[1,9-bis(1-pyridinium)nonane]*2Br | 24318-08-9

• 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: [1,9-bis(1-pyridinium)nonane]*2Br
• 英文别名: 1,9-bis(pyridinium)-nonane dibromide；N,N'-nonane-1,9-diyl-bis-pyridinium dibromide
• CAS: 24318-08-9
• 化学式: 2Br*C₁₉H₂₈N₂
• 分子量: 444.253
• InChiKey: AWYVDGXUKDTIFF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  7.76
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  吡啶 、 1,9-二溴壬烷 生成 [1,9-bis(1-pyridinium)nonane]*2Br
  参考文献：
  名称：

  1，ω-双（吡啶）烷烃模板指导的多金属氧酸盐的构建和异构转化†

  摘要：

  十种新型的无机-有机杂多金属氧酸盐，即[1,3-双（吡啶）丙烷] 2 [ α- Mo 8 O 26 ]（1），[1,4-双（吡啶）丁烷] 2 [1D-Mo 8 O 26 ]（2），[1,5-双（吡啶）戊烷] 2 [ θ- Mo 8 O 26 ]（3），[1,6-双（吡啶）正己烷] 2 [1D-Mo 8 O 26 ]（4），[1,7-双（吡啶）庚烷] 2 [ β- Mo 8 O 26]（5），[1,8-双（吡啶）辛烷] 2 [ θ- Mo 8 O 26 ]（6），[1,9-双（吡啶）壬烷] 2 [（α + β）-Mo 8 ø 26 ]（7），[1,10-二（吡啶鎓）癸烷] 2 [ β -Mo 8 ø 26 ]（8），[1,11双（吡啶）十一烷] 2 [ β -Mo 8 Ô 26 ]（9），[1,12-双（吡啶）十二烷] 2 [ γ-Mo 8 O 26 ]（10），（方案1）是在水热反应条件下

  DOI：

  10.1039/c1ce05245d

文献信息

• bis-Azaaromatic quaternary ammonium analogues: ligands for α4β2* and α7* subtypes of neuronal nicotinic receptors
  作者：Joshua T Ayers、Linda P Dwoskin、A.Gabriela Deaciuc、Vladimir P Grinevich、Jun Zhu、Peter A Crooks

  DOI：10.1016/s0960-894x(02)00687-x

  日期：2002.11

  A series of bis-nicotinium, bis-pyridinium, bis-picolinium, bis-quinoliniurn and bis-isoquinolinium compounds was evaluated for their binding affinity at nicotinic acetylcholine receptors (nAChRs) using rat brain membranes. N,N'-Decane-1,12-diyl-bis-nicotinium diiodide (bND1) exhibited the highest affinity for [H-3]nicotine binding sites (K-i = 330 nM), but did not inhibit [H-3]methyllycaconitine binding (K-i > 100 muM), indicative of an interaction with alpha4beta2*, but not alpha7* receptor subtypes, respectively. Also, bND1 inhibited (IC50 = 3.76 muM) nicotine-evoked Rb-86(+) efflux from rat thalamic synaptosomes, indicating antagonist activity at alpha4beta2* nAChRs. N,N'-Dodecane-1,12-diyl-bis-quinolinium dibromide (bQDDB) exhibited highest affinity for [H-3]methyllycaconitine binding sites (K-i = 1.61 muM), but did not inhibit [H-3]nicotine binding (K-i > 100 muM), demonstrating an interaction with alpha7*, but not alpha4beta2* nAChRs. Thus, variation of N-n-alkyl chain length together with structural modification of the azaaromatic quaternary ammonium moiety afforded selective antagonists for the alpha4beta2* nAChR subtype, as well as ligands with selectivity at a7* nAChRs. (C) 2002 Elsevier Science Ltd. All rights reserved.
• [EN] BIS-PYRIDINO CONTAINING COMPOUNDS FOR USE IN THE TREATMENT OF CNS PATHOLOGIES<br/>[FR] COMPOSES CONTENANT DES BIS-PYRIDINO UTILISES DANS LE TRAITEMENT DE PATHOLOGIES DU SNC
  申请人：UNIV KENTUCKY RES FOUND

  公开号：WO2005066129A3

  公开（公告）日：2005-10-20
• Preparation and in vitro screening of symmetrical bispyridinium cholinesterase inhibitors bearing different connecting linkage—initial study for Myasthenia gravis implications
  作者：Kamil Musilek、Marketa Komloova、Vlasta Zavadova、Ondrej Holas、Martina Hrabinova、Miroslav Pohanka、Vlastimil Dohnal、Florian Nachon、Martin Dolezal、Kamil Kuca、Young-Sik Jung

  DOI：10.1016/j.bmcl.2010.01.034

  日期：2010.3

  Reversible inhibitors (e. g., pyridostigmine bromide, neostigmine bromide) of carbamate origin are used in the early treatment of Myasthenia gravis (MG) to block acetylcholinesterase (AChE) native function and conserve efficient amount of acetylcholine for decreasing number of nicotinic receptors. Carbamate inhibitors are known for many undesirable side effects related to the reversible inhibition of AChE. In contrast, this paper describes 20 newly prepared bispyridinium inhibitors of potential concern for MG. Although some compounds from this series have been known before, they were not assayed for cholinesterase inhibition yet.The newly prepared compounds were evaluated in vitro on human erythrocyte AChE and human plasmatic butyrylcholinesterase (BChE). Their inhibitory ability was expressed as IC(50) and compared to standard carbamate drugs. Three compounds presented promising inhibition (in mu M range) of both enzymes in vitro similar to the used standards. The novel inhibitors did not present selectivity between AChE and BChE. Two newly prepared compounds were chosen for docking studies and confirmed apparent pi-pi or pi-cationic interactions aside enzyme's catalytic sites. The kinetics assay confirmed non-competitive inhibition of AChE by two best newly prepared compounds. (C) 2010 Elsevier Ltd. All rights reserved.