(5Z)-5-(2-hydroxybenzylidene)-1,3-thiazolidine-2,4-dione | 6325-94-6

• 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: (5Z)-5-(2-hydroxybenzylidene)-1,3-thiazolidine-2,4-dione
• 英文别名: (5E)-5-[(2-hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 6325-94-6
• 化学式: C₁₀H₇NO₃S
• 分子量: 221.236
• InChiKey: IZVVCHFDGJEVTB-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 水杨醛 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.25h， 以95%的产率得到(5Z)-5-(2-hydroxybenzylidene)-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Tetrabutylammonium bromide and K₂CO₃: an eco-benign catalyst for the synthesis of 5-arylidene-1,3-thiazolidine- 2,4-diones via Knoevenagel condensation

  摘要：

  Phase-transfer catalyzed, energy-efficient and facile synthesis of 5-arylidene-1,3-thiazolidine-2,4-diones was developed. Three independent variables (temperature, bases and phase-transfer catalyst (PTC)) were screened through one-factor-at-a time (OFAT) study. The optimum reaction conditions suggested by the OFAT analysis were the use of tetrabutylammonium bromide (8 mol%) and potassium carbonate (1 mmol) for the reaction at 100 degrees C. The nitrogen of PTC stabilizes carbonyl groups of thiazolidine-2,4-dione (TZD). The active methylene hydrogen of TZD forms potassium salt with potassium carbonate and generates 5-arylidene-1,3-thiazolidine-2,4-diones (1-16) through nucleophilic attack on the carbonyl carbon of arylaldehydes. The prominent advantages of this new process are economic viability, shorter reaction time (15 min), simple product isolation (non-chromatographic method), good to excellent yields (78-96%) and solvent-free conditions.

  DOI：

  10.1080/17415993.2014.970555

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。
• Benzylidene-1,3-thiazolidine-2,4-dione compounds for promoting and/or inducing and/or stimulating the pigmentation of keratin materials and/or for limiting their depigmentation and/or whitening
  申请人：Boulle Christophe

  公开号：US20070071699A1

  公开（公告）日：2007-03-29

  The benzylidene-1,3-thiazolidine-2,4-dione compounds having the structural formula (I), or salt and/or solvate and/or isomer thereof: are useful active agents for promoting and/or inducing and/or stimulating the pigmentation of keratin materials and/or preventing and/or limiting the depigmentation and/or bleaching thereof, particularly of human head hair, beard hair, moustache hair, eyelashes and eyebrows, and advantageously are active agents for preventing and/or limiting the canities of human keratin fibers.

  具有结构式（I）或其盐和/或溶剂和/或异构体的苯甲醛基-1,3-噻唑啉-2,4-二酮化合物是促进和/或诱导和/或刺激角蛋白质材料的色素沉淀和/或预防和/或限制其褪色和漂白的有用活性剂，特别是人类头发、胡须、胡子、睫毛和眉毛，优点是预防和/或限制人类角蛋白质纤维的白发。
• 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。
• A CONVENIENT SYNTHESIS OF 5-ARYLIDENETHIAZOLIDINE-2,4-DIONES ON POTASSIUM FLUORIDE-ALUMINIUM OXIDE
  作者：De-Hong Yang、Ben-Yong Yang、Zhen-Chu Chen、Song-Ying Chen

  DOI：10.1080/00304940609355982

  日期：2006.2
• Synthesis of O-prenylated and O-geranylated derivatives of 5-benzylidene2,4-thiazolidinediones and evaluation of their free radical scavenging activity as well as effect on some phase II antioxidant/detoxifying enzymes
  作者：Sk. Ugir Hossain、Sudin Bhattacharya

  DOI：10.1016/j.bmcl.2006.12.040

  日期：2007.3

  A series of 5-arylidene-2,4-thiazolidinediones and its geranyloxy or prenyloxy derivative were synthesized and studied for their radical scavenging activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Their comparable scavenging activities were expressed as IC50 value. Compounds 2c, 2d, 4d, and 6a showed appreciable radical scavenging activities. The vanillin based thiazolidinedione compound 2c displayed highest activity comparable to that of alpha-tocopherol. But in vivo, compound 6a showed better results in inducing phase II detoxifying/antioxidative enzyme.