4-(2-(3-bromophenyl)-4-oxothiazolidin-3-yl)benzenesulfonamide | 1449244-39-6

• 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-(3-bromophenyl)-4-oxothiazolidin-3-yl)benzenesulfonamide
• 英文别名: 4-[2-(3-Bromophenyl)-4-oxo-1,3-thiazolidin-3-yl]benzenesulfonamide；4-[2-(3-bromophenyl)-4-oxo-1,3-thiazolidin-3-yl]benzenesulfonamide
• CAS: 1449244-39-6
• 化学式: C₁₅H₁₃BrN₂O₃S₂
• 分子量: 413.316
• InChiKey: XBZFCFJWCTVVAN-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：

  间溴苯甲醛 、 巯基乙酸 、 磺胺 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以55%的产率得到4-(2-(3-bromophenyl)-4-oxothiazolidin-3-yl)benzenesulfonamide
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.06.003

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.