methyl (2Z)-4-chloro-2-[(3-nitrophenyl)methylidene]-3-oxobutanoate | 107813-00-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (2Z)-4-chloro-2-[(3-nitrophenyl)methylidene]-3-oxobutanoate
• CAS: 107813-00-3
• 化学式: C₁₂H₁₀ClNO₅
• 分子量: 283.668
• InChiKey: YHSCXDGBJKFPLP-POHAHGRESA-N

物化性质

• 沸点：
  409.7±45.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2Z)-4-chloro-2-[(3-nitrophenyl)methylidene]-3-oxobutanoate 以 异丙醇 、 乙腈 为溶剂， 反应 44.0h， 生成 Dimethyl 2-(imidazol-1-ylmethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  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
• 作为产物：
  描述：

  4-氯乙酰乙酸甲酯 、 间硝基苯甲醛 在 溶剂黄146 、 苄胺 作用下， 以 异丙醇 为溶剂， 反应 20.0h， 生成 methyl (2Z)-4-chloro-2-[(3-nitrophenyl)methylidene]-3-oxobutanoate
  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

• N-aryl-2-hydroxy-1,2,3,4-tetrahydropyridines and N-aryl-2-chloromethylene-1,2,3,4-tetrahydropyridines — successive intermediates in the Hantzsch synthesis of 1,4-dihydropyridines
  作者：B. Chekavichus、Yu. Popelis、E. Shebenina、A. Sausin'sh、R. Verkhe、G. Duburs

  DOI：10.1007/bf02253029

  日期：1997.7
• Formation of 1-aryl-2-chloromethylene-1,2,3,4-tetrahydropyridines and isomerization to 1,4-dihydropyridines
  作者：B. S. Chekavichus、I. S. Birgele、A. �. Sausin'sh、G. Ya. Dubur

  DOI：10.1007/bf00474506

  日期：1992.7