methyl 5-(2-{[3-(1,3-benzodioxol-5-yl)-1-methylpropyl]amino}-1-hydroxyethyl)-2-hydroxybenzoate hydrochloride | 56290-92-7

• 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 5-(2-{[3-(1,3-benzodioxol-5-yl)-1-methylpropyl]amino}-1-hydroxyethyl)-2-hydroxybenzoate hydrochloride
• 英文别名: Methyl 5-[2-[4-(1,3-benzodioxol-5-yl)butan-2-ylamino]-1-hydroxyethyl]-2-hydroxybenzoate;hydrochloride
• CAS: 56290-92-7
• 化学式: C₂₁H₂₅NO₆*ClH
• 分子量: 423.894
• InChiKey: XGNJWXYQQXGKRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.2
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 5-(2-{[3-(1,3-benzodioxol-5-yl)-1-methylpropyl]amino}-1-hydroxyethyl)-2-hydroxybenzoate hydrochloride 在 ammonium hydroxide 作用下， 反应 192.0h， 以81%的产率得到5-[2-[[3-(1,3-苯并二氧戊环-5-基)-1-甲基丙基]氨基]-1-羟基乙基]水杨酰胺单盐酸盐
  参考文献：
  名称：

  来自水杨酰胺的芳基乙醇胺具有α-和β-肾上腺素受体阻断活性。拉贝洛尔，其对映异构体和相关水杨酰胺的制备。

  摘要：

  已经制备了一系列基于水杨酰胺的苯乙醇胺（3），并显示出具有β-肾上腺素阻断特性。当碱性氮原子被某些芳烷基取代时，这些化合物也会封闭α-肾上腺素受体。1-甲基-3-苯基丙基衍生物拉贝洛尔（34）在动物和人类中均具有降压作用，并描述了其四种立体异构体的合成。在两个不对称中心具有R构型的对映体90具有大部分的β-阻断活性，但是几乎没有α-阻断活性。在醇碳上具有S构型并且在氨基取代基上具有R构型的化合物主要是α-肾上腺素受体阻断剂89。

  DOI：

  10.1021/jm00348a013
• 作为产物：
  描述：

  5-[2-(3-Benzo[1,3]dioxol-5-yl-1-methyl-propylamino)-acetyl]-2-hydroxy-benzoic acid methyl ester; hydrochloride 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 11.5h， 以74%的产率得到methyl 5-(2-{[3-(1,3-benzodioxol-5-yl)-1-methylpropyl]amino}-1-hydroxyethyl)-2-hydroxybenzoate hydrochloride
  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

• CLIFTON, J. E.;COLLINS, I.;HALLETT, P.;HARTLEY, D.;LUNTS, L. H. C.;WICKS,+, J. MED. CHEM., 1982, 25, N 6, 670-679
  作者：CLIFTON, J. E.、COLLINS, I.、HALLETT, P.、HARTLEY, D.、LUNTS, L. H. C.、WICKS,+

  DOI：——

  日期：——