1,2,6-trimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester | 30131-51-2

• 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: 1,2,6-trimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
• 英文别名: Diethyl 1,2,6-trimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate；diethyl 1,2,6-trimethyl-4-(3-nitrophenyl)-4H-pyridine-3,5-dicarboxylate
• CAS: 30131-51-2
• 化学式: C₂₀H₂₄N₂O₆
• mdl: MFCD00356555
• 分子量: 388.42
• InChiKey: PHAPNFPDYXSDJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2,6-trimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 在 高氯酸 、 双氧水 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以45%的产率得到3,5-bis-ethoxycarbonyl-1,2,6-trimethyl-4-(3-nitro-phenyl)-pyridinium; perchlorate
  参考文献：
  名称：

  1,2-二氢吡啶-3,5-二羧酸乙酯的合成与性能

  摘要：

  DOI：

  10.1007/bf00513437
• 作为产物：
  描述：

  3-氨基巴豆酸乙酯 以 乙醇 为溶剂， 生成 1,2,6-trimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Dihydropyridines as inhibitors of capacitative calcium entry in leukemic HL-60 cells

  摘要：

  A series of 1,4-dihydropyridines (DHPs) were investigated as inhibitors of capacitative calcium influx through store-operated calcium (SOC) channels. Such channels activate after ATP-elicited release of inositol trisphosphate (IP3)-sensitive calcium stores in leukemia HL-60 cells. The most potent DHPs were those containing a 4-phenyl group with an electron-withdrawing substituent, such as m- or p-nitro- or in-trifluoromethyl (IC50 values: 3-6 muM). Benzyl esters, corresponding to the usual ethyl/methyl esters of the DHPs developed as L-type calcium channel blockers, retained potency at SOC channels, as did N-substituted DHPs. N-Methylation reduced by orders of magnitude the potency at L-type channels resulting in DHPs nearly equipotent at SOC and L-type channels. DHPs with N-ethyl, N-allyl, and N-propargyl groups also had similar potencies at SOC and L-type channels. Replacement of the usual 6-methyl group of DHPs with larger groups, such as cyclobutyl or phenyl, eliminated activity at the SOC channels; such DHPs instead elicited formation of inositol phosphates and release of IP3-sensitive calcium stores. Other DHPs also caused a release of calcium stores, but usually at significantly higher concentrations than those required for the inhibition of capacitative calcium influx. Certain DHPs appeared to cause an incomplete blockade of SOC channel-dependent elevations of calcium, suggesting the presence of more than one class of such channels in HL-60 cells. N-Methylnitrendipine (IC50 2.6 muM, MRS 1844) and N-propargylnifrendipine (IC50 1.7 muM, MRS 1845) represent possible lead compounds for the development of selective SOC channel inhibitors. Published by Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(02)01488-0

文献信息

• Novel Syntheses of Heterocycles with N-(1-Haloalkyl)azinium Halides. Part V. Preparation of N-Substituted 1,4-Dihydropyridines
  作者：Jean-Jacques Vanden Eynde、Annie Mayence、André Maquestiau、Ernst Anders

  DOI：10.1080/00397919208021145

  日期：1992.12

  Abstract Thirty N-substituted Hantzsch 1,4-dihydropyridines were prepared under mild and neutral conditions from N-substituted enaminocarbonyl derivatives and aldehydes activated under the form of N-(1-chloroalkyl)pyridinium chlorides by means of thionyl chloride and pyridine. The scope of the method is discussed.

  摘要 在温和和中性条件下，以N-(1-氯烷基)吡啶氯化物形式活化的N-取代烯氨基羰基衍生物和醛，通过亚硫酰氯和吡啶制备了30个N-取代Hantzsch 1,4-二氢吡啶。讨论了该方法的范围。
• MUTSENIETSE, D. X.;LUSIS, V. K.;DUBUR, G. YA., XIMIYA GETEROTSIKL. SOEDIN., 1982, N 9, 1225-1228
  作者：MUTSENIETSE, D. X.、LUSIS, V. K.、DUBUR, G. YA.

  DOI：——

  日期：——
• Dihydropyridines as inhibitors of capacitative calcium entry in leukemic HL-60 cells
  作者：Jacquie L Harper、Carol S Camerini-Otero、An-Hu Li、Soon-Ai Kim、Kenneth A Jacobson、John W Daly

  DOI：10.1016/s0006-2952(02)01488-0

  日期：2003.2

  A series of 1,4-dihydropyridines (DHPs) were investigated as inhibitors of capacitative calcium influx through store-operated calcium (SOC) channels. Such channels activate after ATP-elicited release of inositol trisphosphate (IP3)-sensitive calcium stores in leukemia HL-60 cells. The most potent DHPs were those containing a 4-phenyl group with an electron-withdrawing substituent, such as m- or p-nitro- or in-trifluoromethyl (IC50 values: 3-6 muM). Benzyl esters, corresponding to the usual ethyl/methyl esters of the DHPs developed as L-type calcium channel blockers, retained potency at SOC channels, as did N-substituted DHPs. N-Methylation reduced by orders of magnitude the potency at L-type channels resulting in DHPs nearly equipotent at SOC and L-type channels. DHPs with N-ethyl, N-allyl, and N-propargyl groups also had similar potencies at SOC and L-type channels. Replacement of the usual 6-methyl group of DHPs with larger groups, such as cyclobutyl or phenyl, eliminated activity at the SOC channels; such DHPs instead elicited formation of inositol phosphates and release of IP3-sensitive calcium stores. Other DHPs also caused a release of calcium stores, but usually at significantly higher concentrations than those required for the inhibition of capacitative calcium influx. Certain DHPs appeared to cause an incomplete blockade of SOC channel-dependent elevations of calcium, suggesting the presence of more than one class of such channels in HL-60 cells. N-Methylnitrendipine (IC50 2.6 muM, MRS 1844) and N-propargylnifrendipine (IC50 1.7 muM, MRS 1845) represent possible lead compounds for the development of selective SOC channel inhibitors. Published by Elsevier Science Inc.
• Synthesis and properties of ethyl esters of some 1,2-dihydropyridine-3,5-dicarboxylic acids
  作者：D. Kh. Mutsenietse、V. K. Lusis、G. Ya. Dubur

  DOI：10.1007/bf00513437

  日期：1982.9