N-((9,10-dihydroanthracen-9-yl)methyl)-3-phenylpropan-1-amine | 1218997-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-((9,10-dihydroanthracen-9-yl)methyl)-3-phenylpropan-1-amine
• 英文别名: N-(9,10-dihydroanthracen-9-ylmethyl)-3-phenylpropan-1-amine
• CAS: 1218997-06-8
• 化学式: C₂₄H₂₅N
• 分子量: 327.469
• InChiKey: UTYFBWKQSXSRBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-((9,10-dihydroanthracen-9-yl)methyl)-3-phenylpropan-1-amine 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以0.15 g的产率得到N-((9,10-dihydroanthracen-9-yl)methyl)-3-phenylpropan-1-amine hydrochloride
  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：

  9,10-dihydro-N-(3-phenylpropyl)anthracene-10-carboxamide 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 生成 N-((9,10-dihydroanthracen-9-yl)methyl)-3-phenylpropan-1-amine
  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