2-methoxy-9-aminomethyl-9,10-dihydroanthracene | 1082389-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-methoxy-9-aminomethyl-9,10-dihydroanthracene
• 英文别名: 2-methoxy-AMDA；(2-methoxy-9,10-dihydroanthracen-9-yl)methanamine
• CAS: 1082389-19-2
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: UKAGNBPAZOMJAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2-(2-amino-1-(3-methoxyphenyl)ethyl)phenyl)methanol 在 PPE 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以30%的产率得到2-methoxy-9-aminomethyl-9,10-dihydroanthracene
  参考文献：
  名称：

  Methoxy-substituted 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives exhibit differential binding affinities at the 5-HT2A receptor

  摘要：

  The effects of methoxy-substitution at the 1-, 2-, 3-, and 4-positions of 9-aminomethyl-9,10-dihydroanthracene (AMDA) on h5-HT2A receptor affinity were determined. Racemic mixtures of these compounds were found to show the following affinity trend: 3-MeO > 4-MeO > 1-MeO similar to 2-MeO. Comparison of the effects of these substitutions, with the aid of computational molecular modeling techniques, suggest that the various positional and stereochemical isomers of the methoxy-substituted AMDA compounds interact differently with the h5-HT2A receptor. It is predicted that for the compounds with higher affinities, the methoxy oxygen atom is able to interact with hydrogen bond-donating sidechains within alternative h5-HT2A receptor binding sites, whereas the lower-affinity isomers lack this ability. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.059

文献信息

• Methoxy-substituted 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives exhibit differential binding affinities at the 5-HT2A receptor
  作者：Gajanan K. Dewkar、Srinivas Peddi、Philip D. Mosier、Bryan L. Roth、Richard B. Westkaemper

  DOI：10.1016/j.bmcl.2008.08.059

  日期：2008.10

  The effects of methoxy-substitution at the 1-, 2-, 3-, and 4-positions of 9-aminomethyl-9,10-dihydroanthracene (AMDA) on h5-HT2A receptor affinity were determined. Racemic mixtures of these compounds were found to show the following affinity trend: 3-MeO > 4-MeO > 1-MeO similar to 2-MeO. Comparison of the effects of these substitutions, with the aid of computational molecular modeling techniques, suggest that the various positional and stereochemical isomers of the methoxy-substituted AMDA compounds interact differently with the h5-HT2A receptor. It is predicted that for the compounds with higher affinities, the methoxy oxygen atom is able to interact with hydrogen bond-donating sidechains within alternative h5-HT2A receptor binding sites, whereas the lower-affinity isomers lack this ability. (c) 2008 Elsevier Ltd. All rights reserved.