(+)-(R)-N-[1-methyl-2-(phenylthio)ethyl]acetamide | 1252084-86-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (+)-(R)-N-[1-methyl-2-(phenylthio)ethyl]acetamide
• 英文别名: N-[(2R)-1-phenylsulfanylpropan-2-yl]acetamide
• CAS: 1252084-86-8
• 化学式: C₁₁H₁₅NOS
• 分子量: 209.312
• InChiKey: DCKGVDQXKBHNLI-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(R)-N-[1-methyl-2-(phenylthio)ethyl]acetamide 在 盐酸 作用下， 反应 6.0h， 生成 (R)-1-(phenylthio)-2-aminopropane hydrochloride
  参考文献：
  名称：

  The enantiomeric specificity of the antihypertensive activity of 1-(phenylthio)-2-aminopropane, a synthetic substrate analog for dopamine .beta.-monooxygenase

  摘要：

  We have found that (R,S)-1-(phenylthio)-2-aminopropane (4a), a synthetic alternate substrate for the terminal enzyme of norepinephrine biosynthesis, dopamine beta-monooxygenase (DBM), is both an indirect sympathomimetic and a potent antihypertensive agent in spontaneously hypertensive rats. We demonstrate herein that there is a distinct enantiospecific difference in the activities of (R)-1-(phenylthio)-2-aminopropane (4b) and (S)-1-(phenylthio)-2-aminopropane (4c). We find that 4c, the more potent DBM substrate analogue, exhibits both the indirect sympathomimetic activity and the antihypertensive activity previously observed for the racemate and inhibits the active transport of catecholamines at the nerve terminal. In contrast, 4b, which is less potent as a DBM substrate or as an inhibitor of catecholamine uptake, does not exhibit an indirect sympathomimetic effect and is not an effective antihypertensive agent. These results suggest that the greater selectivity of the S enantiomer for both the catecholamine reuptake transporter and the target enzyme DBM accounts for its greater potency as an indirect-acting sympathomimetic agent as well as its activity as an antihypertensive agent. These results are also consistent with the hypothesized mechanism of action of this class of sulfur-containing DBM substrate analogues.

  DOI：

  10.1021/jm00107a031
• 作为产物：
  描述：

  (R)-2,4-dimethyl-2-oxazoline 、 苯硫酚 反应 6.0h， 生成 (+)-(R)-N-[1-methyl-2-(phenylthio)ethyl]acetamide
  参考文献：
  名称：

  The enantiomeric specificity of the antihypertensive activity of 1-(phenylthio)-2-aminopropane, a synthetic substrate analog for dopamine .beta.-monooxygenase

  摘要：

  We have found that (R,S)-1-(phenylthio)-2-aminopropane (4a), a synthetic alternate substrate for the terminal enzyme of norepinephrine biosynthesis, dopamine beta-monooxygenase (DBM), is both an indirect sympathomimetic and a potent antihypertensive agent in spontaneously hypertensive rats. We demonstrate herein that there is a distinct enantiospecific difference in the activities of (R)-1-(phenylthio)-2-aminopropane (4b) and (S)-1-(phenylthio)-2-aminopropane (4c). We find that 4c, the more potent DBM substrate analogue, exhibits both the indirect sympathomimetic activity and the antihypertensive activity previously observed for the racemate and inhibits the active transport of catecholamines at the nerve terminal. In contrast, 4b, which is less potent as a DBM substrate or as an inhibitor of catecholamine uptake, does not exhibit an indirect sympathomimetic effect and is not an effective antihypertensive agent. These results suggest that the greater selectivity of the S enantiomer for both the catecholamine reuptake transporter and the target enzyme DBM accounts for its greater potency as an indirect-acting sympathomimetic agent as well as its activity as an antihypertensive agent. These results are also consistent with the hypothesized mechanism of action of this class of sulfur-containing DBM substrate analogues.

  DOI：

  10.1021/jm00107a031

文献信息

• Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors
  作者：Alessia Carocci、Alessia Catalano、Angelo Lovece、Giovanni Lentini、Andrea Duranti、Valeria Lucini、Marilou Pannacci、Francesco Scaglione、Carlo Franchini

  DOI：10.1016/j.bmc.2010.06.100

  日期：2010.9

  A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT1 and MT2 receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists. (C) 2010 Elsevier Ltd. All rights reserved.
• The enantiomeric specificity of the antihypertensive activity of 1-(phenylthio)-2-aminopropane, a synthetic substrate analog for dopamine .beta.-monooxygenase
  作者：Heath H. Herman、Philip A. Husain、James E. Colbert、Margaret M. Schweri、Stanley H. Pollock、Lydia C. Fowler、Sheldon W. May

  DOI：10.1021/jm00107a031

  日期：1991.3

  We have found that (R,S)-1-(phenylthio)-2-aminopropane (4a), a synthetic alternate substrate for the terminal enzyme of norepinephrine biosynthesis, dopamine beta-monooxygenase (DBM), is both an indirect sympathomimetic and a potent antihypertensive agent in spontaneously hypertensive rats. We demonstrate herein that there is a distinct enantiospecific difference in the activities of (R)-1-(phenylthio)-2-aminopropane (4b) and (S)-1-(phenylthio)-2-aminopropane (4c). We find that 4c, the more potent DBM substrate analogue, exhibits both the indirect sympathomimetic activity and the antihypertensive activity previously observed for the racemate and inhibits the active transport of catecholamines at the nerve terminal. In contrast, 4b, which is less potent as a DBM substrate or as an inhibitor of catecholamine uptake, does not exhibit an indirect sympathomimetic effect and is not an effective antihypertensive agent. These results suggest that the greater selectivity of the S enantiomer for both the catecholamine reuptake transporter and the target enzyme DBM accounts for its greater potency as an indirect-acting sympathomimetic agent as well as its activity as an antihypertensive agent. These results are also consistent with the hypothesized mechanism of action of this class of sulfur-containing DBM substrate analogues.