4-Chloro-2-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester | 121223-45-8

• 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: 4-Chloro-2-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester
• 英文别名: ethyl (2Z)-4-chloro-2-[(3-nitrophenyl)methylidene]-3-oxobutanoate
• CAS: 121223-45-8
• 化学式: C₁₃H₁₂ClNO₅
• 分子量: 297.695
• InChiKey: ZTQJSJLZARPEBW-XFFZJAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  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
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 、 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 4-Chloro-2-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester
  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

• 2-(heteroalkyl)-1,4-dihydropyridines, process for their preparations and pharmaceutical compositions containing them
  申请人：BOEHRINGER MANNHEIM ITALIA S.P.A.

  公开号：EP0212340B1

  公开（公告）日：1993-10-27
• PHARMACEUTICALLY ACTIVE 2-THIOMETHYL-SUBSTITUTED-1,4-DIHYDROPYRIDINES
  申请人：BOEHRINGER BIOCHEMIA ROBIN S.p.A.

  公开号：EP0233228A1

  公开（公告）日：1987-08-26
• US4839348A
  申请人：——

  公开号：US4839348A

  公开（公告）日：1989-06-13
• US5021436A
  申请人：——

  公开号：US5021436A

  公开（公告）日：1991-06-04
• US4999362A
  申请人：——

  公开号：US4999362A

  公开（公告）日：1991-03-12