4-(9-(3,4-dimethoxyphenyl)-2,2,7,7-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridine-10(9H)-yl)benzenesulfonamide | 1392417-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(9-(3,4-dimethoxyphenyl)-2,2,7,7-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridine-10(9H)-yl)benzenesulfonamide
• 英文别名: 4-(9-(3,4-Dimethoxyphenyl)-2,2,7,7-tetramethyl inverted question mark1,8-dioxo inverted question mark1,2,3,4,5,6,7,8-octahydro acridine inverted question mark10(9H)-yl)benzenesulfonamide (11)；4-[9-(3,4-dimethoxyphenyl)-2,2,7,7-tetramethyl-1,8-dioxo-4,5,6,9-tetrahydro-3H-acridin-10-yl]benzenesulfonamide
• CAS: 1392417-04-7
• 化学式: C₃₁H₃₆N₂O₆S
• 分子量: 564.703
• InChiKey: RVWYHRHTBVXFTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4,4-二甲基-1,3-环己二酮 、 3,4-二甲氧基苯甲醛 、 磺胺 在 4-十二烷基苯磺酸 作用下， 以 水 为溶剂， 反应 10.0h， 以76%的产率得到4-(9-(3,4-dimethoxyphenyl)-2,2,7,7-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridine-10(9H)-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and characterization of novel dioxoacridine sulfonamide derivatives as new carbonic anhydrase inhibitors

  摘要：

  Novel dioxoacridine sulfonamide compounds were synthesized from reaction of cyclic 1,3-diketones, sulfanilamide (4-amino benzene sulfonamide) and aromatic aldehydes. The structures of these compounds were confirmed by using spectral analysis (IR, H-NMR, C-13-NMR, and mass). Human carbonic anhydrase isoenzymes (hCA I and hCA II) were purified from erythrocyte cells by affinity chromatography. The inhibitory effects of sulfanilamide, acetazolamide (AAZ), and newly synthesized sulfonamides on hydratase and esterase activities of these isoenzymes have been studied in vitro. The IC50 values of compounds for esterase activity are 0.71-0.11 mu M for hCA I and 0.45-0.12 mu M for hCA II, respectively. The K-i values of these inhibitors were determined as 0,38-0,008 mu M for hCA I and 0,19-0,001 mu M for hCA II, respectively.

  DOI：

  10.3109/14756366.2011.599029

文献信息

• Synthesis and characterization of novel dioxoacridine sulfonamide derivatives as new carbonic anhydrase inhibitors
  作者：Muharrem Kaya、Erhan Basar、Emrah Çakir、Ekrem Tunca、Metin Bülbül

  DOI：10.3109/14756366.2011.599029

  日期：2012.8.1

  Novel dioxoacridine sulfonamide compounds were synthesized from reaction of cyclic 1,3-diketones, sulfanilamide (4-amino benzene sulfonamide) and aromatic aldehydes. The structures of these compounds were confirmed by using spectral analysis (IR, H-NMR, C-13-NMR, and mass). Human carbonic anhydrase isoenzymes (hCA I and hCA II) were purified from erythrocyte cells by affinity chromatography. The inhibitory effects of sulfanilamide, acetazolamide (AAZ), and newly synthesized sulfonamides on hydratase and esterase activities of these isoenzymes have been studied in vitro. The IC50 values of compounds for esterase activity are 0.71-0.11 mu M for hCA I and 0.45-0.12 mu M for hCA II, respectively. The K-i values of these inhibitors were determined as 0,38-0,008 mu M for hCA I and 0,19-0,001 mu M for hCA II, respectively.