4-[3-(4-甲基苯基)-5-苯基-3,4-二氢吡唑-2-基]苯磺酰胺 | 111607-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[3-(4-甲基苯基)-5-苯基-3,4-二氢吡唑-2-基]苯磺酰胺
• 英文名称: 4-[3-(4-methylphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]benzene sulfonamide
• 英文别名: 4-(3-phenyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide；4-[3-(4-Methylphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]benzenesulfonamide
• CAS: 111607-57-9
• 化学式: C₂₂H₂₁N₃O₂S
• 分子量: 391.494
• InChiKey: MBSCPVGGCCNQCY-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C(Solvent: Ethanol)
• 沸点：
  606.7±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 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-[3-(4-甲基苯基)-5-苯基-3,4-二氢吡唑-2-基]苯磺酰胺 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 生成 4-(3-phenyl-5-p-tolyl-1H-pyrazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  1,3,5-三芳基吡唑衍生物的合成，分子对接研究和细胞毒活性

  摘要：

  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。

  DOI：

  10.2174/1570180812666150722235902
• 作为产物：
  描述：

  4-(2-(1-phenyl-3-(p-tolyl)allylidene)hydrazinyl)benzenesulfonamide 在 盐酸 作用下， 反应 1.0h， 以88%的产率得到4-[3-(4-甲基苯基)-5-苯基-3,4-二氢吡唑-2-基]苯磺酰胺
  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 of sulfonamides bearing 1,3,5-triarylpyrazoline and 4-thiazolidinone moieties as novel antimicrobial agents
  作者：Thi-Dan Thach、Thi Le、Thien-Annguyen Nguyen、Chi-Hien Dang、Van-Su Dang、Thanh-Danh Nguyen

  DOI：10.2298/jsc180621057t

  日期：——

  Two series of sulfonamides were synthesized from 4-hydrazinylbenzenesulfonamide as the key starting material. 1,3,5-Triarylpyrazoline sulfonamides (2a?i) were obtained by cyclocondensation of various chalcones in 53? ?64 % yields, while 4-thiazolidinone derivatives (4a?e) were synthesized by cyclocondensation between mercaptoacetic acid and different phenylhydrazones in 43?62 % yields. The synthesized compounds were characterized based on FTIR, 1H-NMR, 13C-NMR and HRMS data. The sulfonamides were evaluated for their in vitro antimicrobial activities against four bacterial strains (E. coli, P. aeruginosa, B. subtillis and S aureus), two filamentous fungal strains (A. niger and F. oxysporum) and two yeast strains (C. albicans and S. cerevisiae). Seven pyrazolines, 2a?c and 2e?h, exhibited significant inhibition of different microbial strains. Among them, compound 2b displayed good antifungal activity against A. niger (MIC value at 12.5 ?g mL-1) over the reference drug.

  以 4- 肼基苯磺酰胺为关键起始原料，合成了两个系列的磺酰胺类化合物。1,3,5-三芳基吡唑啉磺酰胺（2a?i）由不同的查耳酮环缩合而成，收率为 53% 至 64%；4-噻唑烷酮衍生物（4a?e）由巯基乙酸和不同的苯肼环缩合而成，收率为 43% 至 62%。根据傅立叶变换红外光谱、1H-NMR、13C-NMR 和 HRMS 数据对合成的化合物进行了表征。评估了磺酰胺类化合物对四种细菌菌株（大肠杆菌、绿脓杆菌、枯草杆菌和金黄色葡萄球菌）、两种丝状真菌菌株（黑木耳和氧孢子菌）以及两种酵母菌菌株（白僵菌和酿酒酵母）的体外抗菌活性。2a?c 和 2e?h 这七种吡唑类化合物对不同的微生物菌株有显著的抑制作用。其中，化合物 2b 对 A. niger（MIC 值为 12.5?g mL-1）的抗真菌活性优于参考药物。
• 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。