4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-2-(4-hydroxybutoxy)-methyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine | 101411-59-0

• 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
• 英文名称: 4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-2-(4-hydroxybutoxy)-methyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine
• 英文别名: 4-{[4-(2,3-Dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-1-hydroxybutane；3-O-ethyl 5-O-methyl 4-(2,3-dichlorophenyl)-2-(4-hydroxybutoxymethyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 101411-59-0
• 化学式: C₂₂H₂₇Cl₂NO₆
• 分子量: 472.365
• InChiKey: FEWULSJYWSWEIB-UHFFFAOYSA-N

物化性质

• 沸点：
  571.7±50.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 4-<<4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl>methoxy>-2-butynoate 在 Lindlar's catalyst lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 3.17h， 生成 4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-2-(4-hydroxybutoxy)-methyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine
  参考文献：
  名称：

  Long-acting dihydropyridine calcium antagonists. 7. Compounds containing unsaturation in the 2-substituent on the 1,4-dihydropyridine ring

  摘要：

  To evaluate the effect of introducing unsaturation into the 2-substituent of 1,4-dihydropyridines related to amlodipine (1), a number of alkene and alkyne analogues were prepared and their calcium antagonist activity was assessed. For several series of compounds, in vitro potency increased in the order alkane < alkene < alkyne. This trend may either reflect decreasing entropy loss on binding to the DHP receptor or be a consequence of a favourable pi-interaction with the DHP receptor.

  DOI：

  10.1016/0223-5234(91)90197-u

文献信息

• Antihypertensive 2-hydroxyalkoxyalkyl dihydropyridines
  申请人：Pfizer Inc.

  公开号：US04654353A1

  公开（公告）日：1987-03-31

  Compounds of the formula: ##STR1## where R is an optionally substituted aryl or heteroaryl group; R.sup.1 and R.sup.2 are each independently C.sub.1 -C.sub.4 alkyl or 2-methoxyethyl; and Y is --(CH.sub.2).sub.n -- where n is 2, 3 or 4, --CH.sub.2 CH(CH.sub.3)-- or --Ch.sub.2 C(CH.sub.3).sub.2 --; and their pharmaceutically acceptable salts. The compounds have utility as anti-ischaemic and antihypertensive agents and as synthetic intermediates to other dihydropyridine calcium antagonists.

  式为：##STR1## 其中 R 是可选择取代的芳基或杂环芳基；R.sup.1 和 R.sup.2 分别独立地为 C.sub.1 -C.sub.4 烷基或 2-甲氧乙基；Y 为 --(CH.sub.2).sub.n --，其中 n 为 2、3 或 4，--CH.sub.2 CH(CH.sub.3)-- 或 --Ch.sub.2 C(CH.sub.3).sub.2 --；以及它们的药用可接受盐。这些化合物可用作抗缺血和降压药物，以及作为其他二氢吡啶钙拮抗剂的合成中间体。
• Dihydropyridines
  申请人：Pfizer Limited

  公开号：EP0161917A2

  公开（公告）日：1985-11-21

  Compounds of the formula: where R is an optionally substituted aryl or heteroaryl group; R1 and R are each independently C1-C4 alkyl or 2-methoxyethyl; and Y is -(CH2)n- where n is 2, 3 or 4, -CH2CH(CH3)-or -CH2C(CH3)2-; and their pharmaceutically acceptable salts. The compounds have utility as anti-ischaemic and antihypertensive agents and as synthetic intermediates to other dihydropyridine calcium antagonists.

  式中的化合物： 其中 R 是任选取代的芳基或杂芳基； R1和R各自独立地为C1-C4烷基或2-甲氧基乙基；Y为-(CH2)n-（其中n为2、3或4）、-CH2CH(CH3)-或-CH2C(CH3)2-；及其药学上可接受的盐类。 这些化合物可用作抗缺血和抗高血压药物，以及其他二氢吡啶类钙拮抗剂的合成中间体。
• US4654353A
  申请人：——

  公开号：US4654353A

  公开（公告）日：1987-03-31
• Long-acting dihydropyridine calcium antagonists. 7. Compounds containing unsaturation in the 2-substituent on the 1,4-dihydropyridine ring
  作者：D Alker、PE Cross

  DOI：10.1016/0223-5234(91)90197-u

  日期：1991.9

  To evaluate the effect of introducing unsaturation into the 2-substituent of 1,4-dihydropyridines related to amlodipine (1), a number of alkene and alkyne analogues were prepared and their calcium antagonist activity was assessed. For several series of compounds, in vitro potency increased in the order alkane < alkene < alkyne. This trend may either reflect decreasing entropy loss on binding to the DHP receptor or be a consequence of a favourable pi-interaction with the DHP receptor.