6-(pyrrolidin-1-ylmethyl)naphthalen-2-ylamine | 372149-65-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(pyrrolidin-1-ylmethyl)naphthalen-2-ylamine
• 英文别名: 6-(1-pyrrolidinylmethyl)naphthalene-2-amine；6-(Pyrrolidin-1-ylmethyl)naphthalen-2-amine
• CAS: 372149-65-0
• 化学式: C₁₅H₁₈N₂
• 分子量: 226.321
• InChiKey: XDACWJTYIVEDBG-UHFFFAOYSA-N

物化性质

• 沸点：
  395.5±17.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(pyrrolidin-1-ylmethyl)naphthalen-2-ylamine 生成 4-Methylphenyl-N-[6-(1-pyrrolidinylmethyl)-2-naphthyl]-1-piperidinecarboxamide
  参考文献：
  名称：

  MELANIN CONCENTRATING HORMONE ANTAGONISTS

  摘要：

  公开号：

  EP1285651B1
• 作为产物：
  描述：

  2,6-萘二羧酸二甲酯 在 lithium aluminium tetrahydride 、 叠氮磷酸二苯酯 、 potassium carbonate 、 三乙胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 17.5h， 生成 6-(pyrrolidin-1-ylmethyl)naphthalen-2-ylamine
  参考文献：
  名称：

  Melanin-Concentrating Hormone Receptor 1 Antagonists. Synthesis and Structure–Activity Relationships of Novel 3-(Aminomethyl)quinolines

  摘要：

  It was found that 3-(aminomethyl)quinoline derivatives showed high binding affinities for melanin-concentrating hormone receptor 1 (MCHR1) with reduced affinity for serotonin receptor 2c (5-HT2c) when the dihydronaphthalene nucleus of compound 1 (human MCHR1, IC50 = 1.9 nM; human 5-HT2c receptor, IC50 = 0.53 nM) was replaced by other bicyclic core scaffolds. Among the synthesized compounds, 8-methylquinoline derivative 5v especially showed high binding affinity (IC50 = 0.54 nM), potent in vitro antagonistic activity (IC50 = 2.8 nM) for MCHR1, and negligible affinity for 5-HT2c receptor (IC50 > 1000 nM). Oral administration of 5v significantly and dose-dependently suppressed nocturnal food intake in diet-induced obese rats and did not affect food intake in MCHR1-deficient mice. These results and rat pharmacokinetic study findings suggested that compound 5v is a highly potent, orally bioavailable, and centrally acting nonpeptide MCHR1 antagonist.

  DOI：

  10.1021/jm201596h

文献信息

• Melanin-concentrating hormone antagonist
  申请人：——

  公开号：US20040077628A1

  公开（公告）日：2004-04-22

  A melanin-concentrating hormone antagonist comprising a compound of the formula (I): 1 wherein Ar 1 is a cyclic group which may be substituted; X and Y are the same or different and are a spacer having a main chain of 1 to 6 atoms; Ar is a condensed polycyclic aromatic ring which may be substituted; R 1 and R 2 are the same or different and are hydrogen atom or a hydrocarbon group which may be substituted; or R 1 and R 2 , together with the adjacent nitrogen atom, may form a nitrogen-containing heterocyclic ring which may be substituted; or R 2 , together with the adjacent nitrogen atom and Y, may form a nitrogen-containing heterocyclic ring which may be substituted; or R 2 , together with the adjacent nitrogen atom, Y and Ar, may form a condensed ring; or a salt thereof is useful as an agent for preventing or treating obesity, etc.

  一种黑色素浓集激素拮抗剂，包括化合物(I)的一种，其中Ar1是一个可以被取代的环状基团；X和Y相同或不同，是具有1至6个原子的主链间隔物；Ar是一个可以被取代的紧凑多环芳香环；R1和R2相同或不同，是氢原子或可以被取代的碳氢基团；或者R1和R2与相邻的氮原子一起可以形成一个可以被取代的含氮杂环；或者R2与相邻的氮原子和Y一起可以形成一个可以被取代的含氮杂环；或者R2与相邻的氮原子、Y和Ar一起可以形成一个紧凑环；或其盐，可用作预防或治疗肥胖等药物。
• US6930185B2
  申请人：——

  公开号：US6930185B2

  公开（公告）日：2005-08-16
• [EN] HETEROCYCLIC MCHR1 ANTAGONISTS<br/>[FR] ANTAGONISTES HETEROCYCLIQUES DE MCHR1
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2004092181A9

  公开（公告）日：2005-01-27

  [EN] This invention relates to novel heterocycles which are antagonists at the melanin-concentrating hormone receptor 1 (MCHR1), also referred to as 11CBy, to pharmaceutical compositions containing them, to processes for their preparation, and to their use in medicines. Compounds of the invention have formula (I).
  [FR] L'invention concerne des dérivés de benzopyrane substitués, des stéréoisomères et des sels pharmaceutiquement acceptables desdits composés, ainsi que des procédés appropriés pour les préparer. Les composés de la présente invention s'utilisent comme agonistes du récepteur beta des oestrogènes. De tels agonistes s'utilisent dans le traitement d'affections induites par le récepteur beta des oestrogènes, telles que le cancer de la prostate ou l'hyperplasie prostatique bénigne (HPB).
• Melanin-Concentrating Hormone Receptor 1 Antagonists. Synthesis and Structure–Activity Relationships of Novel 3-(Aminomethyl)quinolines
  作者：Makoto Kamata、Toshiro Yamashita、Toshihiro Imaeda、Toshio Tanaka、Shinichi Masada、Masahiro Kamaura、Shizuo Kasai、Ryoma Hara、Shigekazu Sasaki、Shiro Takekawa、Asano Asami、Tomoko Kaisho、Nobuhiro Suzuki、Shuntaro Ashina、Hitomi Ogino、Yoshihide Nakano、Yasutaka Nagisa、Koki Kato、Kaneyoshi Kato、Yuji Ishihara

  DOI：10.1021/jm201596h

  日期：2012.3.8

  It was found that 3-(aminomethyl)quinoline derivatives showed high binding affinities for melanin-concentrating hormone receptor 1 (MCHR1) with reduced affinity for serotonin receptor 2c (5-HT2c) when the dihydronaphthalene nucleus of compound 1 (human MCHR1, IC50 = 1.9 nM; human 5-HT2c receptor, IC50 = 0.53 nM) was replaced by other bicyclic core scaffolds. Among the synthesized compounds, 8-methylquinoline derivative 5v especially showed high binding affinity (IC50 = 0.54 nM), potent in vitro antagonistic activity (IC50 = 2.8 nM) for MCHR1, and negligible affinity for 5-HT2c receptor (IC50 > 1000 nM). Oral administration of 5v significantly and dose-dependently suppressed nocturnal food intake in diet-induced obese rats and did not affect food intake in MCHR1-deficient mice. These results and rat pharmacokinetic study findings suggested that compound 5v is a highly potent, orally bioavailable, and centrally acting nonpeptide MCHR1 antagonist.
• MELANIN CONCENTRATING HORMONE ANTAGONISTS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1285651B1

  公开（公告）日：2010-09-01