(+/-)-N-<1-<(4-hydroxyphenyl)thio>-2-propyl>acetamide | 128008-74-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (+/-)-N-<1-<(4-hydroxyphenyl)thio>-2-propyl>acetamide
• 英文别名: N-[1-(4-hydroxyphenyl)sulfanylpropan-2-yl]acetamide
• CAS: 128008-74-2
• 化学式: C₁₁H₁₅NO₂S
• 分子量: 225.312
• InChiKey: WTTFAZFFUMIJNC-UHFFFAOYSA-N

物化性质

• 沸点：
  457.1±30.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-N-<1-<(4-hydroxyphenyl)thio>-2-propyl>acetamide 在 盐酸 作用下， 反应 12.0h， 以95%的产率得到1-<(4-hydroxyphenyl)thio>-2-propylamine hydrochloride
  参考文献：
  名称：

  Antihypertensive activities of phenyl aminoethyl sulfides, a class of synthetic substrates for dopamine .beta.-hydroxylase

  摘要：

  Four sulfur-containing analogues of phenylpropylamine were synthesized and evaluated as substrates for dopamine beta-hydroxylase (DBH) and monoamine oxidase (MAO). All four phenyl aminoethyl sulfides were shown to be good substrates for DBH whereas only the two analogues not possessing a methyl group alpha to the terminal amino group were substrates for MAO. All four analogues were tested for acute antihypertensive activity in an animal model for hypertension, the spontaneously hypertensive rat (SHR). Two of the analogues, both of which should partition readily across the blood-brain barrier, did not appreciably reduce systemic blood pressure in the 6-h testing period. However, the two analogues that were designed to be relatively restricted to peripheral sites of action caused a dramatic drop in blood pressure in SHR of 25% within 1-1.5-h postinjection, with the analogue designed to be both restricted to the periphery and MAO inactive, causing a more prolonged antihypertensive activity.

  DOI：

  10.1021/jm00376a024
• 作为产物：
  描述：

  (+/-)-2,4-dimethyl-2-oxazoline 、 4-羟基苯硫酚 反应 2.0h， 生成 (+/-)-N-<1-<(4-hydroxyphenyl)thio>-2-propyl>acetamide
  参考文献：
  名称：

  Antihypertensive activities of phenyl aminoethyl sulfides, a class of synthetic substrates for dopamine .beta.-hydroxylase

  摘要：

  Four sulfur-containing analogues of phenylpropylamine were synthesized and evaluated as substrates for dopamine beta-hydroxylase (DBH) and monoamine oxidase (MAO). All four phenyl aminoethyl sulfides were shown to be good substrates for DBH whereas only the two analogues not possessing a methyl group alpha to the terminal amino group were substrates for MAO. All four analogues were tested for acute antihypertensive activity in an animal model for hypertension, the spontaneously hypertensive rat (SHR). Two of the analogues, both of which should partition readily across the blood-brain barrier, did not appreciably reduce systemic blood pressure in the 6-h testing period. However, the two analogues that were designed to be relatively restricted to peripheral sites of action caused a dramatic drop in blood pressure in SHR of 25% within 1-1.5-h postinjection, with the analogue designed to be both restricted to the periphery and MAO inactive, causing a more prolonged antihypertensive activity.

  DOI：

  10.1021/jm00376a024