(Z)-5-(2,3-dihydroxybenzylidene)-4-thioxo-thiazolidine-2-one | 1365266-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (Z)-5-(2,3-dihydroxybenzylidene)-4-thioxo-thiazolidine-2-one
• 英文别名: (Z)-5-(2,3-dihydroxybenzylidene)-4-thioxothiazolidin-2-one；(5Z)-5-[(2,3-dihydroxyphenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one
• CAS: 1365266-80-3
• 化学式: C₁₀H₇NO₃S₂
• 分子量: 253.302
• InChiKey: HZDSGCIWJYNRPM-DAXSKMNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 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：
  127
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-二羟基苯甲醛 、 4-硫代噻唑烷-2-酮 反应 0.08h， 以80%的产率得到(Z)-5-(2,3-dihydroxybenzylidene)-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

• 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，
• [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。
• 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.