1-(5-甲氧基-1-苯并呋喃-3-基)丙-2-胺 | 140853-59-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 1-(5-甲氧基-1-苯并呋喃-3-基)丙-2-胺
• 中文别名: 1H-嘌呤-2,6-二酮,7-[(2S)-2,3-二羟基丙基]-3,7-二氢-1,3-二甲基-
• 英文名称: (R,S)-1-(5-methoxybenzofuran-3-yl)-2-aminopropane
• 英文别名: 1-(5-Methoxy-1-benzofuran-3-yl)propan-2-amine
• CAS: 140853-59-4
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: PMAFEFSQHHKAKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(5-甲氧基-1-苯并呋喃-3-基)丙烷-2-酮 在 lithium aluminium tetrahydride 、 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.5h， 生成 1-(5-甲氧基-1-苯并呋喃-3-基)丙-2-胺
  参考文献：
  名称：

  Benzofuran bioisosteres of hallucinogenic tryptamines

  摘要：

  The benzofuran analogues of the hallucinogens 5-methoxy-NN-dimethyltryptamine and 5-methoxy-alpha-methyl-tryptamine were synthesized and evaluated for affinity at the serotonin 5-HT2 and 5-HT1A receptors in rat brain homogenate, labeled with [I-125]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane ([I-125]DOI) and [H-3]-8-hydroxy-2-(N,N-di-n-propylamino)tetralin ([H-3]-8-OH-DPAT), respectively. At the 5-HT2 receptor, the benzofurans had slightly decreased affinities, approximately one-third and one-sixth those of the indoles, for the primary amines and the tertiary amines, respectively. The benzofurans also had lower affinity at the 5-HTA1A receptor, but decreased only about 20-30% from that of the indole isosteres. Thus, the 5-HT1A receptor is less discriminating with respect to preference for an indole versus a benzofuran, although all of the compounds did have higher affinities for the 5-HT2 receptor than for the 5-HT1A receptor. It is suggested that benzofurans may be useful in the design of serotonin receptor ligands.

  DOI：

  10.1021/jm00089a017

文献信息

• Benzofuran bioisosteres of hallucinogenic tryptamines
  作者：Zbigniew Tomaszewski、Michael P. Johnson、Xuemei Huang、David E. Nichols

  DOI：10.1021/jm00089a017

  日期：1992.5

  The benzofuran analogues of the hallucinogens 5-methoxy-NN-dimethyltryptamine and 5-methoxy-alpha-methyl-tryptamine were synthesized and evaluated for affinity at the serotonin 5-HT2 and 5-HT1A receptors in rat brain homogenate, labeled with [I-125]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane ([I-125]DOI) and [H-3]-8-hydroxy-2-(N,N-di-n-propylamino)tetralin ([H-3]-8-OH-DPAT), respectively. At the 5-HT2 receptor, the benzofurans had slightly decreased affinities, approximately one-third and one-sixth those of the indoles, for the primary amines and the tertiary amines, respectively. The benzofurans also had lower affinity at the 5-HTA1A receptor, but decreased only about 20-30% from that of the indole isosteres. Thus, the 5-HT1A receptor is less discriminating with respect to preference for an indole versus a benzofuran, although all of the compounds did have higher affinities for the 5-HT2 receptor than for the 5-HT1A receptor. It is suggested that benzofurans may be useful in the design of serotonin receptor ligands.