4-[5-amino-4-[(3,5-dimethyl-1H-pyrazol-1-yl)carbonyl]-1H-pyrazol-1-yl]benzenesulfonamide | 1160498-18-9

• 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-4-[(3,5-dimethyl-1H-pyrazol-1-yl)carbonyl]-1H-pyrazol-1-yl]benzenesulfonamide
• 英文别名: 4-[5-amino-4-(3,5-dimethylpyrazole-1-carbonyl)pyrazol-1-yl]benzenesulfonamide
• CAS: 1160498-18-9
• 化学式: C₁₅H₁₆N₆O₃S
• 分子量: 360.396
• InChiKey: ZGBCFVVUXMPJEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-氨基-1-(4-氨磺酰基苯基)吡唑-4-甲酸乙酯 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 4-[5-amino-4-[(3,5-dimethyl-1H-pyrazol-1-yl)carbonyl]-1H-pyrazol-1-yl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of new pyrazolyl benzenesulfonamides linked to polysubstituted pyrazoles and thiazolidinones as anti-inflammatory and analgesic agents

  摘要：

  New compounds comprising the pyrazolyl benzenesulfonamide scaffold linked to polysubstituted pyrazoles and thiazolidinones were synthesized and evaluated for their anti-inflammatory and analgesic activities. The results revealed that most of the compounds displayed distinctive anti-inflammatory and analgesic activity. Two thiazolidinone derivatives emerged with the highest anti-inflammatory activity in this study, whereas two pyrazole derivatives displayed high analgesic activity with a fast onset of action compared to the reference drug. Moreover, the active compounds showed minimal potential for gastric injury in addition to a good safety margin (ALD(50) >0.25 g/kg). In vitro COX-1/COX-2 inhibition study revealed that the most active compounds showed relatively more selectivity toward COX-2 than COX-1. Among the test compounds, a thiazolidinone derivative possessed the lowest IC50 value against both COX-1 and COX-2.[GRAPHICS].

  DOI：

  10.1007/s00706-015-1549-x

文献信息

• Synthesis and Biological Evaluation of Novel Pyrazoles and Pyrazolo[3,4-<i>d</i>]pyrimidines Incorporating a Benzenesulfonamide Moiety
  作者：Hayam M. A. Ashour、Abeer E. Abdel Wahab

  DOI：10.1002/ardp.200800178

  日期：2009.4

  Synthesis and biological evaluation of novel pyrazoles and pyrazolo[3,4‐d]pyrimidines are reported. Fourteen compounds were selected by the NCI and tested for their preliminary in‐vitro anticancer activity, whereas all the synthesized compounds were evaluated for their in‐vitro antimicrobial activity. Compound 12a was proven to possess the highest anticancer activity with a broad spectrum profile.

  报道了新型吡唑和吡唑并[3,4-d]嘧啶的合成和生物学评价。NCI 选择了 14 种化合物并测试了它们的初步体外抗癌活性，而所有合成的化合物都进行了体外抗微生物活性的评估。化合物 12a 被证明具有最高的抗癌活性和广谱特性。它对白血病 HL-60 (TB)、K-562、非小细胞肺癌 NCI-H23 和结肠癌 HT 29、KM 12 细胞系（GI50 = 6.59、4.44、1.37、3.33 和 9.63）特别有效μM，分别）。在合成的化合物中，发现 13 种衍生物表现出明显的抗菌活性，尤其是对铜绿假单胞菌。化合物 2c、5b、10、11b、17b、18b、并且 19 被证明是最活跃的，活动范围很广。发现化合物 19 与氨苄西林对枯草杆菌的作用等效，而化合物 11b 和 19 对铜绿假单胞菌的作用是氨苄西林的四倍，而化合物 5b 和 18b 对同一生物体的作用与氨苄西林等效。此外，化合物 2c、10