4-[4-(4-methylphenyl)-1-oxophthalazin-2(1H)-yl]-benzenesulfonamide | 847734-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-[4-(4-methylphenyl)-1-oxophthalazin-2(1H)-yl]-benzenesulfonamide
• 英文别名: 4-[4-(4-Methylphenyl)-1-oxophthalazin-2-yl]benzenesulfonamide
• CAS: 847734-10-5
• 化学式: C₂₁H₁₇N₃O₃S
• 分子量: 391.45
• InChiKey: MGVHPGCNIGEQCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  异氰酸丙酯 、 4-[4-(4-methylphenyl)-1-oxophthalazin-2(1H)-yl]-benzenesulfonamide 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and blood glucose lowering activity of some novel benzenesulfonylthiourea derivatives substituted with 4-aryl-1-oxophthalazin-2(1H)yl-ones

  摘要：

  Some new benzenesulfonylthiourea derivatives substituted with phthalazones (2a-q) were synthesized by refluxing the appropriate 4-aryl-1-oxophthalazin-2(1H)yl benzenesulfonamides with isothiocyanate in dry acetone over anhydrous K2CO3. All the synthesized compounds were characterized on the basis of IR, H-1 NMR, MS data and elemental analysis. These synthesized compounds (2a-q) at the dose of 20 mg/kg were tested for antihyperglycemic activity in the glucose-fed hyperglycemic normal rat model and among these compounds 2f and 2m showed modest antihyperglycemic activity.

  DOI：

  10.3109/14756366.2013.782300
• 作为产物：
  描述：

  甲苯 在 aluminum (III) chloride 作用下， 生成 4-[4-(4-methylphenyl)-1-oxophthalazin-2(1H)-yl]-benzenesulfonamide
  参考文献：
  名称：

  Synthesis and blood glucose lowering activity of some novel benzenesulfonylthiourea derivatives substituted with 4-aryl-1-oxophthalazin-2(1H)yl-ones

  摘要：

  Some new benzenesulfonylthiourea derivatives substituted with phthalazones (2a-q) were synthesized by refluxing the appropriate 4-aryl-1-oxophthalazin-2(1H)yl benzenesulfonamides with isothiocyanate in dry acetone over anhydrous K2CO3. All the synthesized compounds were characterized on the basis of IR, H-1 NMR, MS data and elemental analysis. These synthesized compounds (2a-q) at the dose of 20 mg/kg were tested for antihyperglycemic activity in the glucose-fed hyperglycemic normal rat model and among these compounds 2f and 2m showed modest antihyperglycemic activity.

  DOI：

  10.3109/14756366.2013.782300

文献信息

• Synthesis and Biological Evaluation of 4-Arylphthalazones Bearing Benzenesulfonamide as Anti-Inflammatory and Anti-Cancer Agents
  作者：Shafiya Yaseen、Syed Ovais、Rafia Bashir、Pooja Rathore、Mohammed Samim、Surender Singh、Vinod Nair、Kalim Javed

  DOI：10.1002/ardp.201300056

  日期：2013.6

  Nine 4‐arylphthalazones bearing benzenesulfonamide (2a–i) were synthesized by the condensation of the appropriate 2‐aroylbenzoic acid (1a–i) and 4‐hydrazinobenzenesulfonamide in ethanol. The structures of these compounds were elucidated by elemental analysis, IR, 1H NMR, 13C NMR, and MS spectroscopy. Two compounds, 2b and 2i, showed significant anti‐inflammatory activity comparable to that of the standard

  通过适当的 2-芳酰基苯甲酸 (1a-i) 和 4-肼基苯磺酰胺在乙醇中的缩合，合成了九个带有苯磺酰胺 (2a-i) 的 4-芳基邻苯二甲酮。这些化合物的结构通过元素分析、IR、1H NMR、13C NMR和MS光谱进行了阐明。在角叉菜胶诱导的大鼠爪水肿模型中，两种化合物 2b 和 2i 显示出与标准药物塞来昔布相当的显着抗炎活性。这些化合物（2b 和 2i）对 COX-2 酶具有选择性抑制活性。与塞来昔布相比，化合物 2b 具有更好的选择性比（COX-1/COX-2），可用作设计选择性 COX-2 抑制剂的新模板。美国国家癌症研究所（美国）筛选了化合物 2d 和 2i 对 60 种人类癌细胞系的抗增殖活性。化合物 2d 和 2i 对肾癌细胞系 UO-31 显示出温和的活性。