(Z)-5-(4-fluorobenzylidene)-4-thioxothiazolidin-2-one

• 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-fluorobenzylidene)-4-thioxothiazolidin-2-one
• 英文别名: (5Z)-5-[(4-fluorophenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one
• 化学式: C₁₀H₆FNOS₂
• 分子量: 239.294
• InChiKey: RZKSTKVXQLZHTI-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  4

反应信息

• 作为反应物：
  描述：

  降冰片烯 、 (Z)-5-(4-fluorobenzylidene)-4-thioxothiazolidin-2-one 在 溶剂黄146 、 对苯二酚 作用下， 反应 1.0h， 以79%的产率得到9-(4-fluorophenyl)-3,7-dithia-5-azatetracyclo[9.2.1.0^2,10.0^4,8]tetradec-4(8)-en-6-one
  参考文献：
  名称：

  Anticancer thiopyrano[2,3-d][1,3]thiazol-2-ones with norbornane moiety. Synthesis, cytotoxicity, physico-chemical properties, and computational studies

  摘要：

  A series of novel 9-substituted-3,7-dithia-5-azatetracyclo[9.2.1.0(2,10).O-4,O-8]tetradecen-4(8)-ones-6 have been synthesized by a stereoselective hetero-Diels-Alder reaction of 5-ylidene-4-thioxo-2-thiazolidone derivatives with norbornene-2. All the compounds have been evaluated for antitumor activity in in vitro human tumor cell lines, and 10 of them possessed significant and selective cytotoxicity (MGM logGI(50) similar to -4.17 to -4.98, for individual cell lines logGI(50) up to -8). COMPARE analyses of differential growth inhibition patterns of compounds at the GI(50) level showed high correlations with some of the antitubulin agents. The lipophilicity of the compounds was studied by RP-TLC and found to correlate well with calculated log P values. Docking and structure-activity relationship studies produced seven QSAR models with 2 or 3 variables, with correlation coefficients r(2) > 0.9 and leave-one-out cross-validation correlation coefficients, q(2) > 0.8. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.053
• 作为产物：
  描述：

  对氟苯甲醛 、 4-硫代噻唑烷-2-酮 在 sodium acetate 、 溶剂黄146 作用下， 以18%的产率得到(Z)-5-(4-fluorobenzylidene)-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

• A facile and efficient ultrasound-assisted synthesis of novel dispiroheterocycles through 1,3-dipolar cycloaddition reactions
  作者：Yu Hu、Yi Zou、Hui Wu、Daqing Shi

  DOI：10.1016/j.ultsonch.2011.07.006

  日期：2012.3

  for synthesis of novel dispirooxindolecyclo[pyrrolo[1,2-c]thiazole-6,5'-thiazolidine] derivatives without any catalysts under ultrasonic condition has been developed. Combining with the advantages of sonochemistry, such as mild reaction conditions, good yield and short reaction times, we have made a progress on construction of novel disiproheterocyclic compounds via the 1,3-dipolar cycloaddition of

  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。
• [EN] THIOXOTHIAZOLIDINONE DERIVATIVES USEFUL AS INHIBITORS OF TDP1<br/>[FR] DÉRIVÉS DE THIOXOTHIAZOLIDINONES UTILES EN TANT QU'INHIBITEURS DE TDP1
  申请人：US HEALTH

  公开号：WO2013055771A1

  公开（公告）日：2013-04-18

  Tdp1 inhibitors of Formula (I) and methods of using those inhibitors to treat cancer are provided in this disclosure. R1 is hydrogen or lower alkyl and G is a substituted phenyl or optionally substituted heteroaryl group. The disclosed Tdp1 inhibitors may be used alone to treat cancer, but may also be used in combination with another active agent, such as camptothecin or a camptothecin analogue.

  本公开提供的是公式（I）的Tdp1抑制剂及其用于治疗癌症的方法。其中，R1为氢或低碳基，G为取代苯基或可选取代的杂环芳基基团。所披露的Tdp1抑制剂可单独用于治疗癌症，也可与另一种活性剂（例如喜树碱或喜树碱类似物）联合使用。
• Synthesis, antimicrobial and cytotoxic activities of some 5-arylidene-4-thioxo-thiazolidine-2-ones
  作者：Frederico L. Gouveia、Renata M.B. de Oliveira、Tatiane B. de Oliveira、Ivanildo M. da Silva、Silene C. do Nascimento、Kêsia X.F.R. de Sena、Julianna F.C. de Albuquerque

  DOI：10.1016/j.ejmech.2008.10.006

  日期：2009.5

  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.
• 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.
• Anticancer thiopyrano[2,3-d][1,3]thiazol-2-ones with norbornane moiety. Synthesis, cytotoxicity, physico-chemical properties, and computational studies
  作者：Roman Lesyk、Borys Zimenkovsky、Dmytro Atamanyuk、Frank Jensen、Katarzyna Kieć-Kononowicz、Andrzej Gzella

  DOI：10.1016/j.bmc.2006.03.053

  日期：2006.8

  A series of novel 9-substituted-3,7-dithia-5-azatetracyclo[9.2.1.0(2,10).O-4,O-8]tetradecen-4(8)-ones-6 have been synthesized by a stereoselective hetero-Diels-Alder reaction of 5-ylidene-4-thioxo-2-thiazolidone derivatives with norbornene-2. All the compounds have been evaluated for antitumor activity in in vitro human tumor cell lines, and 10 of them possessed significant and selective cytotoxicity (MGM logGI(50) similar to -4.17 to -4.98, for individual cell lines logGI(50) up to -8). COMPARE analyses of differential growth inhibition patterns of compounds at the GI(50) level showed high correlations with some of the antitubulin agents. The lipophilicity of the compounds was studied by RP-TLC and found to correlate well with calculated log P values. Docking and structure-activity relationship studies produced seven QSAR models with 2 or 3 variables, with correlation coefficients r(2) > 0.9 and leave-one-out cross-validation correlation coefficients, q(2) > 0.8. (c) 2006 Elsevier Ltd. All rights reserved.