2-氯甲基-1,4-二氢-6-甲基-4-(3-硝基苯基)-3,5-吡啶二甲酸甲酯 | 105435-13-0

• 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: 2-氯甲基-1,4-二氢-6-甲基-4-(3-硝基苯基)-3,5-吡啶二甲酸甲酯
• 英文名称: methyl 2-chloromethyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
• 英文别名: Dimethyl 2-(chloromethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate；dimethyl 2-(chloromethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 105435-13-0
• 化学式: C₁₇H₁₇ClN₂O₆
• 分子量: 380.785
• InChiKey: UAIULPGUBUBSGH-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C(Solv: methanol (67-56-1))
• 沸点：
  503.5±50.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  咪唑 、 2-氯甲基-1,4-二氢-6-甲基-4-(3-硝基苯基)-3,5-吡啶二甲酸甲酯 以 乙腈 为溶剂， 反应 20.0h， 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 在 溶剂黄146 、 苄胺 作用下， 以 异丙醇 为溶剂， 反应 44.0h， 生成 2-氯甲基-1,4-二氢-6-甲基-4-(3-硝基苯基)-3,5-吡啶二甲酸甲酯
  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

• 1,4-Dihydropyridine dicarboxylic acid derivatives
  申请人：ZAMBON GROUP S.p.A.

  公开号：EP0352863A3

  公开（公告）日：1990-08-22

  Compounds of formula (wherein Ar, R, R₁, R₂, R₃, R₄, R₅, m and n have the meanings given in the description), their preparation and pharmaceutical compositions containing them.The compounds of formula I are active on the cardiovascular system as antivasospastics, antiangina agents, antihyper­tensives and vasodilators.

  具有以下式中的化合物（其中Ar，R，R₁，R₂，R₃，R₄，R₅，m和n的含义如描述中所述），它们的制备以及含有它们的药物组合物。式I中的化合物对心血管系统具有活性，可作为抗血管痉挛剂、抗心绞痛药物、降压药和血管扩张剂。
• Compounds active on the cardiovascular system
  申请人：Zambon Group S.p.A.

  公开号：US05468746A1

  公开（公告）日：1995-11-21

  Compounds of the formula ##STR1## (wherein Ar, R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, m and n have the meanings given in the description), their preparation and pharmaceutical compositions containing them. The compounds of formula I are active on the cardiovascular system as antivasospastics, antiangina agents, antihypertensives and vasodilators.

  公式##STR1##的化合物（其中Ar、R、R.sub.1、R.sub.2、R.sub.3、R.sub.4、R.sub.5、m和n的含义如描述中所给），它们的制备以及含有它们的药物组合物。公式I的化合物在心血管系统上具有抗痉挛、抗心绞痛、降压和扩血管的活性。
• 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
• Cupka, Pavol; Svetlik, Jan, Synthetic Communications, 1986, vol. 16, # 5, p. 529 - 534
  作者：Cupka, Pavol、Svetlik, Jan

  DOI：——

  日期：——
• CUPKA, P.;SVETLIK, J., SYNTH. COMMUN., 1986, 16, N 5, 529-534
  作者：CUPKA, P.、SVETLIK, J.

  DOI：——

  日期：——