1-(4-aminophenyl)-4-benzoyl-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide | 1161947-50-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-aminophenyl)-4-benzoyl-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide
• 英文别名: 1-(4-aminophenyl)-4-benzoyl-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazole-2-yl)-1H-pyrazole-3-carboxamide；1-(4-aminophenyl)-4-benzoyl-5-phenyl-N-(5-sulphamoyl-1,3,4-thiadiazole-2-yl)-1H-pyrazole-3-carboxamide；1-(4-aminophenyl)-4-benzoyl-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)pyrazole-3-carboxamide
• CAS: 1161947-50-7
• 化学式: C₂₅H₁₉N₇O₄S₂
• 分子量: 545.602
• InChiKey: RGCGLSPRERTEBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  213
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(4-aminophenyl)-4-benzoyl-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide 在 盐酸 、 sodium acetate 、 potassium iodide 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 4-benzoyl-1-(4-iodophenyl)-5-phenyl-N-(5-sulphamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  Synthesis and antiproliferative activities of some pyrazole-sulfonamide derivatives

  摘要：

  In this study, a series of pyrazole-sulfonamide derivatives were designed and synthesized from 1-(4-aminophenyl)-4-benzoyl-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide (1). The newly synthesized sulfonamides were characterized by FT-IR, H-1 NMR, C-13 NMR, and elemental analyses. The compounds were tested for their in vitro antiproliferative activities against HeLa and C6 cell lines. The tests were carried out as dose-dependent assay starting from 5 to 100 mu g/mL. All compounds showed especially cell selective effect against rat brain tumor cells (C6). Some of the tested compounds (3) and (7) showed promising broad spectrum antitumor activity comparable to the activities of the commonly used anticancer drugs, 5-fluorouracil and cisplatin.

  DOI：

  10.1007/s00044-013-0721-2
• 作为产物：
  描述：

  4-benzoyl-1-(4-nitrophenyl)-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide 在 盐酸 、 sodiumsulfide nonahydrate 作用下， 以 水 为溶剂， 生成 1-(4-aminophenyl)-4-benzoyl-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  Synthesis of 5-amino-1,3,4-thiadiazole-2-sulphonamide derivatives and their inhibition effects on human carbonic anhydrase isozymes

  摘要：

  In this study, some novel inhibitors were synthesised from the further stage reactions of 4-benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carbonyl chloride with 5-amino-1,3,4-thiadiazole-2-sulphonamide 1 (inhibitor 1). They were characterised by elemental and spectral (

  DOI：

  10.3109/14756366.2010.491795

文献信息

• Effects of new 5-amino-1,3,4-thiadiazole-2-sulfonamide derivatives on human carbonic anhydrase isozymes
  作者：Rahmi Kasımoğulları、Metin Bülbül、Hatice Günhan、Hülya Güleryüz

  DOI：10.1016/j.bmc.2009.03.048

  日期：2009.5

  Pyrazole carboxylic acid amides of 5-amino-1,3,4-thiadiazole-2-sulfonamide 1 (inhibitor 1) were synthesized from 4-benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carbonyl chloride and 4-benzoyl-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carbonyl chloride compounds. Human carbonic anhydrase isoenzymes (hCA-I and hCA-II) were purified from erythrocyte cells by the affinity chromatography. The inhibitory effects of inhibitor 1, acetazolamide (AAZ), and of 16 newly synthesized amides (8-11, 12a-f, 13a-c, 14a-b, and 15) on hydratase and esterase activities of these isoenzymes have been studied in vitro. The average IC50 values of the new compounds (8-11,12a-f, 13a-c, 14a-b, and 15) for hydratase activity ranged from 3.25 to 4.75 mu M for hCA-I and from 0.055 to 2.6 mu M for hCA-II. The mean IC50 values of the same inhibitors for esterase activity were in the range of 2.7-6.6 mu M for hCA-I ( with the exception of inhibitor 10, which did not inhibit the esterase activity of hCA-I) and of 0.013-4.2 mu M for hCA-II. The K-i values for new compounds (8-11, 12a-f, 13a-c, 14a-b, and 15) were observed well below that of the parent compound inhibitor 1 and were also comparable to that of AAZ under the same experimental conditions. The comparison of newly synthesized amides to inhibitor 1 and to AAZ indicated that the new derivatives preferentially inhibit hCA-II and are more potent inhibitors of hCA-II than the parent inhibitor 1 and AAZ. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of 5-amino-1,3,4-thiadiazole-2-sulphonamide derivatives and their inhibition effects on human carbonic anhydrase isozymes
  作者：Rahmi Kasımoğulları、Metin Bülbül、Samet Mert、Hülya Güleryüz

  DOI：10.3109/14756366.2010.491795

  日期：2011.4.1

  In this study, some novel inhibitors were synthesised from the further stage reactions of 4-benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carbonyl chloride with 5-amino-1,3,4-thiadiazole-2-sulphonamide 1 (inhibitor 1). They were characterised by elemental and spectral (
• Synthesis and antiproliferative activities of some pyrazole-sulfonamide derivatives
  作者：Samet Mert、Ayşe Şahin Yağlıoğlu、Ibrahim Demirtas、Rahmi Kasımoğulları

  DOI：10.1007/s00044-013-0721-2

  日期：2014.3

  In this study, a series of pyrazole-sulfonamide derivatives were designed and synthesized from 1-(4-aminophenyl)-4-benzoyl-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide (1). The newly synthesized sulfonamides were characterized by FT-IR, H-1 NMR, C-13 NMR, and elemental analyses. The compounds were tested for their in vitro antiproliferative activities against HeLa and C6 cell lines. The tests were carried out as dose-dependent assay starting from 5 to 100 mu g/mL. All compounds showed especially cell selective effect against rat brain tumor cells (C6). Some of the tested compounds (3) and (7) showed promising broad spectrum antitumor activity comparable to the activities of the commonly used anticancer drugs, 5-fluorouracil and cisplatin.