methyl 2-hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)piperidino]ethyl]benzoate hydrochloride | 74971-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)piperidino]ethyl]benzoate hydrochloride
• 英文别名: methyl 2-hydroxy-5-[1-hydroxy-2-[4-(2-oxo-3H-benzimidazol-1-yl)piperidin-1-yl]ethyl]benzoate;hydrochloride
• CAS: 74971-66-7
• 化学式: C₂₂H₂₅N₃O₅*ClH
• 分子量: 447.919
• InChiKey: WSLGMYBPTOIGSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2-hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)-1,2,3,6-tetrahydro-1-pyridyl]ethyl]benzoate hydrochloride 、 methyl 2-hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)piperidino]ethyl]benzoate hydrochloride 以above results in the formation of 2-hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)-1,2,3,6-tetrahydro-1-pyridyl]ethyl]benzamide hydrochloride的产率得到2-Hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)-1,2,3,6-tetrahydro-1-pyridyl]ethyl]benzamide 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-(2-溴-乙酰基)-2-羟基-苯甲酸甲酯 、 4-（2-酮酸-1-苯并咪唑）哌啶 在 sodium borohydrid 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 作用下， 以 N-甲基乙酰胺 、 甲醇 、 methanolic hydrogen chloride 、 ice-water 、 水 为溶剂， 生成 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α和β肾上腺素受体的阻断作用很有用。此外，这些化合物还具有解痉和降压活性。

  公开号：

  US04200755A1

文献信息

• 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.
• US4200755A
  申请人：——

  公开号：US4200755A

  公开（公告）日：1980-04-29