4-(3-Methoxy-4-oxo-2-phenyl-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester | 853294-40-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4-(3-Methoxy-4-oxo-2-phenyl-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 4-(3-methoxy-4-oxo-2-phenylchromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 853294-40-3
• 化学式: C₂₇H₂₅NO₇
• 分子量: 475.498
• InChiKey: ZKVDDGLKKNAKKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(3-Methoxy-4-oxo-2-phenyl-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester 在 吡啶 、 pyridinium hydrobromide perbromide 作用下， 以 氯仿 为溶剂， 反应 1.83h， 生成 4-(3-Methoxy-4-oxo-2-phenyl-4H-chromen-8-yl)-2-methyl-5-oxo-1,4,5,7-tetrahydro-furo[3,4-b]pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  1,4-Dihydropyridine derivatives as calcium channel modulators: the role of 3-methoxy-flavone moiety

  摘要：

  It was earlier recognized that calcium antagonists, and in particular 1,4-dihydropyridines, exhibited distinct cardiovascular profiles. In addition two different splice variants of the L-type calcium channel were found in vascular and cardiac tissues. In this study, novel substituted 1,4-dihydropyridines with a 3-methoxy-flavone moiety were synthesized and structural modifications of the substituents in the dihydropyridine ring of nifedipine were carried out in order to find tissue specific compounds. The negative inotropic, chronotropic and vasorelaxant effects were investigated on guinea-pig left, right atria and aortic strips, respectively. The introduction of an heteroaromatic ring in 4-position of the 1,4-dihydropyridine nucleus led to compounds selective for cardiac tissues. Moreover, different residues in the 1,4-dihydropyridine ring could modulate the chronotropic versus inotropic activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.007
• 作为产物：
  描述：

  3-甲氧基-8-甲基-2-苯基色烯-4-酮 在 N-溴代丁二酰亚胺(NBS) 、 乌洛托品 、 氨 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 异丙醇 为溶剂， 反应 39.0h， 生成 4-(3-Methoxy-4-oxo-2-phenyl-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  1,4-Dihydropyridine derivatives as calcium channel modulators: the role of 3-methoxy-flavone moiety

  摘要：

  It was earlier recognized that calcium antagonists, and in particular 1,4-dihydropyridines, exhibited distinct cardiovascular profiles. In addition two different splice variants of the L-type calcium channel were found in vascular and cardiac tissues. In this study, novel substituted 1,4-dihydropyridines with a 3-methoxy-flavone moiety were synthesized and structural modifications of the substituents in the dihydropyridine ring of nifedipine were carried out in order to find tissue specific compounds. The negative inotropic, chronotropic and vasorelaxant effects were investigated on guinea-pig left, right atria and aortic strips, respectively. The introduction of an heteroaromatic ring in 4-position of the 1,4-dihydropyridine nucleus led to compounds selective for cardiac tissues. Moreover, different residues in the 1,4-dihydropyridine ring could modulate the chronotropic versus inotropic activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.007

文献信息

• 1,4-Dihydropyridine derivatives as calcium channel modulators: the role of 3-methoxy-flavone moiety
  作者：Roberta Budriesi、Alessandra Bisi、Pierfranco Ioan、Angela Rampa、Silvia Gobbi、Federica Belluti、Lorna Piazzi、Piero Valenti、Alberto Chiarini

  DOI：10.1016/j.bmc.2005.03.007

  日期：2005.5

  It was earlier recognized that calcium antagonists, and in particular 1,4-dihydropyridines, exhibited distinct cardiovascular profiles. In addition two different splice variants of the L-type calcium channel were found in vascular and cardiac tissues. In this study, novel substituted 1,4-dihydropyridines with a 3-methoxy-flavone moiety were synthesized and structural modifications of the substituents in the dihydropyridine ring of nifedipine were carried out in order to find tissue specific compounds. The negative inotropic, chronotropic and vasorelaxant effects were investigated on guinea-pig left, right atria and aortic strips, respectively. The introduction of an heteroaromatic ring in 4-position of the 1,4-dihydropyridine nucleus led to compounds selective for cardiac tissues. Moreover, different residues in the 1,4-dihydropyridine ring could modulate the chronotropic versus inotropic activity. (c) 2005 Elsevier Ltd. All rights reserved.