4-(2-amino-4-(4-bromophenyl)-3-cyano-1H-pyrrol-1-yl)benzenesulfonamide | 1616063-59-2

• 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-(2-amino-4-(4-bromophenyl)-3-cyano-1H-pyrrol-1-yl)benzenesulfonamide
• 英文别名: 4-[2-Amino-4-(4-bromophenyl)-3-cyanopyrrol-1-yl]benzenesulfonamide；4-[2-amino-4-(4-bromophenyl)-3-cyanopyrrol-1-yl]benzenesulfonamide
• CAS: 1616063-59-2
• 化学式: C₁₇H₁₃BrN₄O₂S
• 分子量: 417.286
• InChiKey: UZUFADXRFAFRST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-amino-4-(4-bromophenyl)-3-cyano-1H-pyrrol-1-yl)benzenesulfonamide 在 一水合肼 作用下， 以 乙醇 、 苯 为溶剂， 反应 15.0h， 生成 Ethyl 12-(4-bromophenyl)-4-oxo-10-(4-sulfamoylphenyl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,7,11-tetraene-5-carboxylate
  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
• 作为产物：
  描述：

  磺胺 在 sodium ethanolate 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 4-(2-amino-4-(4-bromophenyl)-3-cyano-1H-pyrrol-1-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

• Novel sulfonamides bearing pyrrole and pyrrolopyrimidine moieties as carbonic anhydrase inhibitors: Synthesis, cytotoxic activity and molecular modeling
  作者：Mostafa M. Ghorab、Mariangela Ceruso、Mansour S. Alsaid、Yassin M. Nissan、Reem K. Arafa、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2014.09.059

  日期：2014.11

  Novel pyrrole and pyrrolopyrimidine scaffold-based sulfonamides were designed and synthesized. The carbonic anhydrase (CA) inhibition ability of all derivatives was assessed against the human (h) cytosolic isoforms hCA I and II and the transmembrane, tumor-associated isoforms hCA IX and XII. Some of these sulfonamides were 6-8 fold more potent than the reference drug acetazolamide (AZA, K-i = 5.7 nM)) against hCA XII showing subnanomolar activity. The in vitro cytotoxicity of these derivatives was evaluated against MCF-7, where some derivatives were more cytotoxic than doxorubicin (IC50 = 8.02 mu M) displaying IC50 values between 6.46 and 7.56 mu M. Docking of these sulfonamides with CA XII was performed and their binding modes were comparable with that of AZA. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Ghorab, Mostafa M.; Alsaid, Mansour S.; Nissan, Yassin M., Acta poloniae pharmaceutica, 2014, vol. 71, # 4, p. 603 - 614
  作者：Ghorab, Mostafa M.、Alsaid, Mansour S.、Nissan, Yassin M.

  DOI：——

  日期：——
• 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.
• Ghorab, Mostafa M.; Alsaisd, Mansour S.; Nissan, Yassin M., Acta poloniae pharmaceutica, 2015, vol. 72, # 1, p. 65 - 78
  作者：Ghorab, Mostafa M.、Alsaisd, Mansour S.、Nissan, Yassin M.

  DOI：——

  日期：——