作用下， 反应 2.0h， 以85%的产率得到5-(3-hydroxy-4-methoxybenzylidene) thiazolidine-2, 4-dione
  参考文献：
  名称：

  Dicationic Ionic Liquid Mediated Synthesis of 5-Arylidine-2,4-thiazolidinediones

  摘要：

  AbstractAn efficient synthesis of 5‐arylidine‐2,4‐thiazolidinediones has been developed using dicationic ionic liquid as green medium and catalyst. This method performed well for the condensation of both aryl as well as heteryl aldehydes with 2,4‐thiazolidinedione and gave 5‐arylidine‐2,4‐thiazolidinediones with excellent yields.

  DOI：

  10.1002/cjoc.201190192

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
• Dicationic Ionic Liquid Mediated Synthesis of 5-Arylidine-2,4-thiazolidinediones
  作者：Dhanaji V. Jawale、Umesh R. Pratap、Dinesh L. Lingampalle、Ramrao A. Mane

  DOI：10.1002/cjoc.201190192

  日期：2011.5

  AbstractAn efficient synthesis of 5‐arylidine‐2,4‐thiazolidinediones has been developed using dicationic ionic liquid as green medium and catalyst. This method performed well for the condensation of both aryl as well as heteryl aldehydes with 2,4‐thiazolidinedione and gave 5‐arylidine‐2,4‐thiazolidinediones with excellent yields.