3-(4-chlorophenyl)-5-(4-dimethylaminophenyl)-1-phenyl-2-pyrazoline

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(4-chlorophenyl)-5-(4-dimethylaminophenyl)-1-phenyl-2-pyrazoline
• 英文别名: 4-(3-(4-chlorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)-N,N-dimethylaniline；4-[5-(4-chlorophenyl)-2-phenyl-3,4-dihydropyrazol-3-yl]-N,N-dimethylaniline
• 化学式: C₂₃H₂₂ClN₃
• 分子量: 375.901
• InChiKey: OCLKWPRGEPXEIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  18.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氯苯乙酮 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 1.17h， 生成 3-(4-chlorophenyl)-5-(4-dimethylaminophenyl)-1-phenyl-2-pyrazoline
  参考文献：
  名称：

  一种改进且方便的制备N-苯基吡唑啉衍生物的方法

  摘要：

  DOI：

  10.1007/s10593-006-0176-1

文献信息

• A Potent EGFR Inhibitor, N-Phenyl Pyrazoline Derivative Suppresses Aggressiveness and Cancer Stem Cell-Like Phenotype of Cervical Cancer Cells
  作者：- Mustofa、Pamungkas Bagus Satriyo、Artania Adnin Tri Suma、Stephanus Satria Wira Waskitha、Tutik Dwi Wahyuningsih、Eti Nurwening Sholikhah

  DOI：10.2147/dddt.s350913

  日期：——

  Objective: Metastasis causes approximately 90% of cancer-related deaths, including in cervical cancer patients. Uncontrolled cell proliferation, migration, and cancer stemness act as critical events in primary tumor growth and cancer metastasis progression in cervical cancer. Here, we investigated the anti-proliferative, anti-migration, and cancer stemness inhibition activity of N-phenyl pyrazoline derivatives against cervical cancer cells. Methods: The chalcone and phenylhydrazine were used to synthesize the N-phenyl pyrazoline 2/5 (P2 and P5). The MTT, colony formation, and wound healing assays were performed to evaluate the N-phenyl pyrazoline effect in HeLa cells. The N-phenyl pyrazoline's protein target was predicted using SwissTargetPrediction and AutoDock Vina software. The Western blotting assay was performed to evaluate the target proteins. The public dataset analysis was used to confirm the clinical relevance of target protein in cervical cancer patients. Results: N-phenyl pyrazoline 2 and 5 were successfully synthesized. The N-phenyl pyrazolines 2 and 5 exhibit cytotoxic effect in HeLa cell line with 20.26 µM, 4.708 µM of IC50, respectively. Further study shows that the N-phenyl pyrazoline 5 suppresses the cell proliferation and migration ability of HeLa cell line in a dose-dependent manner. Target prediction and molecular docking reveal that EGFR and ERBB2 protein as the main target of the N-phenyl pyrazoline 5 compound. The N-phenyl pyrazoline 5 suppresses the EGFR expression level but not the total ERK1/2. Public data and GSEA analysis found that the EGFR high expression level is positively associated with poor survival, cancer metastasis-related signaling pathways, and cancer stem cell markers in cervical cancer patients. In addition, the N-phenyl pyrazoline 5 reduces the HeLa's tumorsphere size and cancer stem cell marker, CD133. Conclusion: N-phenyl pyrazoline 5 suppresses the cell viability, proliferation, migration, and cancer stem cell-like phenotype of cervical cancer cells via EGFR inhibition.