N-(diaminomethylene)-4-[3,3,6,6-tetramethyl-9-[4-(methylthio)phenyl]-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl]benzenesulfonamide | 1555916-73-8

• 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: N-(diaminomethylene)-4-[3,3,6,6-tetramethyl-9-[4-(methylthio)phenyl]-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl]benzenesulfonamide
• 英文别名: 2-[4-[3,3,6,6-tetramethyl-9-(4-methylsulfanylphenyl)-1,8-dioxo-4,5,7,9-tetrahydro-2H-acridin-10-yl]phenyl]sulfonylguanidine
• CAS: 1555916-73-8
• 化学式: C₃₁H₃₆N₄O₄S₂
• 分子量: 592.783
• InChiKey: BROKLWFJLLJXKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  170
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 磺胺脒 、 4-(甲基巯基)苯甲醛 在 硫酸 作用下， 以 水 为溶剂， 反应 48.0h， 以76%的产率得到N-(diaminomethylene)-4-[3,3,6,6-tetramethyl-9-[4-(methylthio)phenyl]-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl]benzenesulfonamide
  参考文献：
  名称：

  Facile, highly efficient, and clean one-pot synthesis of acridine sulfonamide derivatives at room temperature and their inhibition of human carbonic anhydrase isoenzymes

  摘要：

  Reaction of dimedone, 4-amino-N-(diaminomethylene) benzenesulfonamide, and aromatic aldehydes was successfully realized using sulfuric acid as a cheap catalyst. Synthesis of novel acridine sulfonamide compounds was performed providing high yields in water as the solvent at room temperature. This method has several advantages such as use of a green solvent, high yields, and efficient one-pot procedure. In addition, human carbonic anhydrase isoenzymes (hCA I and hCA II) were purified from erythrocyte cells by affinity chromatography. The inhibitory effects of acetazolamide and the newly synthesized acridine sulfonamides on hydratase and esterase activities of these isoenzymes was studied in vitro. The esterase IC50 values of the new compounds are 47.2-230.1 mu M for hCA I and 50.1-275.0 mu M for hCA II.

  DOI：

  10.1007/s00706-013-1145-x