2-(p-bromophenyl)imino-1,3-thiazolidin-4-one | 21262-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(p-bromophenyl)imino-1,3-thiazolidin-4-one
• 英文别名: 2-(p-Bromphenyl)-iminothiazolidin-4-on；2-(4-bromophenylimino)-1,3-thiazolidin-4-one；2-(4-bromo-anilino)-thiazol-4-one；(2Z)-2-[(4-bromophenyl)imino]-1,3-thiazolidin-4-one；2-(4-bromophenyl)imino-1,3-thiazolidin-4-one
• CAS: 21262-25-9
• 化学式: C₉H₇BrN₂OS
• mdl: MFCD02379248
• 分子量: 271.137
• InChiKey: XWVRIDYDLXXVNL-UHFFFAOYSA-N

物化性质

• 熔点：
  229-230 °C
• 沸点：
  367.3±44.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(p-bromophenyl)imino-1,3-thiazolidin-4-one 在 四丁基溴化铵 、 2,3-二甲基苯胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以42%的产率得到(4-chlorothiazol-2-yl)-4-bromophenylamine
  参考文献：
  名称：

  [4-(Imidazol-1-yl)thiazol-2-yl]phenylamines. A Novel Class of Highly Potent Colchicine Site Binding Tubulin Inhibitors: Synthesis and Cytotoxic Activity on Selected Human Cancer Cell Lines

  摘要：

  Synthesis and cytotoxic activity in the submicromolar range of a series of [4-(imidazol-l-yl)thiazol-2-yl]-phenylamines are described. Cell cycle dependent cytotoxicity on RKO human colon carcinoma cells with inducible expression of p27(kip1) and the influence on microtubule formation were investigated. Considering the significant correlation between the IC50 values of tubulin polymerization inhibition, [H-3]colchicine competition, and cytotoxicity of the investigated compounds, tubulin is the main cellular target. The inhibition of microtubule formation was shown to be mediated by interference with the colchicine binding site of tubulin. In depth analysis of the investigated compounds allowed the identification of modifications that altered the pharmacological profile of the compounds from a mitosis-inducing phenotype to a G1 cell cycle arresting phenotype.

  DOI：

  10.1021/jm060545p
• 作为产物：
  描述：

  1-benzoyl-3-(4-bromophenyl)thiourea 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-(p-bromophenyl)imino-1,3-thiazolidin-4-one
  参考文献：
  名称：

  [4-(Imidazol-1-yl)thiazol-2-yl]phenylamines. A Novel Class of Highly Potent Colchicine Site Binding Tubulin Inhibitors: Synthesis and Cytotoxic Activity on Selected Human Cancer Cell Lines

  摘要：

  Synthesis and cytotoxic activity in the submicromolar range of a series of [4-(imidazol-l-yl)thiazol-2-yl]-phenylamines are described. Cell cycle dependent cytotoxicity on RKO human colon carcinoma cells with inducible expression of p27(kip1) and the influence on microtubule formation were investigated. Considering the significant correlation between the IC50 values of tubulin polymerization inhibition, [H-3]colchicine competition, and cytotoxicity of the investigated compounds, tubulin is the main cellular target. The inhibition of microtubule formation was shown to be mediated by interference with the colchicine binding site of tubulin. In depth analysis of the investigated compounds allowed the identification of modifications that altered the pharmacological profile of the compounds from a mitosis-inducing phenotype to a G1 cell cycle arresting phenotype.

