(Z)-5-(4-bromobenzylidene)-4-thioxothiazolidin-2-one | 197515-11-0

• 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: (Z)-5-(4-bromobenzylidene)-4-thioxothiazolidin-2-one
• 英文别名: 5-(4-bromobenzylidene)-4-thioxo-thiazolidin-2-one；(5Z)-5-[(4-bromophenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one
• CAS: 197515-11-0
• 化学式: C₁₀H₆BrNOS₂
• 分子量: 300.2
• InChiKey: NXUMSCUKUIKFSC-YVMONPNESA-N

物化性质

• 熔点：
  188-189 °C
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  86.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-5-(4-bromobenzylidene)-4-thioxothiazolidin-2-one 、 靛红 、 噻莫西酸 以 乙醇 为溶剂， 反应 5.0h， 以91%的产率得到
  参考文献：
  名称：

  通过1,3-偶极环加成反应轻松，高效地超声辅助合成新型双螺杂环化合物。

  摘要：

  已经开发了一种在超声波条件下无需任何催化剂即可合成新型二螺氧杂环吲哚环[吡咯并[1,2-c]噻唑-6,5'-噻唑烷]衍生物的简便高效的一锅三组分方法。结合声化学的优点，如反应条件温和，收率高，反应时间短，我们已经通过偶氮甲亚胺的1，3-偶极环加成反应制备新型二异杂环化合物。特别进行了一些实验来研究超声对环加成反应的加速机理。

  DOI：

  10.1016/j.ultsonch.2011.07.006
• 作为产物：
  描述：

  对溴苯甲醛 、 4-硫代噻唑烷-2-酮 在 sodium acetate 、 溶剂黄146 作用下， 以22%的产率得到(Z)-5-(4-bromobenzylidene)-4-thioxothiazolidin-2-one
  参考文献：
  名称：

  Synthesis, antimicrobial and cytotoxic activities of some 5-arylidene-4-thioxo-thiazolidine-2-ones

  摘要：

  Several 5-arylidene-4-thioxo-thiazolidine-2-ones (3a-n) were synthesized and evaluated as antimicrobial agents against representative strains, including multidrug-resistant strains of clinical isolates. Also, the antiproliferative activity was evaluated against two human carcinoma cell lines (NCI-H292 and HEp-2). The compounds containing the 5-arylidene subunit presented greater antimicrobial activities against Gram positive bacteria, including the multidrug-resistant clinical isolates, than the 4-thioxo-thiazolidine-2-one. Important SAR information was also gathered, such as the contribution of thiocarbonyl attached at 4-position on the thiazolidine heterocyclic for antimicrobial properties. None of the derivatives exhibited significant anti proliferative activity against the human carcinoma cell lines. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.10.006

文献信息

• 5-Arylidenethioxothiazolidinones as Inhibitors of Tyrosyl–DNA Phosphodiesterase I
  作者：Venkata Ramana Sirivolu、Sanjeev Kumar V. Vernekar、Christophe Marchand、Alena Naumova、Adel Chergui、Amelie Renaud、Andrew G. Stephen、Feng Chen、Yuk Y. Sham、Yves Pommier、Zhengqiang Wang

  DOI：10.1021/jm3008773

  日期：2012.10.25

  Tyrosyl-DNA phosphodiesterase I (Tdp1) is a cellular enzyme that repairs the irreversible topoisomerase I (Top1)-DNA complexes and confers chemotherapeutic resistance to Top1 inhibitors. Inhibiting Tdp1 provides an attractive approach to potentiating clinically used Top1 inhibitors. However, despite recent efforts in studying Tdp1 as a therapeutic target, its inhibition remains poorly understood and largely underexplored. We describe herein the discovery of arylidene thioxothiazolidinone as a scaffold for potent Tdp1 inhibitors based on an initial tyrphostin lead compound 8. Through structure-activity relationship (SAR) studies we demonstrated that arylidene thioxothiazolidinones inhibit Tdp1 and identified compound 50 as a submicromolar inhibitor of Tdp1 (IC50 = 0.87 mu M). Molecular modeling provided insight into key interactions essential for observed activities. Some derivatives were also active against endogenous Tdp1 in whole cell extracts. These findings contribute to advancing the understanding on Tdp1 inhibition.
• VYUNOV K. A.; GINAK A. I.; SOCHILIN E. G., ZH. ORGAN. XIMII, 1979, 15, HO 6, 1302-1305
  作者：VYUNOV K. A.、 GINAK A. I.、 SOCHILIN E. G.

  DOI：——

  日期：——