O3-乙基O5-甲基2-(咪唑-1-基甲基)-6-甲基-4-(3-硝基苯基)-1,4-二氢吡啶-3,5-二羧酸酯 | 103417-69-2

• 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
• 中文名称: O3-乙基O5-甲基2-(咪唑-1-基甲基)-6-甲基-4-(3-硝基苯基)-1,4-二氢吡啶-3,5-二羧酸酯
• 英文名称: WY 27569
• 英文别名: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2-(1H-imidazol-1-ylmethyl)-6-methyl-4-(3-nitrophenyl)-, 3-ethyl 5-methyl ester；3-O-ethyl 5-O-methyl 2-(imidazol-1-ylmethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 103417-69-2
• 化学式: C₂₁H₂₂N₄O₆
• 分子量: 426.429
• InChiKey: BFLKGKGRZKABHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  O3-乙基O5-甲基2-(咪唑-1-基甲基)-6-甲基-4-(3-硝基苯基)-1,4-二氢吡啶-3,5-二羧酸酯 、 盐酸 生成 3,5-吡啶二羧酸,1,4-二氢-2-(1H-咪唑-1-基甲基)-6-甲基-4-(3-硝基苯基)-,3-乙基5-甲基酯,盐酸(1:1)
  参考文献：
  名称：

  BRADLEY, GERALD;PHILIP, CEOFFREY;CARR, RAYMOND;OPAIKO, ALBERT;YARWOOD, RI+

  摘要：

  DOI：
• 作为产物：
  描述：

  4-Chloro-2-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester 以 异丙醇 、 乙腈 为溶剂， 反应 44.0h， 生成 O3-乙基O5-甲基2-(咪唑-1-基甲基)-6-甲基-4-(3-硝基苯基)-1,4-二氢吡啶-3,5-二羧酸酯
  参考文献：
  名称：

  Design of an antithrombotic-antihypertensive agent (Wy 27569). Synthesis and evaluation of a series of 2-heteroaryl substituted dihydropyridines

  摘要：

  An approach to the design of potential combined antithrombotic-antihypertensive agents is described. A series of 1,4-dihydropyridines bearing a 1H-imidazol-1-yl or pyrid-3-yl substituted side chain in the 2-position were synthesized and tested for antihypertensive activity in spontaneously hypertensive rats and for inhibition of TXA2 synthetase in rabbit platelets, in vitro. 1,4-Dihydro-2-(1H-imidazol-1-ylmethyl)-6-methyl- 4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 3-ethyl 5-methyl diester (1) was shown to be similar in potency to nitrendipine as an antihypertensive agent. Compound 1 inhibited TXA2 synthetase in rabbit and human platelets in vitro and reduced plasma TXB2 levels in rats at antihypertensive dose levels. The reductions in thromboxane production observed in vivo and in vitro were accompanied by enhanced levels of 6-KPGF1 alpha, reflecting diversion of the arachidonic acid cascade toward prostacyclin synthesis.

  DOI：

  10.1021/jm00164a028

文献信息

• BRADLEY, GERALD;PHILIP, CEOFFREY;CARR, RAYMOND;OPAIKO, ALBERT;YARWOOD, RI+
  作者：BRADLEY, GERALD、PHILIP, CEOFFREY、CARR, RAYMOND、OPAIKO, ALBERT、YARWOOD, RI+

  DOI：——

  日期：——
• Design of an antithrombotic-antihypertensive agent (Wy 27569). Synthesis and evaluation of a series of 2-heteroaryl substituted dihydropyridines
  作者：John L. Archibald、Gerald Bradley、Albert Opalko、Terence J. Ward、Janet C. White、Christine Ennis、Nicholas B. Shepperson

  DOI：10.1021/jm00164a028

  日期：1990.2

  An approach to the design of potential combined antithrombotic-antihypertensive agents is described. A series of 1,4-dihydropyridines bearing a 1H-imidazol-1-yl or pyrid-3-yl substituted side chain in the 2-position were synthesized and tested for antihypertensive activity in spontaneously hypertensive rats and for inhibition of TXA2 synthetase in rabbit platelets, in vitro. 1,4-Dihydro-2-(1H-imidazol-1-ylmethyl)-6-methyl- 4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 3-ethyl 5-methyl diester (1) was shown to be similar in potency to nitrendipine as an antihypertensive agent. Compound 1 inhibited TXA2 synthetase in rabbit and human platelets in vitro and reduced plasma TXB2 levels in rats at antihypertensive dose levels. The reductions in thromboxane production observed in vivo and in vitro were accompanied by enhanced levels of 6-KPGF1 alpha, reflecting diversion of the arachidonic acid cascade toward prostacyclin synthesis.