S 24773 | 225786-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: S 24773
• 英文别名: N-{2-[7-methoxy-3-(3-aminophenyl)-1-naphthyl]ethyl}acetamide；N-[2-[3-(3-aminophenyl)-7-methoxynaphthalen-1-yl]ethyl]acetamide
• CAS: 225786-69-6
• 化学式: C₂₁H₂₂N₂O₂
• 分子量: 334.418
• InChiKey: RUYDBTKHRKQOLY-UHFFFAOYSA-N

物化性质

• 沸点：
  618.3±55.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 S 24773 在 sodium cyanoborohydride 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以37%的产率得到N-[2-(3-(3-Dimethylaminophenyl)-7-methoxynaphth-1-yl)ethyl]acetamide
  参考文献：
  名称：

  Synthesis of 3-phenylnaphthalenic derivatives as new selective MT2 melatoninergic ligands

  摘要：

  A series of naphthalenic analogues of melatonin were prepared and evaluated as melatonin receptor MT(2) selective ligands. Activity and MT(2) selectivity can be modulated with suitable variations of the C-3 phenyl and the acyl group on the C-1 side chain. Surprisingly, in contrast with what had been previously described in other series (2-benzylindoles, 2-benzylbenzofurans and 3-phenyltetralins), the presence of a C-3 phenyl with a functional group on the meta position seems to be primordial for MT2 afinity and selectivity. Indeed,N-[2-( 3-(3-hydroxymethylphenyl)-7-methoxynaphth-1-yl) ethyl] acetamide (21) is one of the best MT(2) selective ligands described until now and behaves as an antagonist. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.052
• 作为产物：
  描述：

  N-[2-(3-(3-nitrophenyl)-7-methoxynaphth-1-yl)ethyl]acetamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 S 24773
  参考文献：
  名称：

  Synthesis of 3-phenylnaphthalenic derivatives as new selective MT2 melatoninergic ligands

  摘要：

  A series of naphthalenic analogues of melatonin were prepared and evaluated as melatonin receptor MT(2) selective ligands. Activity and MT(2) selectivity can be modulated with suitable variations of the C-3 phenyl and the acyl group on the C-1 side chain. Surprisingly, in contrast with what had been previously described in other series (2-benzylindoles, 2-benzylbenzofurans and 3-phenyltetralins), the presence of a C-3 phenyl with a functional group on the meta position seems to be primordial for MT2 afinity and selectivity. Indeed,N-[2-( 3-(3-hydroxymethylphenyl)-7-methoxynaphth-1-yl) ethyl] acetamide (21) is one of the best MT(2) selective ligands described until now and behaves as an antagonist. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.052

文献信息

• Nouveaux composés naphtaléniques, leur procédé de préparation et les compositions pharmaceutiques quiles contiennent
  申请人：ADIR ET COMPAGNIE

  公开号：EP0919541A1

  公开（公告）日：1999-06-02

  Composé de formule (I) : dans laquelle : T représente une chaîne alkylène, A et B forment ensemble un groupement naphtalène, dihydronaphtalène, ou tétrahydronapthalène, R représente un hydrogène, un groupement hydroxy, R' ou OR', R' étant tel que défini dans la description, G1 représente un halogène, un radical R1 ou un groupement -O-CO-R1, R1 étant tel que défini dans la description, G2 représente un groupement choisi parmi : X, R2 et R21 étant tels que définis dans la description. Medicaments

  式 (I) 的化合物 其中： T 代表亚烷基链、 A 和 B 共同形成萘、二氢萘或四氢萘基团、 R 代表氢、羟基、R'或 OR'基团，R'如说明中所定义、 G1 代表卤素、基团 R1 或基团-O-CO-R1，其中 R1 如说明中所定义、 G2 代表选自......的基团 X、R2 和 R21 如说明中所定义。 药物
• Nouveaux composés naphtaléniques, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：LES LABORATOIRES SERVIER

  公开号：EP0919541B1

  公开（公告）日：2005-08-10
• US6143789A
  申请人：——

  公开号：US6143789A

  公开（公告）日：2000-11-07
• Synthesis of 3-phenylnaphthalenic derivatives as new selective MT2 melatoninergic ligands
  作者：Sophie Poissonnier-Durieux、Mohamed Ettaoussi、Basile Pérès、Jean A. Boutin、Valérie Audinot、Caroline Bennejean、Philippe Delagrange、Daniel Henri Caignard、Pierre Renard、Pascal Berthelot、Daniel Lesieur、Saïd Yous

  DOI：10.1016/j.bmc.2008.08.052

  日期：2008.9

  A series of naphthalenic analogues of melatonin were prepared and evaluated as melatonin receptor MT(2) selective ligands. Activity and MT(2) selectivity can be modulated with suitable variations of the C-3 phenyl and the acyl group on the C-1 side chain. Surprisingly, in contrast with what had been previously described in other series (2-benzylindoles, 2-benzylbenzofurans and 3-phenyltetralins), the presence of a C-3 phenyl with a functional group on the meta position seems to be primordial for MT2 afinity and selectivity. Indeed,N-[2-( 3-(3-hydroxymethylphenyl)-7-methoxynaphth-1-yl) ethyl] acetamide (21) is one of the best MT(2) selective ligands described until now and behaves as an antagonist. (C) 2008 Elsevier Ltd. All rights reserved.