  DOI：

  10.1021/jm060545p

文献信息

• 一种5-(1H-吲哚-3-亚甲基)-1,3-噻唑烷-4- 酮类衍生物及其合成方法和应用
  申请人：西安交通大学

  公开号：CN104059060B

  公开（公告）日：2017-08-01

  一种5‑(1H‑吲哚‑3‑亚甲基)‑1,3‑噻唑烷‑4‑酮类衍生物及其合成方法和应用，以乙醇和或水为溶剂，将取代2‑取代亚氨基‑1,3‑噻唑烷‑4‑酮与1H‑吲哚‑3‑甲醛在哌啶催化条件下，回流反应，通过分子间脱水缩合反应形成亚甲基连接基，得到5‑(1H‑吲哚‑3‑亚甲基)‑1,3‑噻唑烷‑4‑酮类衍生物。其中所涉及的中间体2‑取代亚氨基噻唑烷‑4‑酮是由各种单取代的硫脲氯乙酸乙酯或氯乙酸在低沸点溶剂中经回流条件下的环合反应制备而得，中间体2‑取代亚氨基‑3‑取代‑1,3,‑噻唑烷‑4‑酮由各种双取代的对称硫脲和氯乙酸通过绿色环保合成工艺制备。对所有目标化合物在酶分子水平上的生物活性初步筛选实验结果显示，目标产物对PTP1B和CDC25B在不同程度上显示一定的抑制活性。
• One-pot strategy for thiazole tethered 7-ethoxy quinoline hybrids: Synthesis and potential antimicrobial agents as dihydrofolate reductase (DHFR) inhibitors with molecular docking study
  作者：Yousry A. Ammar、Sondos M.A. Abd El-Hafez、Sadia A. Hessein、Abeer M. Ali、Ahmed A. Askar、Ahmed Ragab

  DOI：10.1016/j.molstruc.2021.130748

  日期：2021.10

  challenge can be solved by discovering new targets and inhibitors. The current study involved synthesis quinoline based thiazole analogues for quinoline antibiotic class using classic organic synthesis. The designed derivatives were tested against eight standard microbial pathogens. Among them, seven derivatives showed good antimicrobial activity with MIC and MBC values ranged between (0.97-62.5) µg/mL

  在世界各地，尤其是发展中国家，对人类健康的主要威胁之一是由于滥用抗生素而导致的抗生素耐药性。这一挑战可以通过发现新的靶点和抑制剂来解决。目前的研究涉及使用经典有机合成合成喹啉类抗生素的喹啉类噻唑类似物。针对八种标准微生物病原体对设计的衍生物进行了测试。其中，7 种衍生物表现出良好的抗菌活性，MIC 和 MBC 值分别介于 (0.97-62.5) µg/mL 和 (1.94-118.7) µg/mL 之间。另外，活性衍生物显示出对三种MDR细菌染色的良好活性。化合物11b和5a表现出对金黄色葡萄球菌最具活性的衍生物和大肠杆菌，MIC (1.95-7.81) µg/mL 和 MBC (3.31-15.62) µg/mL 其次是其他衍生物，与环丙沙星和万古霉素相比。此外，化合物6、11c和15出现了对 MDR铜绿假单胞菌最具活性的衍生物，其 MIC 和 MBC 值低于 10 µg/mL。这些衍生物被认为通过抑制显示
• Synthesis of some oxa- and thiazolidine-1,3-diones and their oxiranyl and thiiranyl derivatives
  作者：G. V. Babaeva、N. G. Shikhaliev、V. S. Gasanov、K. B. Kurbanov、M. A. Allakhverdiev

  DOI：10.1134/s107042801106025x

  日期：2011.6
• In vitro cytotoxic activity of thiazole-indenoquinoxaline hybrids as apoptotic agents, design, synthesis, physicochemical and pharmacokinetic studies
  作者：Eman A. Fayed、Yousry A. Ammar、Ahmed Ragab、Nirvana A. Gohar、Ahmed B.M. Mehany、Amel M. Farrag

  DOI：10.1016/j.bioorg.2020.103951

  日期：2020.7

  In this study, anti-proliferative effects of twenty-seven indeno[1,2-b]quinoxalin-11-one derivatives were investigated in three human cancer cell lines, namely: the colon cancer cell line HCT-116, the liver cancer cell line HepG-2, and the breast cancer cell line MCF-7. Among them, 5, 6, 13, 14a, b and 15d-f derivatives displayed excellent anti-proliferative activities against the three tested cell lines compared to the reference standard Imatinib. Therefore, they were selected for further studies. First, to ensure the safety of our hits, investigation of the IC50 values on normal human cells (WI-38) was executed indicating that, they are highly selective (IC50 > 107 μM) in their cytotoxic effect. Second, the induction of apoptosis by these active compounds was achieved by down-regulation of Bcl-2 and up-regulation of BAX and caspase-3. Further investigations have shown that 14b and 15f, the most potent derivatives, induced cell cycle arrest at G2/M phase. Moreover, in silico evaluation of ADME properties indicated that all the potent compounds are orally bioavailable with no permeation to the blood brain barrier.
• Ramsh,S.M. et al., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 793 - 796
  作者：Ramsh,S.M. et al.

  DOI：——

  日期：——