(+)-(S)-2-[(3-methoxyphenyl)thio]propan-1-ol | 1252084-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+)-(S)-2-[(3-methoxyphenyl)thio]propan-1-ol
• CAS: 1252084-96-0
• 化学式: C₁₀H₁₄O₂S
• 分子量: 198.286
• InChiKey: FGUHDUTZFNAKSA-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  邻苯二甲酸亚胺 、 (+)-(S)-2-[(3-methoxyphenyl)thio]propan-1-ol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到(-)-(S)-2-(2-[(3-methoxyphenyl)thio]propyl)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.06.100
• 作为产物：
  描述：

  (-)-(S)-methyl 2-[(3-methoxyphenyl)thio]propanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(+)-(S)-2-[(3-methoxyphenyl)thio]propan-1-ol
  参考文献：
  名称：

  Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.06.100

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.