2,6-dimethyl-4-(3-nitrophenyl)-3-(phenylcarbamoyl)-5-(carbomethoxy)-1,4-dihydropyridine | 116400-31-8

• 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: 2,6-dimethyl-4-(3-nitrophenyl)-3-(phenylcarbamoyl)-5-(carbomethoxy)-1,4-dihydropyridine
• 英文别名: methyl 2,6-dimethyl-4-(3-nitrophenyl)-5-(phenylcarbamoyl)-1,4-dihydropyridine-3-carboxylate
• CAS: 116400-31-8
• 化学式: C₂₂H₂₁N₃O₅
• 分子量: 407.426
• InChiKey: JWGFAXLURWPCSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  110.57
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  N-乙酰乙酰苯胺 在 吡啶 作用下， 以 1,4-二氧六环 、 异丙醇 为溶剂， 生成 2,6-dimethyl-4-(3-nitrophenyl)-3-(phenylcarbamoyl)-5-(carbomethoxy)-1,4-dihydropyridine
  参考文献：
  名称：

  Synthesis and 3D-QSAR study of 1,4-dihydropyridine derivatives as MDR cancer reverters

  摘要：

  A series of symmetrical and unsymmetrical 1,4-dihydropyridines were synthesized by a rapid, single pot microwave irradiation (MWI) based protocol along with conventional approach and characterized by NMR, IR and mass spectroscopic techniques. The compounds were evaluated for their tumor cell cytotoxicity in HL-60 tumor cells. A 3D-QSAR study using CoMFA and CoMSIA was carried out to decipher the factors governing MDR reversing ability in cancer. The resulting contour maps derived by the best 3D-QSAR models provide a good insight into the molecular features relevant to the biological activity in this series of analogs. 3D contour maps as a result of 3D-QSAR were utilized to identify some novel features that can be incorporated into the 1,4-dihydropyridine framework to enhance the activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.011

文献信息

• Synthesis and Structural Conformation Studies of a Potent Unsymmetrical 1,4-Dihydropyridine
  作者：S. Naveen、Sridhar M. Anandalwar、J. Shashidhara Prasad、Dinesh Manvar、Arun Mishra、Anamik Shah

  DOI：10.1007/s10870-008-9314-1

  日期：2008.4

  2,6-Dimethyl-5-(phenylcarbamoyl)-4-(3-nitrophenyl)-1,4-dihydropyridine-2-carboxylate was synthesized in two steps and was characterized spectroscopically and confirmed by X-ray diffraction studies. The molecule crystallizes in the monoclinic crystal class in the spacegroup P21/c with cell parameters a = 10.5960(6) Å, b = 10.2450(7) Å, c = 19.5790(11) Å, β = 107.448(3)° and Z = 4. The 1,4-dihydropyridine ring in the structure adopts a flattened boat conformation. 2,6-Dimethyl-5-(phenylcarbamoyl)-4-(3-nitrophenyl)-1,4-dihydropyridine-2-carboxylate was synthesized in two steps and was characterized spectroscopically and confirmed by X-ray diffraction studies. The molecule crystallizes in the monoclinic crystal class in the spacegroup P21/c with cell parameters a = 10.5960(6) Å, b = 10.2450(7) Å, c = 19.5790(11) Å, β = 107.448(3)° and Z = 4. The 1,4-dihydropyridine ring in the structure adopts a flattened boat conformation.

  2,6-二甲基-5-(苯基氨基甲酰基)-4-(3-硝基苯基)-1,4-二氢吡啶-2-羧酸酯通过两步合成，并通过光谱学和X射线衍射研究进行表征和确认。该分子在单斜晶类中以空间群P21/c结晶，晶胞参数为a=10.5960(6)Å、b=10.2450(7)Å、c=19.5790(11)Å、β=107.448(3)°和Z=4。结构中的1,4-二氢吡啶环采用扁平船形构象。2,6-二甲基-5-(苯基氨基甲酰基)-4-(3-硝基苯基)-1,4-二氢吡啶-2-羧酸酯通过两步合成，并通过光谱学和X射线衍射研究进行表征和确认。该分子在单斜晶类中以空间群P21/c结晶，晶胞参数为a=10.5960(6)Å、b=10.2450(7)Å、c=19.5790(11)Å、β=