4-(9-(4-bromophenyl)-7H-pyrrolo[3,2-e][1,2,3,4]tetrazolo[1,5-c]pyrimidin-7-yl)benzenesulfonamide | 1616063-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-(9-(4-bromophenyl)-7H-pyrrolo[3,2-e][1,2,3,4]tetrazolo[1,5-c]pyrimidin-7-yl)benzenesulfonamide
• 英文别名: 4-[12-(4-Bromophenyl)-3,4,5,6,8,10-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]benzenesulfonamide；4-[12-(4-bromophenyl)-3,4,5,6,8,10-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]benzenesulfonamide
• CAS: 1616063-69-4
• 化学式: C₁₈H₁₂BrN₇O₂S
• 分子量: 470.309
• InChiKey: YWRVKUQSWBCUCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(3-amino-5-(4-bromophenyl)-4-imino-3,4-dihydropyrrolo[2,3-d]pyrimidin-7-yl)benzenesulfonamide 在 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 3.0h， 以78%的产率得到4-(9-(4-bromophenyl)-7H-pyrrolo[3,2-e][1,2,3,4]tetrazolo[1,5-c]pyrimidin-7-yl)benzenesulfonamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors: Synthesis, molecular docking, cytotoxic and inhibition of the human carbonic anhydrase isoforms I, II, IX, XII with novel benzenesulfonamides incorporating pyrrole, pyrrolopyrimidine and fused pyrrolopyrimidine moieties

  摘要：

  A series of novel pyrroles, pyrrolopyrimidines, pyrazolopyrrolopyrimidine, triazolopyrrolopyrimidines, tetrazolopyrrolopyrimidine, triazinopyrrolopyrimidines and pyrrolopyrimidotriazepines bearing the biologically active benzenesulfonamide moiety were synthesized by using pyrrole-o-amino-carbonitrile as key intermediate. All the synthesized compounds were evaluated for their in vitro carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects against the human (h) isoforms hCA I, II, IX and XII. Among the tested derivatives, compounds 16, 18 and 20-24 showed potent activity as inhibitors for the tumor associated transmembrane isoforms (hCA IX and XII) in the nanomolar and subnanomolar range, with high selectivity. All compounds underwent cytotoxic activity assays on human breast cancer cell line (MCF-7) showing effective activity, comparable to that of the clinically used drug doxorubicin.

  DOI：

  10.1016/j.bmc.2014.05.009

文献信息

• Carbonic anhydrase inhibitors: Synthesis, molecular docking, cytotoxic and inhibition of the human carbonic anhydrase isoforms I, II, IX, XII with novel benzenesulfonamides incorporating pyrrole, pyrrolopyrimidine and fused pyrrolopyrimidine moieties
  作者：Mostafa M. Ghorab、Mansour S. Alsaid、Mariangela Ceruso、Yassin M. Nissan、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2014.05.009

  日期：2014.7

  A series of novel pyrroles, pyrrolopyrimidines, pyrazolopyrrolopyrimidine, triazolopyrrolopyrimidines, tetrazolopyrrolopyrimidine, triazinopyrrolopyrimidines and pyrrolopyrimidotriazepines bearing the biologically active benzenesulfonamide moiety were synthesized by using pyrrole-o-amino-carbonitrile as key intermediate. All the synthesized compounds were evaluated for their in vitro carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects against the human (h) isoforms hCA I, II, IX and XII. Among the tested derivatives, compounds 16, 18 and 20-24 showed potent activity as inhibitors for the tumor associated transmembrane isoforms (hCA IX and XII) in the nanomolar and subnanomolar range, with high selectivity. All compounds underwent cytotoxic activity assays on human breast cancer cell line (MCF-7) showing effective activity, comparable to that of the clinically used drug doxorubicin.