9-phenyl-1,2,3,4,5,6-hexahydro-1,5-methano-pyridino[1,2-a]diazocin-8-one [3-phenyl-cytisine]

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 羽扇豆生物碱
• 英文名称: 9-phenyl-1,2,3,4,5,6-hexahydro-1,5-methano-pyridino[1,2-a]diazocin-8-one [3-phenyl-cytisine]
• 英文别名: 9-phenyl-1,2,3,4,5,6-hexahydro-1,5-methano-pyridino[1,2-a]diazocin-8-one；(1R,9S)-5-phenyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: MGQATKFFMYTJKY-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  cytisine 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 5.17h， 生成 9-phenyl-1,2,3,4,5,6-hexahydro-1,5-methano-pyridino[1,2-a]diazocin-8-one [3-phenyl-cytisine]
  参考文献：
  名称：

  WO2007/100430

  摘要：

  公开号：

文献信息

• Cytisine and Acetylcholine Analogs and Methods of Treating Mood Disorders
  申请人：Picciotto Marina

  公开号：US20090318491A1

  公开（公告）日：2009-12-24

  The present invention relates to compounds which are derivatives of cytisine or acetylcholine which exhibit activity as agonists, partial agonists or antagonists of nicotinic acetylcholine receptors and may be used in modulating these receptors and in treating mood disorders in patients in need of therapy.

  本发明涉及一种衍生自细胞毒素或乙酰胆碱的化合物，其表现为尼古丁乙酰胆碱受体的激动剂、部分激动剂或拮抗剂，并可用于调节这些受体和治疗需要治疗的情绪障碍患者。
• The 3,7-diazabicyclo[3.3.1]nonane scaffold for subtype selective nicotinic acetylcholine receptor ligands. Part 2: Carboxamide derivatives with different spacer motifs
  作者：Christoph Eibl、Lenka Munoz、Isabelle Tomassoli、Clare Stokes、Roger L. Papke、Daniela Gündisch

  DOI：10.1016/j.bmc.2013.09.060

  日期：2013.12

  3,7-Diazabicyclo[3.3.1]nonane (bispidine) based nicotinic acetylcholine receptor (nAChR) ligands have been synthesized and evaluated for nAChRs interaction. Diverse spacer motifs were incorporated between the hydrogen bond acceptor (HBA) part and a variety of substituted (hetero)aryl moieties. Bispidine carboxamides bearing spacer motifs often showed high affinity in the low nanomolar range and selectivity for the alpha 4 beta 2* nAChR. Compounds 15, 25, and 47 with K-i values of about 1 nM displayed the highest affinities for alpha 4 beta 2* nAChR. All evaluated compounds are partial agonists or antagonists at alpha 4 beta 2*, with reduced or no effects on alpha 3 beta 4* with the exception of compound 15 (agonist), and reduced or no effect at alpha 7 and muscle subtypes. (C) 2013 Elsevier Ltd. All rights reserved.
• CYTISINE AND ACETYLCHOLINE ANALOGS AND METHODS OF TREATING MOOD DISORDERS
  申请人：Yale University

  公开号：EP1976519A2

  公开（公告）日：2008-10-08
• [EN] CYTISINE AND ACETYLCHOLINE ANALOGS AND METHODS OF TREATING MOOD DISORDERS<br/>[FR] ANALOGUES DE CYSTISINE ET D'ACÉTYLCHOLINE ET PROCÉDÉS DE TRAITEMENT DES TROUBLES DE L'HUMEUR
  申请人：UNIV YALE

  公开号：WO2007100430A2

  公开（公告）日：2007-09-07

  [EN] The present invention relates to compounds which are derivatives of cytisine or acetylcholine which exhibit activity as agonists, partial agonists or antagonists of nicotinic acetylcholine receptors and may be used in modulating these receptors and in treating mood disorders in patients in need of therapy.
  [FR] La présente invention concerne des composés qui sont des dérivés de cystisine ou d'acétylcholine qui présentent une activité d'agonistes, d'agonistes partiels ou d'antagonistes des récepteurs d'acétylcholine nicotinique et qui peuvent être utilisés pour moduler ces récepteurs et pour traiter des troubles de l'humeur chez des patients nécessitant une thérapie.