[2-(7-hydroxynaphthalen-1-yl)ethyl]carbamic acid tert-butyl ester | 296280-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [2-(7-hydroxynaphthalen-1-yl)ethyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-(7-hydroxynaphthalen-1-yl)ethyl]carbamate
• CAS: 296280-81-4
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: VREDYJCWWJSOMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-(7-(4-bromobutoxy)naphthalen-1-yl)ethyl]-acetamide 、 [2-(7-hydroxynaphthalen-1-yl)ethyl]carbamic acid tert-butyl ester 在 potassium carbonate 作用下， 以 乙腈 、 acetonitrle 为溶剂， 反应 0.5h， 以81%的产率得到N-[2-(7-{4-[8-(2-acetylaminoethyl)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
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 2-(7-hydroxy-1-naphthyl)ethanamine hydrochloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以91%的产率得到[2-(7-hydroxynaphthalen-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

文献信息

• Substituted dimeric compounds
  申请人：——

  公开号：US20020035114A1

  公开（公告）日：2002-03-21

  The invention relates to compounds of formula (I): A—G 1 —Cy—G 2 —Cy—G 3 —B  (I) wherein: A represents NR 1 C(Q)R 2 , C(Q)NR 2 R 3 or NR 1 C(Q)NR 2 R 3 , B represents NR 1 C(Q)R 2 , C(Q)NR 2 R 3 , NR 1 C(Q)NR 2 R 3 , C(Q)OR 1 , NR 1 C(Q)OR 2 or NR 2 R 3 , G 1 and G 3 represent an optionally substituted alkylene chain, Cy represents a ring structure 1 G 2 represents a chain and medicinal products containing the same which are useful in treating or in preventing melatoninergic disorders.

  本发明涉及式(I)的化合物：A-G1-Cy-G2-Cy-G3-B  (I)，其中：A代表NR1C(Q)R2，C(Q)NR2R3或NR1C(Q)NR2R3，B代表NR1C(Q)R2，C(Q)NR2R3，NR1C(Q)NR2R3，C(Q)OR1，NR1C(Q)OR2或NR2R3，G1和G3代表可选取代的烷基链，Cy代表环结构，G2代表链，以及含有这些化合物的药物，其在治疗或预防褪黑激素失调方面有用。
• US6319930B1
  申请人：——

  公开号：US6319930B1

  公开（公告）日：2001-11-20
• US6635650B2
  申请人：——

  公开号：US6635650B2

  公开（公告）日：2003-10-21