3-甲氧基-9-氨基甲基-9,10-二氢蒽 | 1075741-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 3-甲氧基-9-氨基甲基-9,10-二氢蒽
• 英文名称: 3-methoxy-9-aminomethyl-9,10-dihydroanthracene
• 英文别名: 3-methoxy-AMDA；(3-methoxy-9,10-dihydroanthracen-9-yl)methanamine
• CAS: 1075741-20-6
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: DTEPCKRLYVEVEM-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

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  3-甲氧基-9-氨基甲基-9,10-二氢蒽 在 氢溴酸 作用下， 以 乙醚 为溶剂， 生成 3-methoxy-9-aminomethyl-9,10-dihydroanthracene hydrobromide
  参考文献：
  名称：

  Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT_2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation

  摘要：

  The effects of 3-position substitution of 9-aminomethyl-9,10-dihydroanthracene (AMDA) on 5-HT2A receptor affinity were determined and compared to a parallel series of DOB-like 1-(2,5-dimethoxyphenyl)-2-aminopropanes substituted at the 4-position. The results were interpreted within the context of 5-HT2A receptor models that suggest that members of the DOB-like series call bind to the receptor in two distinct modes that correlate with the compounds' functional activity. Automated ligand docking and molecular dynamics suggest that all of the AMDA derivatives, the parent of which is a 5-HT2A antagonist, bind in a fashion analogous to that for the sterically demanding antagonist DOB-like compounds. The failure of the F340(6.52)L mutation to adversely affect the affinity of AMDA and the 3-bromo derivative is consistent with the proposed modes of orientation. Evaluation of ligand-receptor complex models suggest that a valine/threonine exchange between the 5-HT2A and D-2 receptors may be the origin of selectivity for AMDA and two substituted derivatives.

  DOI：

  10.1021/jm800771x
• 作为产物：
  描述：

  2-amino-1-[2-(3-methoxybenzyl)phenyl]ethanol 在 甲烷磺酸 作用下， 反应 12.0h， 以35%的产率得到3-甲氧基-9-氨基甲基-9,10-二氢蒽
  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.
• Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT_2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation
  作者：Scott P. Runyon、Philip D. Mosier、Bryan L. Roth、Richard A. Glennon、Richard B. Westkaemper

  DOI：10.1021/jm800771x

  日期：2008.11.13

  The effects of 3-position substitution of 9-aminomethyl-9,10-dihydroanthracene (AMDA) on 5-HT2A receptor affinity were determined and compared to a parallel series of DOB-like 1-(2,5-dimethoxyphenyl)-2-aminopropanes substituted at the 4-position. The results were interpreted within the context of 5-HT2A receptor models that suggest that members of the DOB-like series call bind to the receptor in two distinct modes that correlate with the compounds' functional activity. Automated ligand docking and molecular dynamics suggest that all of the AMDA derivatives, the parent of which is a 5-HT2A antagonist, bind in a fashion analogous to that for the sterically demanding antagonist DOB-like compounds. The failure of the F340(6.52)L mutation to adversely affect the affinity of AMDA and the 3-bromo derivative is consistent with the proposed modes of orientation. Evaluation of ligand-receptor complex models suggest that a valine/threonine exchange between the 5-HT2A and D-2 receptors may be the origin of selectivity for AMDA and two substituted derivatives.