4-(5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide | 111607-58-0

• 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-(5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide
• 英文别名: 4-[5-(4-Chlorophenyl)-3-phenyl-2-pyrazolin-1-yl]benzenesulfonamide；4-[3-(4-chlorophenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]benzenesulfonamide
• CAS: 111607-58-0
• 化学式: C₂₁H₁₈ClN₃O₂S
• 分子量: 411.912
• InChiKey: OLNQHQDGYZJVST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide 在 溴 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 生成 1-[4-[5-(4-chlorophenyl)-3-phenylpyrazol-1-yl]phenyl]sulfonyl-3-prop-2-enylthiourea
  参考文献：
  名称：

  新型取代的3,5-二芳基吡唑磺酰脲衍生物的制备及抗糖尿病活性。II：结构-活性关系。

  摘要：

  制备了四个取代的对-（3,5-二芳基-2-吡唑啉-1）苯磺酰脲和硫脲衍生物系列，以及它们相应的取代的对-（3,5-二芳基吡唑-1）苯磺酰脲和硫脲衍生物，以评估为降糖药。初步生物学测试表明，新化合物具有有效的降血糖活性。

  DOI：

  10.1002/jps.2600760808
• 作为产物：
  描述：

  4-氯查耳酮 在 盐酸 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 4-(5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  新型取代的3,5-二芳基吡唑磺酰脲衍生物的制备及抗糖尿病活性。II：结构-活性关系。

  摘要：

  制备了四个取代的对-（3,5-二芳基-2-吡唑啉-1）苯磺酰脲和硫脲衍生物系列，以及它们相应的取代的对-（3,5-二芳基吡唑-1）苯磺酰脲和硫脲衍生物，以评估为降糖药。初步生物学测试表明，新化合物具有有效的降血糖活性。

  DOI：

  10.1002/jps.2600760808

文献信息

• Synthesis, Molecular Docking Study, and Cytotoxic Activity of 1,3,5-triaryl Pyrazole Derivatives
  作者：Maryam Ghasemi、Sajad Ghadbeighi、Amirali Amirhamzeh、Seyed AbbasTabatabai、Seyed Nasser Ostad、Abbas Shafiee、Mohsen Amini

  DOI：10.2174/1570180812666150722235902

  日期：2015.11.12

  Synthesis, molecular docking study, and cytotoxic activity of a new group of 1,3,5-triaryl pyrazole derivatives were be studied. The antiproliferative activity of the final compounds were examined in MCF-7, AGS, HT-29 and NIH3T3 cell lines by MTT assay, using different concentrations of each compound to determine their IC50 . The cytotoxic activity of paclitaxel and doxorubicin were evaluated as positive

  研究了一组新的1,3,5-三芳基吡唑衍生物的合成，分子对接研究和细胞毒性。通过MTT测定法在MCF-7，AGS，HT-29和NIH3T3细胞系中检查最终化合物的抗增殖活性，使用不同浓度的每种化合物确定其IC 50。紫杉醇和阿霉素的细胞毒性活性被评估为阳性对照。所有化合物均以剂量依赖性方式在所述细胞系中显示出细胞毒活性。在所有具有IC 50的癌细胞系中，化合物（5j，5b和5d）显示出最高的细胞毒性小于5.0μM。此外，最有效的化合物之一化合物5g对NIH3T3细胞系（一种非癌性细胞系）显示出令人惊讶的低细胞毒性作用。总之，我们的数据表明，合成的化合物具有针对癌细胞的部分选择性作用机制，并且可能对正常细胞具有较低的毒性作用，这使其成为合成其新衍生物的有趣候选物。 在分子建模中，研究将所有合成的化合物停靠在微管蛋白α和β链的秋水仙碱结合位点，并计算了预测的结合能。我们的数据表明这些衍生物可能会提出有前途的化学治疗剂，可能靶向微管。
• Inhibitors of Yellow Fever Virus replication based on 1,3,5-triphenyl-4,5-dihydropyrazole scaffold: Design, synthesis and antiviral evaluation
  作者：Rossella Fioravanti、Nicoletta Desideri、Antonio Carta、Elena Maria Atzori、Ilenia Delogu、Gabriella Collu、Roberta Loddo

  DOI：10.1016/j.ejmech.2017.09.060

  日期：2017.12

  By the antiviral screening of an in house library of pyrazoline compounds, 4-(3-(4-phenoxyphenyl)-5pheny1-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide (5a) was identified as a promising hit compound for the development of anti-Yellow Fever Virus (YFV) agents. Structural optimization studies were focused on the development of 5a analogues which retain the potency as YFV inhibitors and show a reduced cytotoxicity. The synthesized 1-3,5-triphenyl-pyrazolines (4a-j, 5a-j, 6a-j) were evaluated in cell based assays for cytotoxicity and antiviral activity against representative viruses of two of the three genera of the Flaviviridae family, i.e.: Pestivirus (BVDV) and Flavivirus (YFV). These compounds were also tested against a large panel of different pathogenic RNA and DNA viruses. Most of the new 1-3,5-triphenyl-pyrazolines (4a-j, 5a j, 6a-j) exhibited a specific activity against YFV, showing EC50 values in the low micromolar range with almost a 10-fold improvement in potency compared to the reference inhibitor 6-azauridine. However, the selectivity indexes of the unsubstituted (4a-j) and the phenoxy (5a-j) analogues were generally modest due to the pronounced cytotoxicity against BHK-21 cells. Otherwise, the benzyloxy derivatives (6a-j) generally coupled high potency and selectivity. On the basis of both anti-YFV activity and selectivity index, pyrazolines 6a and 6b were chosen for time of addition experiments. The selected pyrazolines and the reference inhibitor 6-azauridine displayed maximal inhibition when added in the pretreatment or during the infection. (C) 2017 Elsevier Masson SAS. All rights reserved.
• SOLIMAN, RAAFAT;FAID-ALLAH, HASSAN M.;EL, SADANY SAMIR K., J. PHARM. SCI., 76,(1987) N 8, 626-632
  作者：SOLIMAN, RAAFAT、FAID-ALLAH, HASSAN M.、EL, SADANY SAMIR K.

  DOI：——

  日期：——
• US9642835B2
  申请人：——

  公开号：US9642835B2

  公开（公告）日：2017-05-09
• Preparation and Antidiabetic Activity of New Substituted 3,5-Diarylpyrazolesulfonylurea Derivatives II: Structure-Activity Relationship
  作者：Raafat Soliman、Hassan M. Faid-Allah、Samir K. El Sadany

  DOI：10.1002/jps.2600760808

  日期：1987.8

  Four series of substituted p-(3,5-diaryl-2-pyrazoline-1) benzenesulfonylurea and thiourea derivatives, along with their corresponding substituted p-(3,5-diarylpyrazole-1) benzenesulfonylurea and thiourea derivatives, were prepared for evaluation as hypoglycemic agents. Preliminary biological testing revealed that the new compounds possess potent hypoglycemic activity.

  制备了四个取代的对-（3,5-二芳基-2-吡唑啉-1）苯磺酰脲和硫脲衍生物系列，以及它们相应的取代的对-（3,5-二芳基吡唑-1）苯磺酰脲和硫脲衍生物，以评估为降糖药。初步生物学测试表明，新化合物具有有效的降血糖活性。