(E)-5-(4-fluorobenzylidene)thiazolidine-2,4-dione

• 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: (E)-5-(4-fluorobenzylidene)thiazolidine-2,4-dione
• 英文别名: 5-(4-Fluorobenzylidene)thiazolidine-2,4-dione；(5E)-5-[(4-fluorophenyl)methylidene]-1,3-thiazolidine-2,4-dione
• 化学式: C₁₀H₆FNO₂S
• 分子量: 223.228
• InChiKey: XQEXVSOHLCLCFH-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  71.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-5-(4-fluorobenzylidene)thiazolidine-2,4-dione 、 2-[N-甲基-N-(2-吡啶基)氨基]乙醇 在 碘 、 potassium carbonate 、 magnesium 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 罗格列酮
  参考文献：
  名称：

  An alternative synthetic route for an antidiabetic drug, rosiglitazone

  摘要：

  A convenient and scalable four-step novel route has been developed for the synthesis of rosiglitazone (8), an antidiabetic drug. This multistep route requires 4-fluoro benzaldehyde (4), 2,4-thiazolidinedione (6) and 2-chloro pyridine (1) as key reactants and gives overall better yield of rosiglitazone. In addition, some steps have been accelerated, which leads to an overall time saving of 10 h. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.020
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 对氟苯甲醛 在 哌啶 、 silica gel 、 溶剂黄146 作用下， 反应 0.12h， 以87%的产率得到(E)-5-(4-fluorobenzylidene)thiazolidine-2,4-dione
  参考文献：
  名称：

  微波诱导的噻唑烷-2,4-二酮基序合成及5-亚苄基-噻唑烷-2,4-二酮和5-亚苄基-2-硫代-噻唑烷-4-one化合物的高效无溶剂固相平行合成

  摘要：

  开发了一种新型的微波诱导方法，用于在溶剂相条件下合成噻唑烷-2,4-二酮基序。此外，我们报告了一种高效，微波辅助的方法，可在固相和无溶剂条件下平行合成生物学上重要的5-亚苄基-噻唑烷-2,4-二酮和5-亚苄基-2-噻吩并噻唑烷-4-酮化合物。描述了已开发的微波方法与常规方法之间的比较研究。我们还说明了背后的可能机制，以解决哌啶，乙酸和硅胶增强Knoevenagel缩合反应的原因。

  DOI：

  10.1002/jhet.5570430413

文献信息

• Pyrimidine-thiazolidinone derivatives
  申请人：UNITED ARAB EMIRATES UNIVERSITY

  公开号：US10689374B1

  公开（公告）日：2020-06-23

  Pyrimidine-thiazolidinone derivatives may be used for preventing or treating diseases in humans or animals, and have demonstrated efficacy specifically in treating type-2 diabetes. Methods of synthesizing the pyrimidine-thiazolidinone derivatives, described herein, can provide high yields in a short time and with high purity. The pyrimidine-thiazolidinone derivatives demonstrate improved hypoglycemic activity compared to most anti-diabetic drugs currently available.

  嘧啶噻唑烷酮衍生物可用于预防或治疗人类或动物的疾病，并已证明在治疗2型糖尿病方面具有特效。本文所述的嘧啶噻唑烷酮衍生物合成方法，能在短时间内提供高产率和高纯度。与目前大多数抗糖尿病药物相比，嘧啶噻唑烷酮衍生物显示出更强的降血糖活性。
• Thiazolidine-2,4-dione-linked ciprofloxacin derivatives with broad-spectrum antibacterial, MRSA and topoisomerase inhibitory activities
  作者：Hossameldin A. Aziz、Ahmed M. M. El-Saghier、Mohamed Badr、Gamal El-Din A. Abuo-Rahma、Mai E. Shoman

  DOI：10.1007/s11030-021-10302-7

  日期：2022.6

  3a, 3l and 3m were more potent than ciprofloxacin for topoisomerase IV (IC50 = 0.3–1.9 μM) and gyrase (IC50 = 0.22–0.31 µM) inhibition, which coincide with their antibacterial activity against S. aureus ATCC 6538. Docking against DNA gyrase active site confirmed the ability of the tested compounds to form stable complexes with the enzyme; like that of ciprofloxacin, 3a, 3i, 3k, 3m and 3l reconsidered

  摘要 制备了一系列环丙沙星/噻唑烷-2,4-二酮杂化物3a-m，并通过IR、1 HNMR、13 CNMR和元素分析对其进行了鉴定。设计的杂种的抗菌活性结果显示光谱向革兰氏阳性菌转移。它们对金黄色葡萄球菌 ATCC 6538表现出优异的活性，最有效的化合物是 3a、3e、3g、3i、3k、3l 和 3m，其 MIC 分别为 0.02、2.03、0.64、0.35、1.04、0.22 和 0.36 µM，与其母体化合物环丙沙星（MIC：5.49 µM）相比。他们还表现出对MRSA AUMC 261的有趣活性3a、3e 和 3l 显示 MIC 值为 5 nM。观察到对革兰氏阴性菌的活性降低，化合物 3l 对肺炎克雷伯菌 ATCC10031的活性略高，MIC 值为 0. 08 µM。从机理上讲，将噻唑烷-2,4-二酮环掺入环丙沙星保留了其通过抑制金黄色葡萄球菌的拓扑异构酶IV和DNA旋转酶来抑制DNA合成的能力。化合物
• Tetrabutylammonium bromide and K₂CO₃: an eco-benign catalyst for the synthesis of 5-arylidene-1,3-thiazolidine- 2,4-diones via Knoevenagel condensation
  作者：T. Durai Ananda Kumar、N. Swathi、J. Navatha、C.V.S. Subrahmanyam、K. Satyanarayana

  DOI：10.1080/17415993.2014.970555

  日期：2015.1.2

  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.
• 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 some new 2-amino-6-thiocyanato benzothiazole derivatives bearing 2,4-thiazolidinediones and screening of their in vitro antimicrobial, antitubercular and antiviral activities
  作者：Faiyazalam M. Shaikh、Navin B. Patel、Giuseppina Sanna、Bernardetta Busonera、Paolo La Colla、Dhanji P. Rajani

  DOI：10.1007/s00044-015-1358-0

  日期：2015.8

  A series of new (E)-2-(5-substituted benzylidene-2,4-dioxothiazolidin-3-yl)-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamides have been synthesized. The structures of title compounds have been confirmed by elemental analyses, IR, H-1 NMR and C-13 NMR spectral data. All the synthesized compounds were tested for antimicrobial and antitubercular activity and also were evaluated for anti-HIV activity. Several compounds exhibited good antibacterial activity (9, 15, 27 and 31 against E. coli; 8 and 28 against S. aureus); some displayed good antifungal activity (4, 7, 13, 19, 23, 24, 25 and 31 against C. albicans). Compounds 14, 20 and 22 showed good antitubercular activity. Unfortunately, none of the compounds were found to be active against anti-HIV-1. However, one of the intermediates, the 2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide, showed significant cytotoxicity for MT-4 cells (CC50 = 8.0 A mu M).