N-(4,6-dimethylpyrimidin-2-yl)-4-((4-oxo-4,5-dihydrothiazol-2-yl)amino)benzenesulfonamide

• 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: N-(4,6-dimethylpyrimidin-2-yl)-4-((4-oxo-4,5-dihydrothiazol-2-yl)amino)benzenesulfonamide
• 英文别名: N-(4,6-dimethylpyrimidin-2-yl)-4-{[(2Z)-4-oxo-1,3-thiazolidin-2-ylidene]amino}benzenesulfonamide；N-(4,6-dimethylpyrimidin-2-yl)-4-[(4-oxo-1,3-thiazolidin-2-ylidene)amino]benzenesulfonamide
• 化学式: C₁₅H₁₅N₅O₃S₂
• 分子量: 377.448
• InChiKey: XWIWLEXBOPAVKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(4,6-dimethylpyrimidin-2-yl)-4-((4-oxo-4,5-dihydrothiazol-2-yl)amino)benzenesulfonamide 、 色酮-3-甲醛 在 sodium acetate 、 溶剂黄146 作用下， 反应 12.0h， 以69%的产率得到N-(4,6-dimethylpyrimidin-2-yl)-4-((4-oxo-5-((4-oxo-4H-chromen-3-yl)methylene)-4,5-dihydrothiazol-2-yl)amino)benzene sulfonamide
  参考文献：
  名称：

  Synthesis, carbonic anhydrase inhibition and cytotoxic activity of novel chromone-based sulfonamide derivatives

  摘要：

  Four series of sulfonamides incorporating chromone moieties were synthesized and assessed for their cytotoxic activity against MCF-7 and A-549 cell lines, considering the fact that some of these tumors overexpress isoforms of carbonic anhydrase (CA, EC 4.2.1.1) which is inhibited by sulfonamides. Most new sulfonamides showed weak inhibitory activity against the offtarget, cytosolic isoforms hCA I, II but effectively inhibited the tumor-associated hCA IX and XII. The most active compounds featured a primary SO2NH2 group and were active in the low micromolar range against MCF-7 and A-549 cell lines. Compound 4a showed IC50 of 0.72 and 0.50 mu M against MCF-7 and A-549 cell lines, respectively, and was further evaluated for its proapoptotic activity which proved enhanced in both tumor types. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.033
• 作为产物：
  描述：

  磺胺二甲嘧啶 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 N-(4,6-dimethylpyrimidin-2-yl)-4-((4-oxo-4,5-dihydrothiazol-2-yl)amino)benzenesulfonamide
  参考文献：
  名称：

  Synthesis, carbonic anhydrase inhibition and cytotoxic activity of novel chromone-based sulfonamide derivatives

  摘要：

  Four series of sulfonamides incorporating chromone moieties were synthesized and assessed for their cytotoxic activity against MCF-7 and A-549 cell lines, considering the fact that some of these tumors overexpress isoforms of carbonic anhydrase (CA, EC 4.2.1.1) which is inhibited by sulfonamides. Most new sulfonamides showed weak inhibitory activity against the offtarget, cytosolic isoforms hCA I, II but effectively inhibited the tumor-associated hCA IX and XII. The most active compounds featured a primary SO2NH2 group and were active in the low micromolar range against MCF-7 and A-549 cell lines. Compound 4a showed IC50 of 0.72 and 0.50 mu M against MCF-7 and A-549 cell lines, respectively, and was further evaluated for its proapoptotic activity which proved enhanced in both tumor types. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.033