4-(5-amino-3-phenyl-1H-pyrazol-1-yl)benzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-amino-3-phenyl-1H-pyrazol-1-yl)benzenesulfonamide
• 英文别名: 4-(5-amino-3-phenylpyrazol-1-yl)benzenesulfonamide
• 化学式: C₁₅H₁₄N₄O₂S
• 分子量: 314.368
• InChiKey: LTJYLJXQZYWCOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 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：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(5-amino-3-phenyl-1H-pyrazol-1-yl)benzenesulfonamide 在 碘苯二乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以76%的产率得到4-((E)-((Z)-2-cyano-1-phenylvinyl)diazenyl)benzenesulfonamide
  参考文献：
  名称：

  PIDA-mediated oxidative aromatic C N bond cleavage: Efficient methodology for the synthesis of 1,2-diaza-1,3-dienes under ambient conditions

  摘要：

  DOI：

  10.1016/j.tetlet.2021.153252
• 作为产物：
  描述：

  磺胺 在 盐酸 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 0.25h， 生成 4-(5-amino-3-phenyl-1H-pyrazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  具有令人信服的COX-2选择性和增强的胃安全性的含二芳基吡唑磺酰胺的抗炎探索

  摘要：

  合成了新型的含磺酰胺的二芳基吡唑，随后对其体外环氧合酶抑制试验进行了测试。然后，使用标准角叉菜胶诱导的大鼠爪水肿方法，对显示出令人满意的体外COX-2 IC 50值和选择性指数的化合物进行体内抗炎抑制分析。评价了两种有前途的抑制剂的致溃疡作用。COX-2的X射线晶体结构取自PDB条目COX-2（3LN1），分辨率为2.80Å（埃）。对接研究的结构准备工作是使用Maestro 9.0中的蛋白质准备向导完成的。化合物10b表现出合理的COX-2抑制作用（COX-2 IC50  = 0.52μM）和COX-2选择性指数（SI = 10.73）与塞来昔布（COX-2 IC 50  = 0.78μM）和（SI = 9.51）进行比较。体内抗炎研究显示10b的抑制率为64.28％，而塞来昔布本身的抑制率为57.14％。还发现致溃疡作用的结果与标准塞来昔布相当。分子对接研究表明，所有设计的分子均表现出与

  DOI：

  10.1002/jhet.3118

文献信息

• Exploration of antimicrobial potential of pyrazolo[3,4-b]pyridine scaffold bearing benzenesulfonamide and trifluoromethyl moieties
  作者：Navneet Chandak、Satish Kumar、Pawan Kumar、Chetan Sharma、Kamal R. Aneja、Pawan K. Sharma

  DOI：10.1007/s00044-013-0544-1

  日期：2013.11

  The synthesis and biological evaluation of a library of thirty differently substituted pyrazolo[3,4-b]pyridines bearing benzenesulfonamide moiety at position-1 and trifluoromethyl group at position-4 are reported. Fused heterocyclic system present in the target compounds (5a-j, 6a-j, and 7a-j) was constructed by refluxing various 5-aminopyrazoles (3a-c) with differently substituted trifluoromethyl-beta-diketones (4a-j) in glacial acetic acid. All the target compounds (5-7) were evaluated for their in vitro antibacterial activity against four pathogenic bacterial strains namely, Staphylococcus aureus, Bacillus subtilis (Gram-positive), Escherichia coli, Pseudomonas aeruginosa (Gram-negative) and in vitro antifungal activity against two pathogenic fungal yeasts namely, Saccharomyces cerevisiae and Candida albicans.Thirty differently substituted pyrazolo[3,4-b]pyridines bearing benzenesulfonamide moiety at position-1 and trifluoromethyl group at position-4 were synthesized and screened for antibacterial and antifungal activities.
• Synthesis and anti-inflammatory evaluation of some pyrazolo[3,4-b]pyridines
  作者：Pawan K. Sharma、Karan Singh、Surender Kumar、Pawan Kumar、S. N. Dhawan、Sukhbir Lal、Holger Ulbrich、Gerd Dannhardt

  DOI：10.1007/s00044-010-9312-7

  日期：2011.3

  Novel series of pyrazolo[3,4-b]pyridines with basic skeleton different from the known COX inhibitors were synthesized from 5-amino-1-[4-(aminosulfonyl)phenyl]-3-phenyl-1H-pyrazole, which in turn was prepared by the condensation of (4-sulfamoylphenyl)hydrazine with alpha-cyanoacetophenone. All the newly synthesized compounds were tested for their in vivo anti-inflammatory activity by carrageenan-induced rat paw edema assay. Some of the most potent compounds were evaluated in different COX and LOX assays. Some of the new compounds were found to possess moderate anti-inflammatory activity.
• COMBINATIONS COMPRISING AN HSP90 INHIBITOR AND A PHOPHODIESTERASE INHIBITOR FOR TREATING OR PREVENTING NEOPLASIA
  申请人：Pharmacia Corporation

  公开号：EP1682143A2

  公开（公告）日：2006-07-26
• [EN] COMBINATIONS COMPRISING AN Hsp90 INHIBITOR AND A PHOPHODIESTERASE INHIBITOR FOR TREATING OR PREVENTING NEOPLASIA<br/>[FR] ASSOCIATION DE L'INHIBITEUR DE HSP90 ET DE L'INHIBITEUR DE LA PHOPHODIESTERASE DESTINEE A TRAITER OU PREVENIR LA NEOPLASIE
  申请人：PHARMACIA CORP

  公开号：WO2005041879A2

  公开（公告）日：2005-05-12

  A method for treating or preventing neoplasia or a neoplasia-related disorder in a subject is provided, the method comprising administering to the subject an effective amount of a combination comprising an Hsp90 inhibitor and a phosphodiesterase inhibitor, and optionally a Cox-2 inhibitor.
• [EN] TREATMENT OR PREVENTION OF NEOPLASIA BY USE OF AN Hsp90 INHIBITOR<br/>[FR] TRAITEMENT OU PREVENTION DE LA NEOPLASIE A L'AIDE D'UN INHIBITEUR DE LA PROTEINE HSP90
  申请人：PHARMACIA CORP

  公开号：WO2005044194A2

  公开（公告）日：2005-05-19

  A method for treating or preventing neoplasia or a neoplasia-related disorder in a subject is provided, the method comprising administering to the subject an effective amount of an Hsp90 inhibitor, or of a combination comprising an Hsp90 inhibitor and a Cox-2 inhibitor.