N-[2-(7-{4-[8-(2-tert-butoxycarbonylaminoethyl)naphthalen-2-yloxy]butoxy}naphthalen-1-yl)ethyl]carbamic acid tert-butyl ester | 296280-93-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[2-(7-{4-[8-(2-tert-butoxycarbonylaminoethyl)naphthalen-2-yloxy]butoxy}naphthalen-1-yl)ethyl]carbamic acid tert-butyl ester
• CAS: 296280-93-8
• 化学式: C₃₈H₄₈N₂O₆
• 分子量: 628.809
• InChiKey: QLSXBINGNUYKLU-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  N-[2-(7-{4-[8-(2-tert-butoxycarbonylaminoethyl)naphthalen-2-yloxy]butoxy}naphthalen-1-yl)ethyl]carbamic acid tert-butyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以75%的产率得到2-[7-(4-{8-(2-aminoethyl)naphthalen-2-yloxy}butoxy)naphthalen-1-yl]ethylamine dihydrochloride
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of novel naphthalenic derivatives as selective MT1 melatoninergic ligands

  摘要：

  Novel heterodimer analogues of melatonin were synthesized, when agomelatine (1) and various aryl units are linked via a linear alkyl chain through the methoxy group. The compounds were tested for their actions at melatonin receptors. Several of these ligands are MT1-selective with nanomolar or subnanomolar affinity. In addition, while most of the derivatives behave as partial agonists on one or both receptor subtypes, N-[2-(7-{4-[6-(1-methoxycarbonylethyl)naphthalen-2-yloxy]butoxy}naphthalen-1-yl)ethyl]acetamide (36), a subnanomolar MT1 ligand with an 11-fold preference over MT2 receptors, is a full antagonist on both receptors. Our results also confirm that the selectivity seen for the MT1 receptor arises predominantly from steric factors and is not a consequence of the bridging of melatonin receptor dimers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.008
• 作为产物：
  描述：

  1,4-二溴丁烷 、 [2-(7-hydroxynaphthalen-1-yl)ethyl]carbamic acid tert-butyl ester 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以68%的产率得到N-[2-(7-{4-[8-(2-tert-butoxycarbonylaminoethyl)naphthalen-2-yloxy]butoxy}naphthalen-1-yl)ethyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of novel naphthalenic derivatives as selective MT1 melatoninergic ligands

  摘要：

  Novel heterodimer analogues of melatonin were synthesized, when agomelatine (1) and various aryl units are linked via a linear alkyl chain through the methoxy group. The compounds were tested for their actions at melatonin receptors. Several of these ligands are MT1-selective with nanomolar or subnanomolar affinity. In addition, while most of the derivatives behave as partial agonists on one or both receptor subtypes, N-[2-(7-{4-[6-(1-methoxycarbonylethyl)naphthalen-2-yloxy]butoxy}naphthalen-1-yl)ethyl]acetamide (36), a subnanomolar MT1 ligand with an 11-fold preference over MT2 receptors, is a full antagonist on both receptors. Our results also confirm that the selectivity seen for the MT1 receptor arises predominantly from steric factors and is not a consequence of the bridging of melatonin receptor dimers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.008