(+/-)-dimethylaminoethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate | 55985-22-3

• 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: (+/-)-dimethylaminoethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
• 英文别名: 5-O-[2-(dimethylamino)ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 55985-22-3
• 化学式: C₂₀H₂₅N₃O₆
• 分子量: 403.435
• InChiKey: SBFWAGOTYLZDPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,6-二甲基-5-甲氧羰基-4-(3-硝基苯基)-1,4-二氢吡啶-3-羧酸 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (+/-)-dimethylaminoethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  Permanently Charged Chiral 1,4-Dihydropyridines:  Molecular Probes of L-Type Calcium Channels. Synthesis and Pharmacological Characterization of Methyl (ω-Trimethylalkylammonium) 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5- pyridinedicarboxylate Iodide, Calcium Channel Antagonists

  摘要：

  We report the synthesis of the single enantiomers of permanently charged dihydropyridine derivatives (DHPs with alkyl linker lengths of two and eight carbon atoms) and their activities on cardiac and neuronal L-type calcium channels. Permanently charged chiral 1,4-dihydropyridines and methyl (omega-trimethylalkylammonium) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)- 3,5-pyridinedicarboxylate iodides were synthesized in high optical purities from (R)-(-) and (S)-(+)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-3-pyridinecarboxylic acid, obtained by resolution of racemic 1,4-dihvdro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)- 3-pyridinecarboxylic acid. Competition binding experiments with radioligand [H-3]-(+)-PN200-110 and the block of whole cell barium currents through L-type calcium channels in GH(4)C(1) cells Show that the compounds with the eight-carbon alkyl. linker optimally block the L-type Ca2+ channels, and that the S-enantiomer is more potent than the R-enantiomer.

  DOI：

  10.1021/jm000028l

文献信息

• Processes of manufacturing substituted-1,4-dihydropyridines, improved aqueous solutions thereof, and processes of manufacturing the solutions
  申请人：Jobdevairakkam Christopher N.

  公开号：US20080125595A1

  公开（公告）日：2008-05-29

  A process of preparing a stable parenteral solution of a 1,4-dihydropyridine salt, such as nicardipine hydrochloride, in an acidic aqueous medium. The presence of L-arginine in the solution enhances the solubility of the salt, which is poorly soluble in water. An aqueous, injectable isotonic solution at pH about 3.5-3.6 consists essentially of nicardipine hydrochloride, L-arginine, and a sugar alcohol. An improved single pot manufacturing process for obtaining unsymmetrical 1,4-dihydropyridines by using more than one mole equivalent of aldehyde with respect to the other reactants (amino crotonate and acetoacetate ester). The reaction can be conducted in a solvent present at 20 times the amount of any one component. A process for changing one polymorph of nicardipine hydrochloride (Form A) into another (Form B), and a separate process for the reverse (Form B into Form A).

  一种制备1,4-二氢吡啶盐（如盐酸尼卡地平）的稳定无菌溶液的工艺，该工艺在酸性水介质中进行。溶液中存在L-精氨酸，可增强盐的溶解度，而盐在水中溶解度较差。该无菌溶液为水溶性、注射用的等渗溶液，pH值约为3.5-3.6，主要由盐酸尼卡地平、L-精氨酸和糖醇组成。 一种改进的单锅制造工艺，用于通过使用超过其他反应物（氨基丙烯酸酯和乙酰乙酸酯）的摩尔当量的醛类来获得非对称的1,4-二氢吡啶。该反应可以在溶剂中进行，溶剂的量为任何一个组分的20倍。 一种将尼卡地平盐酸的一种多晶形式（A型）转变为另一种多晶形式（B型）的工艺，以及将B型转变为A型的单独工艺。
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