4-(2-(2-chlorophenyl)-4-oxothiazolidin-3-yl)benzenesulfonamide | 1334224-49-5

• 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: 4-(2-(2-chlorophenyl)-4-oxothiazolidin-3-yl)benzenesulfonamide
• 英文别名: 2-(2-chlorophenyl)-3-(4-sulphonamidophenyl)thiazolidin-4-one；4-[2-(2-Chlorophenyl)-4-oxo-thiazolidin-3-yl]benzenesulfonamide；4-[2-(2-chlorophenyl)-4-oxo-1,3-thiazolidin-3-yl]benzenesulfonamide
• CAS: 1334224-49-5
• 化学式: C₁₅H₁₃ClN₂O₃S₂
• 分子量: 368.865
• InChiKey: ZFAQTOYSVLYBOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯苯甲醛 、 磺胺 生成 4-(2-(2-chlorophenyl)-4-oxothiazolidin-3-yl)benzenesulfonamide
  参考文献：
  名称：

  噻唑烷酮衍生物作为抗微生物和抗病毒药物的设计，合成和评估

  摘要：

  通过各自的芳香胺，芳香醛和巯基乙酸在干苯/甲苯中的反应，制备了一系列1,3-噻唑烷-4-酮衍生物。根据元素分析，IR，1 HNMR和质谱对新合成的化合物进行表征。对新合成的最终化合物进行了体外评估抗菌，抗真菌和抗病毒活性。初步结果表明，与标准药物环丙沙星和氟康唑相比，某些化合物的抗菌活性范围为7–13μg/ mL，抗真菌活性范围为13–17μg/ mL。结构与活性之间的关系研究表明，噻唑烷酮核的2和3位上的取代基的性质对这类药物的体外抗菌和抗病毒活性具有重大影响。

  DOI：

  10.1111/j.1747-0285.2011.01149.x

文献信息

• Design and synthesis of novel 4-(4-oxo-2-arylthiazolidin-3-yl)benzenesulfonamides as selective inhibitors of carbonic anhydrase IX over I and II with potential anticancer activity
  作者：Sharad Kumar Suthar、Sumit Bansal、Sandeep Lohan、Vikarm Modak、Anil Chaudhary、Amit Tiwari

  DOI：10.1016/j.ejmech.2013.06.003

  日期：2013.8

  The novel 4-(4-oxo-2-arylthiazolidin-3-yl)benzenesulfonamide derivatives were designed and synthesized for selective carbonic anhydrase IX (CA IX) inhibitory activity with anticancer potential. In the CA inhibition assay, 3f was found to be the most potent and selective inhibitor of CA IX with inhibitory constant (K-I) value of 2.2 nM. Among the synthesized compounds, 3f showed IC50 values of 5.03 mu g/ml (cisplatin: 6.56 mu g/ml), 5.81 mu g/ml (cisplatin: 5.85 mu g/ml), and 23.93 mu g/ml (cisplatin: 2.75 mu g/ml) against COLO-205, MDA-MB-231, and DU-145 cell lines, respectively. At IC50, 3f caused cell shrinkage, nuclear condensation, and nuclear fragmentation events characteristic to apoptosis in the Hoechst 33258 and acridine orange-ethidium bromide staining studies of COLO-205 cells. In the Dalton's lymphoma ascites (DLA) solid tumor model 3f decreased tumor volume by 64.83% (cisplatin: 71.62%), while increase in mean body weight was found to be only 4.09% (cisplatin: 3.47%). (C) 2013 Elsevier Masson SAS. All rights reserved.
• Design, Synthesis, and Evaluation of Thiazolidinone Derivatives as Antimicrobial and Anti-viral Agents
  作者：Veerasamy Ravichandran、Abhishek Jain、Krishnan S. Kumar、Harish Rajak、Ram K. Agrawal

  DOI：10.1111/j.1747-0285.2011.01149.x

  日期：2011.9

  acid in dry benzene/toluene. The newly synthesized compounds were characterized on the basis of elemental analysis, IR, 1HNMR, and mass spectra. The newly synthesized final compounds were evaluated for their in vitro antibacterial, antifungal, and anti‐viral activities. Preliminary results indicated that some of the compounds demonstrated antibacterial activity in the range of 7–13 μg/mL, antifungal

  通过各自的芳香胺，芳香醛和巯基乙酸在干苯/甲苯中的反应，制备了一系列1,3-噻唑烷-4-酮衍生物。根据元素分析，IR，1 HNMR和质谱对新合成的化合物进行表征。对新合成的最终化合物进行了体外评估抗菌，抗真菌和抗病毒活性。初步结果表明，与标准药物环丙沙星和氟康唑相比，某些化合物的抗菌活性范围为7–13μg/ mL，抗真菌活性范围为13–17μg/ mL。结构与活性之间的关系研究表明，噻唑烷酮核的2和3位上的取代基的性质对这类药物的体外抗菌和抗病毒活性具有重大影响。