cis-2-furanyl((1S*,5R*,7R*)-3-azabicyclo[3.3.0]oct-7-yl)methanone | 1069112-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-2-furanyl((1S*,5R*,7R*)-3-azabicyclo[3.3.0]oct-7-yl)methanone
• CAS: 1069112-61-3
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: NZYPTMVAFUKKKD-OWUUHHOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  42.24
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  tert-butyl (3aS,6aR)-5-[methoxy(methyl)carbamoyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate 在 正丁基锂 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 cis-2-furanyl((1S*,5R*,7R*)-3-azabicyclo[3.3.0]oct-7-yl)methanone
  参考文献：
  名称：

  Novel nicotinic acetylcholine receptor agonists containing carbonyl moiety as a hydrogen bond acceptor

  摘要：

  A novel series of alpha 4 beta 2 nAChR agonists lacking common pyridine or its bioisosteric heterocycle have been disclosed. Essential pharmacophoric elements of the series are exocyclic carbonyl moiety as a hydrogen bond acceptor and secondary amino group within diaza- or azabicyclic scaffold. Computer modeling studies suggested that molecular shape of the ligand also contributes to promotion of agonism. Proof of concept for improving working memory performance in a novel object recognition task has been demonstrated on a representative of the series, 3-propionyl-3,7-diazabicyclo[3.3.0]octane (34). (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.058

文献信息

• SUB-TYPE SELECTIVE AZABICYCLOALKANE DERIVATIVES
  申请人：Hammond Philip S.

  公开号：US20100173968A1

  公开（公告）日：2010-07-08

  Compounds, pharmaceutical compositions including the compounds, and methods of preparation and use thereof are disclosed. The compounds are amide, ketone, and ester compounds prepared from certain azabicycloalkane carboxylic acids. The resulting compounds exhibit selectivity for, and bind with high affinity to, neuronal nicotinic receptors of the α4β2 subtype in the central nervous system (CNS). The compounds and compositions can be used to treat and/or prevent a wide variety of conditions or disorders, such as those disorders characterized by dysfunction of nicotinic cholinergic neurotransmission, including disorders involving neuromodulation of neurotransmitter release, such as dopamine release. CNS disorders, which are characterized by an alteration in normal neurotransmitter release, are another example of disorders that can be treated and/or prevented. The compounds can: (i) alter the number of nicotinic cholinergic receptors of the brain of the patient, (ii) exhibit neuroprotective effects, and (iii) when employed in effective amounts, not result in appreciable adverse side effects (e.g. side effects such as significant increases in blood pressure and heart rate, significant negative effects upon the gastrointestinal tract, and significant effects upon skeletal muscle).

  本文揭示了一些化合物、含有这些化合物的药物组合物及其制备和使用方法。这些化合物是从某些氮杂环烷羧酸制备的酰胺、酮和酯类化合物。由此得到的化合物在中枢神经系统(CNS)中具有选择性和高亲和力地结合到α4β2亚型的神经尼古丁受体上。这些化合物和组合物可用于治疗和/或预防各种疾病或障碍，例如那些以尼古丁胆碱能神经递质功能障碍为特征的疾病，包括涉及神经递质释放的神经调节障碍，如多巴胺释放。中枢神经系统障碍是另一个可以治疗和/或预防的障碍类型，其特征是正常神经递质释放的改变。这些化合物可以：(i)改变患者大脑中尼古丁胆碱能受体的数量，(ii)表现出神经保护作用，以及(iii)在有效剂量下，不会导致明显的不良副作用(例如显著增加血压和心率、对胃肠道的显著负面影响以及对骨骼肌的显著影响)。
• US8198296B2
  申请人：——

  公开号：US8198296B2

  公开（公告）日：2012-06-12
• Novel nicotinic acetylcholine receptor agonists containing carbonyl moiety as a hydrogen bond acceptor
  作者：Anatoly A. Mazurov、David C. Kombo、Srinivasa Akireddy、Srinivasa Murthy、Terry A. Hauser、Kristen G. Jordan、Gregory J. Gatto、Daniel Yohannes

  DOI：10.1016/j.bmcl.2013.04.058

  日期：2013.7

  A novel series of alpha 4 beta 2 nAChR agonists lacking common pyridine or its bioisosteric heterocycle have been disclosed. Essential pharmacophoric elements of the series are exocyclic carbonyl moiety as a hydrogen bond acceptor and secondary amino group within diaza- or azabicyclic scaffold. Computer modeling studies suggested that molecular shape of the ligand also contributes to promotion of agonism. Proof of concept for improving working memory performance in a novel object recognition task has been demonstrated on a representative of the series, 3-propionyl-3,7-diazabicyclo[3.3.0]octane (34). (c) 2013 Elsevier Ltd. All rights reserved.