(2,7-dimethoxy-1-naphthyl)methyl chloride | 179041-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2,7-dimethoxy-1-naphthyl)methyl chloride
• 英文别名: 1-(Chloromethyl)-2,7-dimethoxynaphthalene
• CAS: 179041-52-2
• 化学式: C₁₃H₁₃ClO₂
• 分子量: 236.698
• InChiKey: IRTFYRHUSRYFES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2,7-dimethoxy-1-naphthyl)methyl chloride 在 sodium hydroxide 、 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 26.67h， 生成 4-(2,7-Dimethoxy-naphthalen-1-ylmethyl)-2-methyl-4H-oxazol-5-one
  参考文献：
  名称：

  Synthesis of 2-Amido-2,3-dihydro-1H-phenalene Derivatives as New Conformationally Restricted Ligands for Melatonin Receptors

  摘要：

  Tetrahydroanthracene, tetrahydrophenanthrene, and tetrahydrophenalene moieties were used to design novel constrained melatoninergic agents. Compounds 1 and 2 were synthesized from the cyclization of the aryl succinic acids 6a,b followed by catalytic reduction, Curtius degradation to the amino derivatives, and acetylation. The phenalene derivatives 3 were prepared by cyclization of the aza lactones of the corresponding alpha-N-acetyl amino acids. The ketone derivatives were reduced directly by catalytic hydrogenation to produce the compounds 3. The different compounds were evaluated in vitro in binding assays using 2-[I-125]iodomelatonin and chicken brain membranes. Melatonin and 2-acetamido-8-methoxytetralin were used as the reference compounds. The results showed the superiority of the dihydrophenalene framework 3 over tho se of tetrahydro anthracene and tetrahydrophenanthrene. 3a had relatively good affinity for melatonin receptors (K-i = 28.7 nM). Introduction of an additional methoxy group gave a derivative (3c) with nanomolar affinity (K-i = 0.7 nM), confirming the existence of a secondary binding site in the receptor which has been described previously. An increase in the affinity was also observed with the propionamido derivative 3e (K-i = 6.0 nM). The potential agonist properties of the compound 3e were evaluated on the dermal melanocytes of Xenopus laevis tadpoles. At the concentration of 2.3 nM (5 x K-i), melatonin gave melanophore index value of 1. Similarly to melatonin, 3e was shown to be a potent agonist of the melanosome aggregation.

  DOI：

  10.1021/jm960219h
• 作为产物：
  描述：

  (2,7-dimethoxynaphth-1-yl)methanol 在 吡啶 、 氯化亚砜 作用下， 以 甲苯 为溶剂， 以94%的产率得到(2,7-dimethoxy-1-naphthyl)methyl chloride
  参考文献：
  名称：

  Synthesis of 2-Amido-2,3-dihydro-1H-phenalene Derivatives as New Conformationally Restricted Ligands for Melatonin Receptors

  摘要：

  Tetrahydroanthracene, tetrahydrophenanthrene, and tetrahydrophenalene moieties were used to design novel constrained melatoninergic agents. Compounds 1 and 2 were synthesized from the cyclization of the aryl succinic acids 6a,b followed by catalytic reduction, Curtius degradation to the amino derivatives, and acetylation. The phenalene derivatives 3 were prepared by cyclization of the aza lactones of the corresponding alpha-N-acetyl amino acids. The ketone derivatives were reduced directly by catalytic hydrogenation to produce the compounds 3. The different compounds were evaluated in vitro in binding assays using 2-[I-125]iodomelatonin and chicken brain membranes. Melatonin and 2-acetamido-8-methoxytetralin were used as the reference compounds. The results showed the superiority of the dihydrophenalene framework 3 over tho se of tetrahydro anthracene and tetrahydrophenanthrene. 3a had relatively good affinity for melatonin receptors (K-i = 28.7 nM). Introduction of an additional methoxy group gave a derivative (3c) with nanomolar affinity (K-i = 0.7 nM), confirming the existence of a secondary binding site in the receptor which has been described previously. An increase in the affinity was also observed with the propionamido derivative 3e (K-i = 6.0 nM). The potential agonist properties of the compound 3e were evaluated on the dermal melanocytes of Xenopus laevis tadpoles. At the concentration of 2.3 nM (5 x K-i), melatonin gave melanophore index value of 1. Similarly to melatonin, 3e was shown to be a potent agonist of the melanosome aggregation.

  DOI：

  10.1021/jm960219h

文献信息

• Tricyclic amides
  申请人：Adir et Compagnie

  公开号：US05712312A1

  公开（公告）日：1998-01-27

  The invention relates to a compound selected from these of formula (I): ##STR1## in which R.sub.7, R.sub.8, Y, n and A are as defined in the description, and medicinal product containing the same useful for treating a disorder of the melatoninergic system.

  该发明涉及一种选择自以下公式(I)的化合物：##STR1## 其中R.sub.7，R.sub.8，Y，n和A如描述中定义，并含有相同化合物的药物产品，适用于治疗褪黑激素系统障碍。
• US5712312A
  申请人：——

  公开号：US5712312A

  公开（公告）日：1998-01-27
• US5849781A
  申请人：——

  公开号：US5849781A

  公开（公告）日：1998-12-15
• Synthesis of 2-Amido-2,3-dihydro-1<i>H</i>-phenalene Derivatives as New Conformationally Restricted Ligands for Melatonin Receptors
  作者：Monique Mathé-Allainmat、Florence Gaudy、Sames Sicsic、Anne-Laure Dangy-Caye、Shuren Shen、Béatrice Brémont、Zohra Benatalah、Michel Langlois、Pierre Renard、Philippe Delagrange

  DOI：10.1021/jm960219h

  日期：1996.1.1

  Tetrahydroanthracene, tetrahydrophenanthrene, and tetrahydrophenalene moieties were used to design novel constrained melatoninergic agents. Compounds 1 and 2 were synthesized from the cyclization of the aryl succinic acids 6a,b followed by catalytic reduction, Curtius degradation to the amino derivatives, and acetylation. The phenalene derivatives 3 were prepared by cyclization of the aza lactones of the corresponding alpha-N-acetyl amino acids. The ketone derivatives were reduced directly by catalytic hydrogenation to produce the compounds 3. The different compounds were evaluated in vitro in binding assays using 2-[I-125]iodomelatonin and chicken brain membranes. Melatonin and 2-acetamido-8-methoxytetralin were used as the reference compounds. The results showed the superiority of the dihydrophenalene framework 3 over tho se of tetrahydro anthracene and tetrahydrophenanthrene. 3a had relatively good affinity for melatonin receptors (K-i = 28.7 nM). Introduction of an additional methoxy group gave a derivative (3c) with nanomolar affinity (K-i = 0.7 nM), confirming the existence of a secondary binding site in the receptor which has been described previously. An increase in the affinity was also observed with the propionamido derivative 3e (K-i = 6.0 nM). The potential agonist properties of the compound 3e were evaluated on the dermal melanocytes of Xenopus laevis tadpoles. At the concentration of 2.3 nM (5 x K-i), melatonin gave melanophore index value of 1. Similarly to melatonin, 3e was shown to be a potent agonist of the melanosome aggregation.