2-[1-(2-phenylethyl)piperidin-4-ylcarbonyl]-3,4-dihydro-1-hydroxynaphthalene | 156544-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[1-(2-phenylethyl)piperidin-4-ylcarbonyl]-3,4-dihydro-1-hydroxynaphthalene
• 英文别名: (1-Hydroxy-3,4-dihydronaphthalen-2-yl)-[1-(2-phenylethyl)piperidin-4-yl]methanone
• CAS: 156544-93-3
• 化学式: C₂₄H₂₇NO₂
• 分子量: 361.484
• InChiKey: GJSIEHUKEFTEBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[1-(2-phenylethyl)piperidin-4-ylcarbonyl]-3,4-dihydro-1-hydroxynaphthalene 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以55%的产率得到3-[1-(2-phenylethyl)piperidin-4-yl]-4,5-dihydrobenz[g]indazole
  参考文献：
  名称：

  3-(1-Piperazinyl)-4,5-dihydro-1H-benzo[g]indazoles: high affinity ligands for the human dopamine D4 receptor with improved selectivity over ion channels

  摘要：

  3-(4-Piperidinyl)-5-arylpyrazole such as 1, were selective for the cloned human dopamine Dq receptor (hD(4)), but also showed affinity at voltage sensitive calcium, sodium and potassium ion channels. A combination of substituent changes to reduce the basicity of the piperidine nitrogen and conformational restriction to give 4,5-dihydro-1H-benzo[g]indazoles reduced this ion channel affinity at the expense of selectivity for hD4 over other dopamine receptors. Incorporation of piperazine into the 4,5-dihydro-1H-benzo[g]indazoles in place of piperidine gave a novel series of high affinity, selective, orally bioavailable hD(4) ligands, such as 16, with improved selectivity over ion channels. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00028-5
• 作为产物：
  描述：

  1-Boc-4-哌啶甲酸 在 盐酸 、 N,N-二异丙基乙胺 、 N,N'-羰基二咪唑 、 lithium diisopropyl amide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.42h， 生成 2-[1-(2-phenylethyl)piperidin-4-ylcarbonyl]-3,4-dihydro-1-hydroxynaphthalene
  参考文献：
  名称：

  3-(1-Piperazinyl)-4,5-dihydro-1H-benzo[g]indazoles: high affinity ligands for the human dopamine D4 receptor with improved selectivity over ion channels

  摘要：

  3-(4-Piperidinyl)-5-arylpyrazole such as 1, were selective for the cloned human dopamine Dq receptor (hD(4)), but also showed affinity at voltage sensitive calcium, sodium and potassium ion channels. A combination of substituent changes to reduce the basicity of the piperidine nitrogen and conformational restriction to give 4,5-dihydro-1H-benzo[g]indazoles reduced this ion channel affinity at the expense of selectivity for hD4 over other dopamine receptors. Incorporation of piperazine into the 4,5-dihydro-1H-benzo[g]indazoles in place of piperidine gave a novel series of high affinity, selective, orally bioavailable hD(4) ligands, such as 16, with improved selectivity over ion channels. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00028-5

文献信息

• DOPAMINE RECEPTOR SUBTYPE LIGANDS
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0665840A1

  公开（公告）日：1995-08-09
• JPH08502958A
  申请人：——

  公开号：JPH08502958A

  公开（公告）日：1996-04-02
• US5670522A
  申请人：——

  公开号：US5670522A

  公开（公告）日：1997-09-23
• [EN] DOPAMINE RECEPTOR SUBTYPE LIGANDS<br/>[FR] LIGANDS POUR LES SOUS-TYPES DE RECEPTEURS DE DOPAMINE
  申请人：MERCK SHARP & DOHME LIMITED

  公开号：WO1994010162A1

  公开（公告）日：1994-05-11

  (EN) Fused tricyclic heteroaromatic compounds of formula (I) wherein one of X and Y represents nitrogen, and the other of X and Y represents oxygen, sulphur or N-R2; Q represents a substituted five- or six- membered monocyclic heteroaliphatic ring which contains one nitrogen atom as the sole heteroatom and is linked to the five-membered heteroatomic ring containing the moieties X and Y via a carbon atom as well as substituted 3,4-dihydro-1-hydroxy-2-oxomethyl-naphthalene precursors thereto, are ligands for dopamine receptor subtypes within the body and are therefore useful in the treatment of disorders of the dopamine system, in particular schizophrenia.(FR) Des composés hétéroaromatiques tricycliques fusionnés de formule (I), où de X et Y l'un représente azote, et l'autre représente oxygène, soufre ou N-R2, Q représente un cycle hétéroaliphatique monocyclique à cinq ou six membres, contenant un atome d'azote comme le seul hétéroatome et lié au cycle hétéroatomique à cinq branches contenant les fractions X et Y par l'intermédiaire d'un atome de carbone, ainsi que leurs précurseurs substitués de 3,4-dihydro-1-hydroxy-2-oxométhyl-naphtalène, sont des ligands pour les sous-types de récepteurs de dopamine dans le corps, et s'avèrent donc utiles pour le traitement des troubles du système dopamine, et en particulier pour le traitement de la schizophrénie.