N-[2-(7-{4-[3-(2-acetylaminoethyl)benzofuran-5-yloxy]butoxy}naphthalen-1-yl)ethyl]-acetamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[2-(7-{4-[3-(2-acetylaminoethyl)benzofuran-5-yloxy]butoxy}naphthalen-1-yl)ethyl]-acetamide
• 英文别名: N-(2-{7-[4-({3-[2-(acetylamino)ethyl]-1-benzofuran-5-yl}oxy)butoxy]-1-naphthyl}-ethyl)acetamide；N-[2-[7-[4-[[3-(2-acetamidoethyl)-1-benzofuran-5-yl]oxy]butoxy]naphthalen-1-yl]ethyl]acetamide
• 化学式: C₃₀H₃₄N₂O₅
• 分子量: 502.61
• InChiKey: BIXNYPIXYPNFDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-Hydroxy-3-(2-acetamino-ethyl)-benzofuran 、 N-[2-(7-(4-bromobutoxy)naphthalen-1-yl)ethyl]-acetamide 在 potassium carbonate 作用下， 以 乙腈 、 acetonitrle 为溶剂， 反应 0.5h， 以62%的产率得到N-[2-(7-{4-[3-(2-acetylaminoethyl)benzofuran-5-yloxy]butoxy}naphthalen-1-yl)ethyl]-acetamide
  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

文献信息

• Dérivés carboxamides dimériques substitués, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：ADIR ET COMPAGNIE

  公开号：EP1057826A1

  公开（公告）日：2000-12-06

  L'invention concerne les composés de formule (I) :         A-G1-Cy-G2-Cy'-G3-B     (I) dans laquelle : A représente un groupement NR1C(Q)R2, C(Q)NR2R3 ou NR1C(Q)NR2R3, B représente un groupement NR1C(Q)R2, NR1C(Q)NR2R3, C(Q)NR2R3, C(Q)OR1, NR1C(Q)OR2, NR2R1, G1, G3 représentent une chaîne alkylène éventuellement substituée, Cy et Cy', différents, représentent une structure cyclique ou G2 représente une chaîne Médicaments

  本发明涉及式 (I) 化合物： A-G1-Cy-G2-Cy'-G3-B (I) 其中： A 代表基团 NR1C(Q)R2、C(Q)NR2R3 或 NR1C(Q)NR2R3、 B 代表基团 NR1C(Q)R2、NR1C(Q)NR2R3、C(Q)NR2R3、C(Q)OR1、NR1C(Q)OR2、NR2R1、 G1、G3 代表任选取代的亚烷基链、 不同的 Cy 和 Cy'代表环状结构 或 G2 代表链 药品
• US6310074B1
  申请人：——

  公开号：US6310074B1

  公开（公告）日：2001-10-30
• Design, synthesis and pharmacological evaluation of novel naphthalenic derivatives as selective MT1 melatoninergic ligands
  作者：Christophe Mésangeau、Basile Pérès、Carole Descamps-François、Philippe Chavatte、Valérie Audinot、Sophie Coumailleau、Jean A. Boutin、Philippe Delagrange、Caroline Bennejean、Pierre Renard、Daniel H. Caignard、Pascal Berthelot、Saïd Yous

  DOI：10.1016/j.bmc.2010.04.008

  日期：2010.5

  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.