Isoquinolinium, 2,2'-(1,6-hexanediyl)bis-, diiodide | 122802-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: Isoquinolinium, 2,2'-(1,6-hexanediyl)bis-, diiodide
• 英文别名: 1,6-bis(isoquinolinium)hexane diiodide；bIQHxI；2,2'-hexanediyl-bis-isoquinolinium; diiodide；2,2'-Hexandiyl-bis-isochinolinium; Dijodid；N,N'-hexane-1,6-diyl-bis-isoquinolinium diiodide
• CAS: 122802-43-1
• 化学式: C₂₄H₂₆N₂*2I
• 分子量: 596.293
• InChiKey: SOLQEUJPFDVAGC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  异喹啉 、 1,6-二碘己烷 以 N,N-二甲基甲酰胺 为溶剂， 以31%的产率得到Isoquinolinium, 2,2'-(1,6-hexanediyl)bis-, diiodide
  参考文献：
  名称：

  双（异喹啉鎓）烷烃二甲双胍在水溶液中的葫芦[7]脲络合

  摘要：

  一系列 1,n-双（异喹啉鎓）烷烃 (Iq(CH2)nIq2+, n = 2, 4, 5, 6, 8, 9, 10 和 12) 的 1:1 和 2:1 主客体络合, 和 Iq(p-二甲苯)Iq2+) 由葫芦[7] uril (CB[7]) 在水溶液中的 1H NMR 光谱和 ESI 质谱进行了研究。第一个 CB[7] 的结合位点取决于中心连接基团的性质，当 n = 6-10 时对二甲苯基团或多亚甲基链的封装。 较短 (n = 2-5)或更长 (n = 12) 链，第一个 CB[7] 结合在异喹啉基团上。使用第二个 CB[7]，中心基团的结合被放弃，转而采用 CB[7] 宿主封装两个阳离子异喹啉末端。1:1 和 2:1 的主客体稳定性常数与结合模式和中央接头的性质有关，

  DOI：

  10.1080/10610278.2013.842645

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
• Austin et al., Journal of the Chemical Society, 1958, p. 1489,1497
  作者：Austin et al.

  DOI：——

  日期：——
• 3D-QSAR study of bis-azaaromatic quaternary ammonium analogs at the blood–brain barrier choline transporter
  作者：Werner J. Geldenhuys、Paul R. Lockman、Tiffany H. Nguyen、Cornelis J. Van der Schyf、Peter A. Crooks、Linda P. Dwoskin、David D. Allen

  DOI：10.1016/j.bmc.2005.04.020

  日期：2005.7

  Previously, we have developed 3D-QSAR models of the blood-brain barrier (BBB) choline transporter, a transport system that may have utility as a vector for central nervous system drug delivery. In this study, we extended the model by evaluating five bis-azaaromatic quaternary ammonium compounds for their affinity for the choline binding site on the BBB-choline transporter. The compounds, and their affinities for the transporter, were then incorporated into our existing molecular model, in order to update our knowledge on the molecular recognition factors associated with interaction of ligands at the choline binding site. The current compounds are structurally related to previous substrates that we have evaluated, but offer additional three dimensional aspects compared to the series of compounds previously utilized to define the original models. The compounds showed good affinity for the BBB-choline transporter, exhibiting inhibition constants ranging from 10 to 68 mu M, as determined by the in situ rat brain perfusion method. Comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) methods were used to build the new 3D QSAR models. When the new bis-azaaromatic quaternary ammonium compounds were included in the model, the best cross-validated CoMFA q(2) was found to be 0.536 and the non-cross-validated r(2) was 0.818. CoMSIA hydrophobic cross-validated q(2) was 0.506 and the non-cross-validated r(2) was 0.804. This new model was able to better predict BBB-choline transporter affinity of hemicholinium-3 (predicted 65 mu M, actual 54 mu M), when compared to an earlier model (predicted 316 mu M). (c) 2005 Elsevier Ltd. All rights reserved.