2-amino-1-(2-((2-methoxynaphthalen-6-yl)methyl)phenyl)ethanol | 1218996-96-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-1-(2-((2-methoxynaphthalen-6-yl)methyl)phenyl)ethanol
• CAS: 1218996-96-3
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: ZFUICJPLPHIEIO-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  2-amino-1-(2-((2-methoxynaphthalen-6-yl)methyl)phenyl)ethanol 在 甲烷磺酸 作用下， 反应 1.0h， 以26%的产率得到(7,12-dihydro-3-methoxytetraphen-12-yl)methanamine
  参考文献：
  名称：

  9-Aminomethyl-9,10-dihydroanthracene (AMDA) analogs as structural probes for steric tolerance in 5-HT2A and H1 receptor binding sites

  摘要：

  Synthesis, radioligand binding and molecular modeling studies of several 9-aminomethyl-9,10-dihydroanthracene (AMDA) analogs were carried out to determine the extent of the steric tolerance associated with expansion of the tricyclic ring system and amine substitution at 5-HT2A and H-1 receptors. A mixture of (7,12-dihydrotetraphene-12-yl)methanamine and (6,11-dihydrotetracene-11-yl)methanamine in a 75-25% ratio was found to have an apparent K-i of 10 nM at the 5-HT2A receptor. A substantial binding affinity for (7,12-dihydrotetraphene-3-methoxy-12-yl)methanamine at the 5-HT2A receptor (K-i = 21 nM) was also observed. Interestingly, this compound was found to have 100-fold selectivity for 5-HT2A over the H-1 receptor (K-i = 2500 nM). N-Phenylalkyl-AMDA derivatives, in which the length of the alkyl chain varied from methylene to n-butylene, were found to have only weak affinity for both 5-HT2A and H-1 receptors (K-i = 223 to 964 nM). Our results show that large rigid annulated AMDA analogs can be sterically accommodated within the proposed 5-HT2A binding site. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.064
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 二氯甲烷 为溶剂， 以0.75 g的产率得到2-amino-1-(2-((2-methoxynaphthalen-6-yl)methyl)phenyl)ethanol
  参考文献：
  名称：

  9-Aminomethyl-9,10-dihydroanthracene (AMDA) analogs as structural probes for steric tolerance in 5-HT2A and H1 receptor binding sites

  摘要：

  Synthesis, radioligand binding and molecular modeling studies of several 9-aminomethyl-9,10-dihydroanthracene (AMDA) analogs were carried out to determine the extent of the steric tolerance associated with expansion of the tricyclic ring system and amine substitution at 5-HT2A and H-1 receptors. A mixture of (7,12-dihydrotetraphene-12-yl)methanamine and (6,11-dihydrotetracene-11-yl)methanamine in a 75-25% ratio was found to have an apparent K-i of 10 nM at the 5-HT2A receptor. A substantial binding affinity for (7,12-dihydrotetraphene-3-methoxy-12-yl)methanamine at the 5-HT2A receptor (K-i = 21 nM) was also observed. Interestingly, this compound was found to have 100-fold selectivity for 5-HT2A over the H-1 receptor (K-i = 2500 nM). N-Phenylalkyl-AMDA derivatives, in which the length of the alkyl chain varied from methylene to n-butylene, were found to have only weak affinity for both 5-HT2A and H-1 receptors (K-i = 223 to 964 nM). Our results show that large rigid annulated AMDA analogs can be sterically accommodated within the proposed 5-HT2A binding site. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.064