4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-2-(4-hydroxy-2-butynyloxy)-methyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine | 121590-49-6

• 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-hydroxy-2-butynyloxy)-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-hydroxybut-2-yne；3-O-ethyl 5-O-methyl 4-(2,3-dichlorophenyl)-2-(4-hydroxybut-2-ynoxymethyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 121590-49-6
• 化学式: C₂₂H₂₃Cl₂NO₆
• 分子量: 468.334
• InChiKey: NUDLAHZEIUHSHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-2-(4-hydroxy-2-butynyloxy)-methyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以61%的产率得到4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-2-(4-hydroxy-(2E)-butenyloxy)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
• 作为产物：
  描述：

  ethyl 4<<4-(2,3-dichlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridin-2-yl>methoxy>-2-butynoate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 以64%的产率得到4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-2-(4-hydroxy-2-butynyloxy)-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

• Dihydropyridine derivatives
  申请人：Pfizer Inc.

  公开号：US04957930A1

  公开（公告）日：1990-09-18

  Dihydropyridines having unsaturated side chains are disclosed. The compounds are useful anti-ischemic and antihypertensive agents.

  揭示了具有不饱和侧链的二氢吡啶类化合物。这些化合物是有用的抗缺血和降压药物。
• 1,4 Dihydropyridine derivatives, process for their preparation and their uses in pharmaceutical compositions
  申请人：Pfizer Limited

  公开号：EP0295769A2

  公开（公告）日：1988-12-21

  Dihydropyridine derivatives of the formula: where R is aryl or heteroaryl, R¹ and R² are each alkyl or methoxyethyl, X is O or S, Y is -CH=CH- or -C≡C-, and Z is -CHR⁵OH, -CONH₂, -CO₂R⁶ or -CH₂NR³R⁴, where R³ and R⁴ are H or alkyl or together form a 5- or 6-membered ring, R⁵ is H, alkyl or aryl, and R⁶ is H or alkyl, are anti-ischaemic and antihypertensive agents. All except compounds in which Y is -C≡C- ­and Z is -CO₂alkyl are novel.

  式中的二氢吡啶衍生物： 其中 R 是芳基或杂芳基，R¹ 和 R² 各自是烷基或甲氧基乙基，X 是 O 或 S，Y 是 -CH=CH- 或 -C≡C-，Z 是 -CHR⁵OH、-CONH₂、-CO₂R⁶ 或 -CH₂NR³R⁴、其中 R³ 和 R⁴ 是 H 或烷基或共同形成 5 或 6 元环，R⁵ 是 H、烷基或芳基，R⁶ 是 H 或烷基，这些化合物都是抗缺血和抗高血压药物。除 Y 为-C≡C-和 Z 为-CO₂烷基的化合物外，其他化合物均为新型化合物。
• US4957930A
  申请人：——

  公开号：US4957930A

  公开（公告）日：1990-09-18
• 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.