methyl 5-<2-<4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidyl>acetyl>-2-hydroxybenzoate | 74971-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-<2-<4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidyl>acetyl>-2-hydroxybenzoate
• 英文别名: Methyl 2-hydroxy-5-[4-(2-oxo-1-benzimidazolinyl)piperidinoacetyl]benzoate；methyl 2-hydroxy-5-[2-[4-(2-oxo-3H-benzimidazol-1-yl)piperidin-1-yl]acetyl]benzoate
• CAS: 74971-65-6
• 化学式: C₂₂H₂₃N₃O₅
• 分子量: 409.442
• InChiKey: LOURUUHGGNNGGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  99.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-<2-<4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidyl>acetyl>-2-hydroxybenzoate 、 硼氢化钠 、 、 碳酸氢钠 、 盐酸 在 ice methanol 、 二氯甲烷 、 水 、 magnesium sulfate 、 乙醚 、 甲醇 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 0.92h， 以leaving a residue of 11.3 g的产率得到methyl 2-hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)piperidino]ethyl]benzoate hydrochloride
  参考文献：
  名称：

  2-Hydro

  摘要：

  制备了2-羟基-5-[1-羟基-2-[4-(2-氧代-1-苯并咪唑啉基)哌啶基]乙基]苯甲酸的衍生物，这些衍生物对阻断α和β肾上腺素受体具有作用。此外，这些化合物对于其解痉和降压活性也是有用的。

  公开号：

  US04200755A1
• 作为产物：
  描述：

  5-乙酰水杨酸甲酯 在 溴 、 三乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 methyl 5-<2-<4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidyl>acetyl>-2-hydroxybenzoate
  参考文献：
  名称：

  Salicylamide derivatives related to medroxalol with .alpha.- and .beta.-adrenergic antagonist and antihypertensive activity

  摘要：

  Analogues of medroxalol (1) were prepared in which the carboxamide function, the phenolic hydroxy group, and the aralkylamine side chain were modified. N-alkyl-substituted amide analogues of 1 showed diminishing beta-blocking activity with increasing steric bulk of the alkyl group. This allowed the conclusion that deactivation of the phenolic hydroxy group of 1 by the carbonyl group of the amide function is responsible for the beta-adrenergic antagonistic properties of 1. This conclusion was strengthened by the finding that the phenolic O-methyl analogue 5-[2-[[3-(1,3-benzodioxol-5-yl)-1-methylpropyl]amino]-1hydroxyethyl]-2-methoxybenzamide (13) was found to have enhanced beta-adrenergic blocking activity. The finding that 13 also had decreased alpha-blocking activity compared to 1 indicated that the phenolic hydroxy group of 1 enhances alpha-adrenergic antagonism. The finding that 1 and 13 showed such a large difference in relative alpha- to beta-blocking potency while exhibiting approximately equal antihypertensive activity in spontaneously hypertensive rats was surprising. In indicated that pharmacologic properties other than alpha- and beta-adrenergic blockade may contribute to the antihypertensive activity of medroxalol. One of the analogues in which the aralkylamine side chain of 1 was replaced by a fragment of a known alpha-adrenergic receptor blocker, 2-hydroxy-5-[1-hydroxy-2-[4-(2-methylphenyl)-1-piperazinyl]ethyl]benzamide (22), showed an interesting pharmacologic profile of potential therapeutic usefulness.

  DOI：

  10.1021/jm00135a017

文献信息

• US4200755A
  申请人：——

  公开号：US4200755A

  公开（公告）日：1980-04-29
• Salicylamide derivatives related to medroxalol with .alpha.- and .beta.-adrenergic antagonist and antihypertensive activity
  作者：J. Martin Grisar、George P. Claxton、Thomas M. Bare、Richard C. Dage、Hsien C. Cheng、James K. Woodward

  DOI：10.1021/jm00135a017

  日期：1981.3

  Analogues of medroxalol (1) were prepared in which the carboxamide function, the phenolic hydroxy group, and the aralkylamine side chain were modified. N-alkyl-substituted amide analogues of 1 showed diminishing beta-blocking activity with increasing steric bulk of the alkyl group. This allowed the conclusion that deactivation of the phenolic hydroxy group of 1 by the carbonyl group of the amide function is responsible for the beta-adrenergic antagonistic properties of 1. This conclusion was strengthened by the finding that the phenolic O-methyl analogue 5-[2-[[3-(1,3-benzodioxol-5-yl)-1-methylpropyl]amino]-1hydroxyethyl]-2-methoxybenzamide (13) was found to have enhanced beta-adrenergic blocking activity. The finding that 13 also had decreased alpha-blocking activity compared to 1 indicated that the phenolic hydroxy group of 1 enhances alpha-adrenergic antagonism. The finding that 1 and 13 showed such a large difference in relative alpha- to beta-blocking potency while exhibiting approximately equal antihypertensive activity in spontaneously hypertensive rats was surprising. In indicated that pharmacologic properties other than alpha- and beta-adrenergic blockade may contribute to the antihypertensive activity of medroxalol. One of the analogues in which the aralkylamine side chain of 1 was replaced by a fragment of a known alpha-adrenergic receptor blocker, 2-hydroxy-5-[1-hydroxy-2-[4-(2-methylphenyl)-1-piperazinyl]ethyl]benzamide (22), showed an interesting pharmacologic profile of potential therapeutic usefulness.
• 2-Hydro
  申请人：Richardson-Merrell Inc.

  公开号：US04200755A1

  公开（公告）日：1980-04-29

  Derivatives of 2-hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)piperidino]ethyl]ben zoic acid are prepared which are useful for their blocking action on .alpha. and .beta.-adrenergic receptors. In addition, these compounds are useful for their spasmolytic and anti-hypertensive activity.

  制备了2-羟基-5-[1-羟基-2-[4-(2-氧代-1-苯并咪唑啉基)哌啶基]乙基]苯甲酸的衍生物，这些衍生物对阻断α和β肾上腺素受体具有作用。此外，这些化合物对于其解痉和降压活性也是有用的。