diethyl 1-(4-methylphenyl)-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate | 136886-13-0

• 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-(4-methylphenyl)-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: diethyl 1-(4-methylphenyl)-4-phenyl-4H-pyridine-3,5-dicarboxylate
• CAS: 136886-13-0
• 化学式: C₂₄H₂₅NO₄
• 分子量: 391.467
• InChiKey: GVHSHQMFPZTOES-UHFFFAOYSA-N

物化性质

• 沸点：
  521.6±50.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 1-(4-methylphenyl)-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate 以 四氢呋喃 、 甲醇 为溶剂， 以42.7%的产率得到tetraethyl 3,9-di(4-methylphenyl)-6,12-diphenyl-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：

  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
• 作为产物：
  描述：

  BENZAL-P-TOLUIDINE 、 丙炔酸乙酯 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 various solvent(s) 为溶剂， 反应 24.0h， 以62%的产率得到diethyl 1-(4-methylphenyl)-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Catalytic synthesis of 1,4-dihydropyridine derivatives using scandium(III) triflate

  摘要：

  Scandium(III) triflate smoothly catalyzed the reaction of imines with ethyl propiolate (2.5 equiv) to produce the corresponding N-substituted 1,4-dihydropyridines in good yields in toluene or BTF under reflux conditions. It also catalyzed the reaction of aniline and ethyl propiolate (3.2 equiv) to give another 1,4-dihydropyridine bearing three ester groups in moderate yield under the same conditions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.003

文献信息

• Domino Reaction of 3-(2-Formylphenoxy)propenoates and Amines:  A Novel Synthesis of 1,4-Dihydropyridines from Salicaldehydes, Ethyl Propiolate, and Amines
  作者：Sun-Liang Cui、Jun Wang、Xu-Feng Lin、Yan-Guang Wang

  DOI：10.1021/jo7013593

  日期：2007.9.1

  [GRAPHICS]A novel synthesis of Hantzsch-type N-substituted 1,4-dihydropyridines from salicaldehydes, ethyl propiolate, and amines has been developed. Salicaldehydes were treated with ethyl propiolate in the presence of N-methylmorpholine to give ethyl 3-(2-formylphenoxy)propenoates. Three equivalents of ethyl 3-(2-formylphenoxy)propenoates reacted with 1 equiv of amines under trifluoroacetic acid (TFA) catalyst to furnish the corresponding N-substituted 1,4-dihydropyridines in good to excellent yields, recovering the starting material salicaldehydes. A possible mechanism for the domino process was proposed. Furthermore, the products can be easily derived via further transformations and three of them exhibited strong fluorescence (Phi(f) = 0.36-0.63).
• Synthesis and electrochemical oxidation of 1-aryl-3,5-diethoxycarbonyl-2,6-unsubstituted 1,4-dihydropyridines
  作者：B. S. Chekavichus、A. � Sausin'sh、V. P. Kadysh、G. Ya. Dubur、Ya. P. Stradyn'

  DOI：10.1007/bf00474235

  日期：1991.3
• Biological evaluation of 4-aryl-1,4-dihydropyridines as VEGFR-2 kinase inhibitors
  作者：W. Sun、Z. Ma、H. Yan

  DOI：10.1134/s1070363216120574

  日期：2016.12

  Vascular endothelial growth factor-2 receptor (VEGFR-2) kinase is a promising target for the development of novel anticancer drugs. Molecular docking modeling was performed on a series of 4-aryl-1,4-dihydropyridines derivatives to evaluate the structural basis for VEGFR-2 inhibitory activity. Some 4-aryl-1,4-dihydropyridines were synthesized in the reaction of aromatic aldehydes and ethyl propiolate with anilines in acetic acid. The biological activities were evaluated against the cells A549, A431 and Hep-G2. The results indicated that 4-aryl-1,4-dihydropyridines could be the promising potential VEGFR-2 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
• SAUSIN A. EH.; CHEKAVICHUS B. S.; LUSIS V. K.; DUBUR G. YA., XIMIYA GETEROTSIKL. SOEDIN., 1980, HO 4, 493-501
  作者：SAUSIN A. EH.、 CHEKAVICHUS B. S.、 LUSIS V. K.、 DUBUR G. YA.

  DOI：——

  日期：——