4-(((4-oxo-4H-chromen-3-yl)methyl)amino)-N-(pyrimidin-2-yl)benzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-(((4-oxo-4H-chromen-3-yl)methyl)amino)-N-(pyrimidin-2-yl)benzenesulfonamide
• 英文别名: 4-[(4-oxochromen-3-yl)methylamino]-N-pyrimidin-2-ylbenzenesulfonamide
• 化学式: C₂₀H₁₆N₄O₄S
• 分子量: 408.437
• InChiKey: YGUVHHBDZJDABW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2'-羟基苯乙酮 在 sodium tetrahydroborate 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 27.5h， 生成 4-(((4-oxo-4H-chromen-3-yl)methyl)amino)-N-(pyrimidin-2-yl)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

文献信息

• Synthesis, carbonic anhydrase inhibition and cytotoxic activity of novel chromone-based sulfonamide derivatives
  作者：Fadi M. Awadallah、Tamer A. El-Waei、Mona M. Hanna、Safinaz E. Abbas、Mariangela Ceruso、Beyza Ecem Oz、Ozen Ozensoy Guler、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2015.04.033

  日期：2015.5

  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.