(Z)-5-(4-methylbenzylidene)-4-thioxo-thiazolidine-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-methylbenzylidene)-4-thioxo-thiazolidine-2-one
• 英文别名: (5Z)-5-[(4-methylphenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one
• 化学式: C₁₁H₉NOS₂
• 分子量: 235.331
• InChiKey: HINACWNSVOMORM-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  降冰片烯 、 (Z)-5-(4-methylbenzylidene)-4-thioxo-thiazolidine-2-one 在 溶剂黄146 、 对苯二酚 作用下， 反应 1.0h， 以73%的产率得到9-(4-methylphenyl)-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：

  对甲基苯甲醛 、 4-硫代噻唑烷-2-酮 反应 0.08h， 以83%的产率得到(Z)-5-(4-methylbenzylidene)-4-thioxo-thiazolidine-2-one
  参考文献：
  名称：

  微波辅助合成的一些4-硫代-噻唑烷-2-一衍生物

  摘要：

  使用微波辐射技术合成了一系列的（Z）-5-亚芳基-4-硫代-噻唑烷-2-酮（4a-o）。通过IR，1 H NMR，13 C NMR光谱研究和元素分析证实了新合成的化合物的结构。评价所有化合物的初步体外抗微生物和细胞毒性活性。抗菌活性的研究表明，与标准品相比，化合物4d，4f，4g和4h对金黄色葡萄球菌和粪肠球菌具有明显的活性，而化合物4d和4h对白色念珠菌，黄曲霉具有良好的抗真菌活性。 ，A。niger和C. neoformans。在初步的MTT细胞毒性研究中，发现（Z）-5-亚芳基-4-硫代-噻唑烷-2-一衍生物（4k，4l和4m）最有效。化合物4m抑制HeLa，HT29，

  DOI：

  10.2174/157018011796235275

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。
• Microwave-Assisted Synthesis, Antimicrobial and Cytotoxic Activities of Some 4-Thioxo-Thiazolidine-2-One Derivatives
  作者：Shankar G. Alegaon、Kallanagouda R. Alagawadi

  DOI：10.2174/157018011796235275

  日期：2011.8.1

  compounds were evaluated for their preliminary in vitro antimicrobial and cytotoxic activities. The investigation of antimicrobial activity profile revealed that compounds 4d, 4f, 4g, and 4h exhibited marked activity against S. aureus and E. faecalis as compared with the standard while compounds 4d and 4h exhibited good antifungal activities against C. albicans, A. flavus, A. niger and C. neoformans

  使用微波辐射技术合成了一系列的（Z）-5-亚芳基-4-硫代-噻唑烷-2-酮（4a-o）。通过IR，1 H NMR，13 C NMR光谱研究和元素分析证实了新合成的化合物的结构。评价所有化合物的初步体外抗微生物和细胞毒性活性。抗菌活性的研究表明，与标准品相比，化合物4d，4f，4g和4h对金黄色葡萄球菌和粪肠球菌具有明显的活性，而化合物4d和4h对白色念珠菌，黄曲霉具有良好的抗真菌活性。 ，A。niger和C. neoformans。在初步的MTT细胞毒性研究中，发现（Z）-5-亚芳基-4-硫代-噻唑烷-2-一衍生物（4k，4l和4m）最有效。化合物4m抑制HeLa，HT29，
• 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.