4-(3-(3,4-dichlorophenyl)-6-oxo-5,6-dihydropyridazin-1(4H)-yl)benzenesulfonamide | 1355614-11-7

• 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: 4-(3-(3,4-dichlorophenyl)-6-oxo-5,6-dihydropyridazin-1(4H)-yl)benzenesulfonamide
• 英文别名: 6-(3',4'-dichlorophenyl)-2-(4-sulfamoylphenyl)-4,5-dihydropyridazin-3(2H)-one；4-[3-(3,4-Dichlorophenyl)-6-oxo-4,5-dihydropyridazin-1-yl]benzenesulfonamide
• CAS: 1355614-11-7
• 化学式: C₁₆H₁₃Cl₂N₃O₃S
• 分子量: 398.27
• InChiKey: RCMFZCLVTRBJDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  邻二氯苯 在 aluminum (III) chloride 作用下， 以 乙醇 为溶剂， 反应 54.5h， 生成 4-(3-(3,4-dichlorophenyl)-6-oxo-5,6-dihydropyridazin-1(4H)-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and biological evaluation of some novel sulfamoylphenyl-pyridazinone as anti-inflammatory agents (Part-II)

  摘要：

  Seven novel 6-aryl-2-(p-sulfamoylphenyl)-4,5-dihydropyridazin-3(2H)-ones (2a-g) were synthesized by the condensation of appropriate aroylpropionic acid and 4-hydrazinobenzenesulfonamide hydrochloride in ethanol. Structure of all compounds have been elucidated by elemental analysis, IR, H-1 NMR, C-13 NMR, DEPT and MS spectrscopy. These compounds were tested for their anti-inflammatory activity in carrageenan-induced rat paw edema model. Compound 2b exhibited anti-inflammatory activity comparable to that of celecoxib (at 5 h). Two other compounds 2d and 2g showed promising anti-inflammatory activity (edema reduction more than 80% at 5 h). These compounds (2b, 2d and 2g) did not produce any ulceration in gastric region.

  DOI：

  10.3109/14756366.2011.577036

文献信息

• Pyridazinone-substituted benzenesulfonamides display potent inhibition of membrane-bound human carbonic anhydrase IX and promising antiproliferative activity against cancer cell lines
  作者：Mikhail Krasavin、Anton Shetnev、Sergey Baykov、Stanislav Kalinin、Alessio Nocentini、Vladimir Sharoyko、Giulio Poli、Tiziano Tuccinardi、Mikhail Korsakov、Tatiana B. Tennikova、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2019.02.044

  日期：2019.4

  concentration-dependent mode against normal (ARPE-19) and two cancer cell lines (PANC-1 and SK-MEL-2) identified two lead compounds one of which displayed a notable cytotoxicity toward pancreatic cancer cells while the other targeted the melanoma cells. These findings significantly expand the knowledge base concerning the hCA IX inhibitors whose inhibitory potency against a recombinant enzyme translates

  研究了一组扩展的含哒嗪的苯磺酰胺类化合物对四种人类碳酸酐酶同工型的抑制作用，揭示了对h的明显抑制趋势。CA IX，一种与癌症相关的膜结合酶。比较这些化合物对浓度为50μM的癌细胞（PANC-1）和正常细胞（ARPE-19）的抗增殖作用，将化合物的选择范围缩小到了显示对癌细胞具有选择性生长抑制作用的八种化合物。在针对浓度正常的模式下针对正常（ARPE-19）和两种癌细胞系（PANC-1和SK-MEL-2）进行了更详细的研究，发现了两种先导化合物，其中一种对胰腺癌细胞显示出明显的细胞毒性，而另一种针对黑色素瘤细胞。
• Synthesis and biological evaluation of some novel sulfamoylphenyl-pyridazinone as anti-inflammatory agents (Part-II)
  作者：Rafia Bashir、Shafiya Yaseen、Syed Ovais、Shamim Ahmad、Hinna Hamid、M.S. Alam、Mohammad Samim、Kalim Javed

  DOI：10.3109/14756366.2011.577036

  日期：2012.2.1

  Seven novel 6-aryl-2-(p-sulfamoylphenyl)-4,5-dihydropyridazin-3(2H)-ones (2a-g) were synthesized by the condensation of appropriate aroylpropionic acid and 4-hydrazinobenzenesulfonamide hydrochloride in ethanol. Structure of all compounds have been elucidated by elemental analysis, IR, H-1 NMR, C-13 NMR, DEPT and MS spectrscopy. These compounds were tested for their anti-inflammatory activity in carrageenan-induced rat paw edema model. Compound 2b exhibited anti-inflammatory activity comparable to that of celecoxib (at 5 h). Two other compounds 2d and 2g showed promising anti-inflammatory activity (edema reduction more than 80% at 5 h). These compounds (2b, 2d and 2g) did not produce any ulceration in gastric region.