2,6-dimethyl-3-methoxycarbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 4-methoxybenzyl ester | 61311-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-dimethyl-3-methoxycarbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 4-methoxybenzyl ester
• 英文别名: 2,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridin-5-carbonsaeure-(4-methoxybenzyl)ester；5-O-[(4-methoxyphenyl)methyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 61311-88-4
• 化学式: C₂₄H₂₄N₂O₇
• 分子量: 452.464
• InChiKey: WGBGXHMGSAULRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 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：
  120
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-3-methoxycarbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 4-methoxybenzyl ester 以 乙醇 为溶剂， 以Analogously to Example 1 heating a solution of 75 mmols of 3'-nitrobenzylideneacetoacetic acid methyl ester and 75 mmols of β-aminocrotonic acid 4-methoxybenzyl ester in 120 ml of ethanol gave 2,6-dimethyl-3-methoxycarbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 4-methoxybenzyl ester of melting point 136° C (from ethanol)的产率得到
  参考文献：
  名称：

  1,4-Dihydropyridines

  摘要：

  在1,4-二氢吡啶中，其5位上特征为羧基(芳基氧基)基团，4位上为芳基基团，3位上为烷酰基或羧基烷基基团，而在1,2和6位上进一步可选择性地取代，这些化合物是冠状动脉扩张、解痉和降压剂。这些化合物的代表性实施例包括2,6-二甲基-3-羧甲氧基-4-(2-硝基苯基)-5-羧苯甲酰基-1,4-二氢吡啶，通过β-二羰基化合物的反应生成物(可由相应的β-二羰基化合物和醛在原位生成)和恩氨基羧酸酯的反应生成物(也可由β-二羰基化合物和胺在原位生成)制备而成。

  公开号：

  US04044141A1
• 作为产物：
  描述：

  (4-methoxyphenyl)methyl 3-aminocrotonate 以 乙醇 为溶剂， 以75%的产率得到2,6-dimethyl-3-methoxycarbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 4-methoxybenzyl ester
  参考文献：
  名称：

  1,4-Dihydropyridines

  摘要：

  在1,4-二氢吡啶中，其5位上具有碳基(芳基氧基)基团，4位上具有芳基基团，3位上具有烷酰基或羰基烷基基团，并在1、2和6位上进一步可选地被取代。这些化合物是冠状动脉扩张、解痉和降压剂。其中2,6-二甲基-3-羧甲氧基-4-(2-硝基苯基)-5-羧基苯甲酰基-1,4-二氢吡啶是一种典型的实施例，可以通过将一个双羰基化合物的β-位产生的叶亚胺与一个烯丙氨基酸酯反应而制备出来，该叶亚胺可以在相应的β-二羰基化合物和醛的作用下现场生成，而烯丙氨基酸酯也可以在β-二羰基化合物和胺的作用下现场生成。

  公开号：

  US04044141A1

文献信息

• Antagonism of 4-substituted 1,4-dihydropyridine-3,5-dicarboxylates toward voltage-dependent L-type Ca2+ channels CaV1.3 and CaV1.2
  作者：Che-Chien Chang、Song Cao、Soosung Kang、Li Kai、Xinyong Tian、Prativa Pandey、Sara Fernandez Dunne、Chi-Hao Luan、D. James Surmeier、Richard B. Silverman

  DOI：10.1016/j.bmc.2010.03.038

  日期：2010.5

  L-type Ca2+ channels in mammalian brain neurons have either a Ca(V)1.2 or Ca(V)1.3 pore-forming subunit. Recently, it was shown that Ca(V)1.3 Ca2+ channels underlie autonomous pacemaking in adult dopaminergic neurons in the substantia nigra pars compacta, and this reliance renders them sensitive to toxins used to create animal models of Parkinson's disease. Antagonism of these channels with the dihydropyridine antihypertensive drug isradipine diminishes the reliance on Ca2+ and the sensitivity of these neurons to toxins, pointing to a potential neuroprotective strategy. However, for neuroprotection without an antihypertensive side effect, selective Ca(V)1.3 channel antagonists are required. In an attempt to identify potent and selective antagonists of Ca(V)1.3 channels, 124 dihydropyridines (4-substituted-1,4-dihydropyridine3,5-dicarboxylic diesters) were synthesized. The antagonism of heterologously expressed Ca(V)1.2 and Ca(V)1.3 channels was then tested using electrophysiological approaches and the FLIPR Calcium 4 assay. Despite the large diversity in substitution on the dihydropyridine scaffold, the most Ca(V)1.3 selectivity was only about twofold. These results support a highly similar dihydropyridine binding site at both Ca(V)1.2 and Ca(V)1.3 channels and suggests that other classes of compounds need to be identified for Ca(V)1.3 selectivity. (c) 2010 Elsevier Ltd. All rights reserved.
• US4044141A
  申请人：——

  公开号：US4044141A

  公开（公告）日：1977-08-23
• 1,4-Dihydropyridines
  申请人：Bayer Aktiengesellschaft

  公开号：US04044141A1

  公开（公告）日：1977-08-23

  1,4-Dihydropyridines characterized by a carbo(arylalkoxy) group in the 5-position, an aryl group in the 4-position and a alkanoyl or carbalkoxy group in the 3-position and further optionally substituted in the 1,2 and 6-positions are coronary dilating, spasmolytic and hypotensive agents. The compounds, of which 2,6-dimethyl-3-carbomethoxy-4-(2-nitrophenyl)-5-carbobenzoxy-1,4-dihydropy ridine is a representative embodiment, are prepared through the reaction of an ylidene-.beta.-dicarbonyl compound, which may be generated in situ from the corresponding .beta.-dicarbonyl compound and an aldehyde, and an enaminocarboxylic acid ester, which may also be generated in situ from a .beta.-dicarbonyl compound and an amine.

  在1,4-二氢吡啶中，其5位上具有碳基(芳基氧基)基团，4位上具有芳基基团，3位上具有烷酰基或羰基烷基基团，并在1、2和6位上进一步可选地被取代。这些化合物是冠状动脉扩张、解痉和降压剂。其中2,6-二甲基-3-羧甲氧基-4-(2-硝基苯基)-5-羧基苯甲酰基-1,4-二氢吡啶是一种典型的实施例，可以通过将一个双羰基化合物的β-位产生的叶亚胺与一个烯丙氨基酸酯反应而制备出来，该叶亚胺可以在相应的β-二羰基化合物和醛的作用下现场生成，而烯丙氨基酸酯也可以在β-二羰基化合物和胺的作用下现场生成。