3-Pyrrolyl methylene anabaseine | 1122531-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-Pyrrolyl methylene anabaseine
• 英文别名: (3e)-3-(1h-Pyrrol-3-Ylmethylidene)-3,4,5,6-Tetrahydro-2,3'-Bipyridine；3-[(5E)-5-(1H-pyrrol-3-ylmethylidene)-3,4-dihydro-2H-pyridin-6-yl]pyridine
• CAS: 1122531-47-8
• 化学式: C₁₅H₁₅N₃
• 分子量: 237.304
• InChiKey: LCDAAPCYCXHGRV-UKTHLTGXSA-N

物化性质

• 沸点：
  440.6±45.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  sodium (1-((diethylamino)methyl)-2-oxopiperidin-3-ylidene)(pyridin-3-yl)methanolate 在 盐酸 、 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 96.0h， 生成 3-Pyrrolyl methylene anabaseine
  参考文献：
  名称：

  Synthesis of H-bonding probes of α7 nAChR agonist selectivity

  摘要：

  The alpha 7 subtype of the nicotinic acetylcholine receptor (nAChR) is the target of studies aimed at identifying features that will lead to the development of selective therapeutics. Five arylidine anabaseines, three with pyridine rings and two with the pyrrole rings, were synthesized in 35-65% yield via aldol condensation. The compounds are homologs of benzylidine anabaseine and were chosen for synthesis because they provide either a hydrogen bond acceptor (pyridines) or hydrogen bond donor (pyrroles) that may interact with the receptor within the benzylidine selectivity motif. Initial analysis of the new compounds at 100 mu M concentration reveal that the two pyrrole anabaseines are good partial agonists of the alpha 7 nAChR, having 40% of the efficacy of ACh, efficacy comparable to 4OH-GTS-21, and dramatically enhanced efficacy relative to the 2- and 4-pyridinyl compounds. The pyrrole compounds were confirmed to be alpha 7 selective, displaying preference for this receptor over muscle and heteromeric neuronal receptor subtypes. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.044

文献信息

• [EN] ANABASEINE DERIVATIVES USEFUL IN THE TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] DERIVES D'ANABASEINE UTILES POUR LE TRAITEMENT DE MALADIES NEURODEGENERATIVES
  申请人：MEMORY PHARM CORP

  公开号：WO2004019943A1

  公开（公告）日：2004-03-11

  The compounds of the present invention are of formula (I): wherein A, R3, R4 is as defined herein, are useful as ligands for nicotinic receptors.

  本发明的化合物的化学式为（I）：其中A、R3、R4如本文所定义，可用作尼古丁受体的配体。
• Heterocyclic compounds, methods for the preparation thereof, and uses thereof
  申请人：MEMORY PHARMACEUTICALS CORP.

  公开号：US20040229868A1

  公开（公告）日：2004-11-18

  The compounds of the present invention are of formula I: 1 wherein A, R 3 , R 4 is as defined herein, are useful as ligands for nicotinic receptors.

  本发明的化合物的化学式为I:1，其中A、R3、R4如本文所定义，可用作尼古丁受体的配体。
• HETEROCYCLIC COMPOUNDS, METHODS FOR THE PREPARATION THEREOF, AND USES THEREOF
  申请人：Herbert Brian

  公开号：US20100173891A1

  公开（公告）日：2010-07-08

  The compounds of the present invention are of formula I: wherein A, R 3 , R 4 is as defined herein, are useful as ligands for nicotinic receptors.

  本发明的化合物为公式I：其中A、R3、R4如此处所定义，可用作尼古丁受体的配体。
• Anabaseine derivatives useful in the treatment of neurodegenerative diseases
  申请人：Memory Pharmaceuticals Corporation

  公开号：EP2298758A1

  公开（公告）日：2011-03-23

  The compounds of the present invention are of formula (I): wherein A, R3, R4 is as defined herein, are useful as ligands for nicotinic receptors.

  本发明的化合物如式 (I)：其中 A、R3、R4 如本文所定义，可用作烟碱受体的配体。
• Anabaseine derivatives useful in the treatment of neurodegeneratives diseases
  申请人：Memory Pharmaceuticals Corporation

  公开号：EP2305664A1

  公开（公告）日：2011-04-06

  The compounds of the present invention are of formula (I): wherein A, R3, R4 is as defined herein, are useful as ligands for nicotinic receptors.

  本发明的化合物如式 (I)：其中 A、R3、R4 如本文所定义，可用作烟碱受体的配体。