(+/-)-methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(2-azido-3-nitrophenyl)pyridine-3-carboxylate | 223669-42-9

• 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: (+/-)-methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(2-azido-3-nitrophenyl)pyridine-3-carboxylate
• 英文别名: methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(2-azido-3-nitrophenyl)-pyridine-3-carboxylate；Methyl 4-(2-azido-3-nitrophenyl)-2,6-dimethyl-5-nitro-1,4-dihydropyridine-3-carboxylate
• CAS: 223669-42-9
• 化学式: C₁₅H₁₄N₆O₆
• 分子量: 374.313
• InChiKey: BUPODIHSWBEBPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (+/-)-methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(2-azido-3-nitrophenyl)pyridine-3-carboxylate 以 四氢呋喃 为溶剂， 反应 24.0h， 以40%的产率得到(+/-)-methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(benzofurazan-4(7)-yl)pyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis and Voltage-Clamp Studies of Methyl 1,4-Dihydro-2,6-dimethyl-5-nitro-4-(benzofurazanyl)pyridine-3-carboxylate Racemates and Enantiomers and of Their Benzofuroxanyl Analogues

  摘要：

  Racemic methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(benzofurazanyl)pyridine-3-carboxylates(+/-)-10 and (+/-)-11 and their benzofuroxanyl analogues (+/-)-12 and (+/-)-13 were prepared using a modified Hantzsch reaction that involved the condensation of nitroacetone with methyl 3-aminocrotonate and the appropriate aldehydes. The racemic mixtures were resolved into the corresponding enantiomers. Whole-cell voltage-clamp studies on L-type Ca2+ channels expressed in a rat insulinoma cell line (RINm5F) showed that all the dextrorotatory antipodes were effective agonists of L-type Ca2+ currents, while the levorotatory ones were weak Ca2+ entry blockers. The (+)-enantiomer of benzofurazan-5'-yl derivative 11 demonstrated unusual activity in that, in addition to producing a potentiation of L-type currents, it interfered with the voltage-dependent gating of L-type channels by producing a net delay of their activation at low voltages. This compound represents an interesting tool to probe L-type Ca2+ channel structure and function.

  DOI：

  10.1021/jm980623b
• 作为产物：
  描述：

  2-叠氮基-1-甲基-3-硝基苯 在 chromium(VI) oxide 、 盐酸 、 硫酸 、 溶剂黄146 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 8.75h， 生成 (+/-)-methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(2-azido-3-nitrophenyl)pyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis and Voltage-Clamp Studies of Methyl 1,4-Dihydro-2,6-dimethyl-5-nitro-4-(benzofurazanyl)pyridine-3-carboxylate Racemates and Enantiomers and of Their Benzofuroxanyl Analogues

  摘要：

  Racemic methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(benzofurazanyl)pyridine-3-carboxylates(+/-)-10 and (+/-)-11 and their benzofuroxanyl analogues (+/-)-12 and (+/-)-13 were prepared using a modified Hantzsch reaction that involved the condensation of nitroacetone with methyl 3-aminocrotonate and the appropriate aldehydes. The racemic mixtures were resolved into the corresponding enantiomers. Whole-cell voltage-clamp studies on L-type Ca2+ channels expressed in a rat insulinoma cell line (RINm5F) showed that all the dextrorotatory antipodes were effective agonists of L-type Ca2+ currents, while the levorotatory ones were weak Ca2+ entry blockers. The (+)-enantiomer of benzofurazan-5'-yl derivative 11 demonstrated unusual activity in that, in addition to producing a potentiation of L-type currents, it interfered with the voltage-dependent gating of L-type channels by producing a net delay of their activation at low voltages. This compound represents an interesting tool to probe L-type Ca2+ channel structure and function.

  DOI：

  10.1021/jm980623b

文献信息

• Thermolysis of 4-(2-azido-3-nitrophenyl)-1,4-dihydropyridines as source of β-carboline derivatives and some related compounds
  作者：Sonja Visentin、Giuseppe Ermondi、Donatella Boschi、Giorgio Grosa、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/s0040-4039(01)00777-8

  日期：2001.7

  Thermolysis in refluxing xylene of 4-(2-azido-3-nitrophenyl)-1,4-dihydropyridines was investigated. β-Carboline derivatives and related compounds were obtained in various yields, according to the nature of the substituents in the 1,4-dihydropyridine ring.

  研究了4-（2-叠氮基-3-硝基苯基）-1,4-二氢吡啶在回流二甲苯中的热解。根据1，4-二氢吡啶环中取代基的性质，可以各种产率获得β-咔啉衍生物和相关化合物。
• Synthesis and Voltage-Clamp Studies of Methyl 1,4-Dihydro-2,6-dimethyl-5-nitro-4-(benzofurazanyl)pyridine-3-carboxylate Racemates and Enantiomers and of Their Benzofuroxanyl Analogues
  作者：Sonja Visentin、Pascale Amiel、Roberta Fruttero、Donatella Boschi、Christian Roussel、Laura Giusta、Emilio Carbone、Alberto Gasco

  DOI：10.1021/jm980623b

  日期：1999.4.22

  Racemic methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(benzofurazanyl)pyridine-3-carboxylates(+/-)-10 and (+/-)-11 and their benzofuroxanyl analogues (+/-)-12 and (+/-)-13 were prepared using a modified Hantzsch reaction that involved the condensation of nitroacetone with methyl 3-aminocrotonate and the appropriate aldehydes. The racemic mixtures were resolved into the corresponding enantiomers. Whole-cell voltage-clamp studies on L-type Ca2+ channels expressed in a rat insulinoma cell line (RINm5F) showed that all the dextrorotatory antipodes were effective agonists of L-type Ca2+ currents, while the levorotatory ones were weak Ca2+ entry blockers. The (+)-enantiomer of benzofurazan-5'-yl derivative 11 demonstrated unusual activity in that, in addition to producing a potentiation of L-type currents, it interfered with the voltage-dependent gating of L-type channels by producing a net delay of their activation at low voltages. This compound represents an interesting tool to probe L-type Ca2+ channel structure and function.