diethyl 1-phenyl-4-(4-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate | 832124-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: diethyl 1-phenyl-4-(4-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: diethyl 4-(4-fluorophenyl)-1-phenyl-1,4-dihydropyridine-3,5-dicarboxylate；diethyl 4-(4-fluorophenyl)-1-phenyl-4H-pyridine-3,5-dicarboxylate
• CAS: 832124-06-8
• 化学式: C₂₃H₂₂FNO₄
• 分子量: 395.43
• InChiKey: ULHPOTZMKCALTM-UHFFFAOYSA-N

物化性质

• 沸点：
  496.7±45.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diethyl 1-phenyl-4-(4-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 以 四氢呋喃 、 甲醇 为溶剂， 以63%的产率得到tetraethyl 3,9-diphenyl-6,12-bis(4-fluorophenyl)-3,9-diazapentacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane-1,5,7,11-tetracarboxylate
  参考文献：
  名称：

  Synthesis and Biological Activity of 3,9-Diazatetraasteranes as Novel EGFR Tyrosine Kinase Inhibitors

  摘要：

  DOI：

  10.1134/s1070363222030124
• 作为产物：
  描述：

  对氟苯甲醛 、 苯胺 、 丙炔酸乙酯 以 溶剂黄146 为溶剂， 反应 0.42h， 以21.6%的产率得到diethyl 1-phenyl-4-(4-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Design, Synthesis and Biological Evaluation of 3,9-diazatetraasteranes as Novel Matrilysin Inhibitors

  摘要：

  Matrilysin is an ideal biological target to develop novel inhibitors because it is overexpressed in malignant tumour cells. A series of 3,9‐diazatetraasteranes was designed as inhibitors of matrilysin, which was an ideal biological target because it is responsible for aggressive malignant phenotypes and poor prognoses implicated in many cancers. Docking simulation supported the initial pharmacophore hypothesis and suggested a common interaction mechanism of 3,9‐diazatetraasteranes with the catalytic site of matrilysin. The 3,9‐diazatetraasteranes were synthesized by the photocyclization of 4‐aryl‐1,4‐dihydropyridines, and their structures were determined using 1H NMR, 13C NMR and MS. The inhibitory activities of these compounds on matrilysin were investigated in vitro using an MTT assay in A549 (small cell lung cancer) cells. The results show that the 3,9‐diazatetraasteranes can inhibit the growth of A549 tumour cells. The best IC50 value is approximately 50 μm. This result indicates that 3,9‐diazatetraasteranes will be useful pharmacological tools for the investigation of matrilysin inhibitors.

  DOI：

  10.1111/cbdd.12185

文献信息

• Manipulating [2 + 2] photodimerization of 1,4-dihydropyridines within γ -cyclodextrin
  作者：Wuji Sun、Qiangwen Fan、Hong Yan

  DOI：10.1016/j.jphotochem.2018.03.046

  日期：2018.5

  volume in γ-CD is responsible for the observed selectivity. The formation of 1:2 host-guest inclusion complex plays an important role in this reaction, and manipulates DHPs to perform [2 + 2] photodimerization as expected. In order to investigate the inclusion process, the spectral characteristics were investigated and the theoretical study was performed using density functional theory (DFT).

  在γ-环糊精（γ -CD）存在下照射1,4-二氢吡啶（DHP）可以在中压汞灯下有效形成笼状二聚体。γ -CD中复合的DHP的笼二聚体产率可达到约80％，远高于非复合状态的DHP 。假设可用的腔体体积为γ-CD负责观察到的选择性。1：2宿主-客体包含复合物的形成在此反应中起重要作用，并按预期操作DHP进行[2 + 2]光二聚。为了研究包含过程，研究了光谱特征，并使用密度泛函理论（DFT）进行了理论研究。
• Design, Synthesis and Biological Evaluation of 3,9-diazatetraasteranes as Novel Matrilysin Inhibitors
  作者：Yanlan Liu、Hongbo Tan、Hong Yan、Xiuqing Song

  DOI：10.1111/cbdd.12185

  日期：2013.11

  Matrilysin is an ideal biological target to develop novel inhibitors because it is overexpressed in malignant tumour cells. A series of 3,9‐diazatetraasteranes was designed as inhibitors of matrilysin, which was an ideal biological target because it is responsible for aggressive malignant phenotypes and poor prognoses implicated in many cancers. Docking simulation supported the initial pharmacophore hypothesis and suggested a common interaction mechanism of 3,9‐diazatetraasteranes with the catalytic site of matrilysin. The 3,9‐diazatetraasteranes were synthesized by the photocyclization of 4‐aryl‐1,4‐dihydropyridines, and their structures were determined using 1H NMR, 13C NMR and MS. The inhibitory activities of these compounds on matrilysin were investigated in vitro using an MTT assay in A549 (small cell lung cancer) cells. The results show that the 3,9‐diazatetraasteranes can inhibit the growth of A549 tumour cells. The best IC50 value is approximately 50 μm. This result indicates that 3,9‐diazatetraasteranes will be useful pharmacological tools for the investigation of matrilysin inhibitors.
• Synthesis and Biological Activity of 3,9-Diazatetraasteranes as Novel EGFR Tyrosine Kinase Inhibitors
  作者：Li Mao、Nana Tian、Chaochun Wei、Hongjun Wang、Hong Yan

  DOI：10.1134/s1070363222030124

  日期：2022.3