4-(9-(4-cyanophenyl)-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)-N-(4-sulfamoylphenyl)benzamide | 1452583-39-9

• 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-(4-cyanophenyl)-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)-N-(4-sulfamoylphenyl)benzamide
• 英文别名: 4-[9-(4-cyanophenyl)-1,8-dioxo-3,4,5,6,7,9-hexahydro-2H-acridin-10-yl]-N-(4-sulfamoylphenyl)benzamide
• CAS: 1452583-39-9
• 化学式: C₃₃H₂₈N₄O₅S
• 分子量: 592.675
• InChiKey: DVBNCGXMQBQXEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  43
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-(4-(氨基磺酰基)苯基)-4-硝基苯甲酰胺 在 sodiumsulfide nonahydrate 、 4-十二烷基苯磺酸 、 sulfur 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 4-(9-(4-cyanophenyl)-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)-N-(4-sulfamoylphenyl)benzamide
  参考文献：
  名称：

  Synthesis of novel acridine and bis acridine sulfonamides with effective inhibitory activity against the cytosolic carbonic anhydrase isoforms II and VII

  摘要：

  4-Amino-N-(4-sulfamoylphenyl)benzamide was synthesized by reduction of 4-nitro-N-(4-sulfamoylphenyl)benzamide and used to synthesize novel acridine sulfonamide compounds, by a coupling reaction with cyclic-1,3-diketones and aromatic aldehydes. The new compounds were investigated as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1), and more precisely the cytosolic isoforms hCA I, II and VII. hCA I was inhibited in the micromolar range by the new compounds (K(i)s of 0.16-9.64 mu M) whereas hCA II and VII showed higher affinity for these compounds, with K(i)s in the range of 15-96 nM for hCA II, and of 4-498 nM for hCA VII. The structure-activity relationships for the inhibition of these isoforms with the acridine-sulfonamides reported here were also elucidated. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.014

文献信息

• Synthesis of novel acridine and bis acridine sulfonamides with effective inhibitory activity against the cytosolic carbonic anhydrase isoforms II and VII
  作者：Ramazan Ulus、İbrahim Yeşildağ、Muhammet Tanç、Metin Bülbül、Muharrem Kaya、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2013.07.014

  日期：2013.9

  4-Amino-N-(4-sulfamoylphenyl)benzamide was synthesized by reduction of 4-nitro-N-(4-sulfamoylphenyl)benzamide and used to synthesize novel acridine sulfonamide compounds, by a coupling reaction with cyclic-1,3-diketones and aromatic aldehydes. The new compounds were investigated as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1), and more precisely the cytosolic isoforms hCA I, II and VII. hCA I was inhibited in the micromolar range by the new compounds (K(i)s of 0.16-9.64 mu M) whereas hCA II and VII showed higher affinity for these compounds, with K(i)s in the range of 15-96 nM for hCA II, and of 4-498 nM for hCA VII. The structure-activity relationships for the inhibition of these isoforms with the acridine-sulfonamides reported here were also elucidated. (C) 2013 Elsevier Ltd. All rights reserved.