6-溴己基三乙基溴化铵 | 161097-76-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 6-溴己基三乙基溴化铵
• 英文名称: N,N,N-triethyl-N-bromohexane ammonium bromide
• 英文别名: 6-bromohexyltriethylammonium bromide；6-bromohexyl(triethyl)azanium;bromide
• CAS: 161097-76-3
• 化学式: Br*C₁₂H₂₇BrN
• 分子量: 345.161
• InChiKey: SUPZNVBPHMFWPG-UHFFFAOYSA-M

物化性质

• 溶解度：
  可溶于乙腈、二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[3-(二甲氨基)丙基]异吲哚-1,3-二酮 、 6-溴己基三乙基溴化铵 以 乙醇 为溶剂， 反应 20.0h， 以36%的产率得到N,N,N-triethyl-N',N'-dimethyl-N'-(3-phthalimidopropyl)-N,N'-hexane-1,6-diyl-ammonium dibromide
  参考文献：
  名称：

  Allosteric effect on muscarinic M2-receptors of derivatives of the alkane-bis-ammonium compound W84. Comparison with bispyridinium-type allosteric modulators

  摘要：

  The symmetrically shaped W84 = N,N,N',N'-tetramethyl-N,N'-bis-(3-phthalimido-propyl)-N,N'-hexane-1,6-diyl-bis-ammonium dibromide is a potent allosteric stabilizer of antagonist-binding to cardiac muscarinic M(2)-receptors. The ability of unilaterally shortened W84 derivatives to allosterically retard the dissociation of [H-3]N-methylscopolamine ([H-3]NMS) from M(2)-receptors was determined in porcine cardiac membranes (3 mM MgHPO4, 50 mM TrisHCl, pH 7.3, 37 degrees C). Shortening was accompanied by a reduction of the allosteric activity. For instance, W84 prolonged the half-life of [H-3]NMS dissociation (control t(1/2) = 2.0 min) by a factor of 2 at a concentration of EC(50) = 1.3 mu M, whereas a derivative unilaterally lacking phthalimidopropyl- dimethylammonium was 40-fold less potent. It is concluded that the whole W84 molecule interacts with the allosteric site of the receptor. The structure-activity relationships found with this series of agents did not parallel findings made previously with similarly modified derivatives of the bispyridinium compound DUO 3, (E,E)-1,1'-(1,3-propanediyl)-bis[4-[[(2,6-dichlorobenzoxyl)imino]methyl]pyridinium]dibromide, despite considerable similarity with respect to molecular shape and charge distribution.

  DOI：

  10.1016/0223-5234(94)90194-5

文献信息

• Search for Selective Glua1 Ampa Receptor Antagonists in a Series of Dicationic Compounds
  作者：V. E. Gmiro、A. S. Zhigulin

  DOI：10.1007/s11094-022-02635-w

  日期：2022.6

  Homologous series of dicationic derivatives based on adamantyl and phenylcyclohexyl fragments in which the cationic groups and the distance between them were varied by using hydrocarbon chains five or six methylene units in length were synthesized. The ability of the dications to block open channels of NMDA and AMPA glutamate receptors was investigated. Pyramidal neurons isolated from the hippocampal CA1 zone were used to study the NMDA channels. Giant cholinergic interneurons of striatum were used in studies of AMPA receptors missing GluA2 subunits. An investigation of the structure—activity relationship of the dications revealed five compounds (IEM-2131, -2132, -2133, -2041, -2297) that surpassed the reference GluA1 AMPA antagonist IEM-1460 in terms of GluA1 AMPA selectivity. IEM-2131, which was an order of magnitude more active than IEM-1460 in AMPA-blocking activity (IC50 = 0.29 and 3 μM, respectively), showed the maximum AMPA activity and selectivity and had five times better AMPA selectivity (101- and 500-fold, respectively). The clinical prospects of the new GluA1 AMPA blockers were discussed.

  基于金刚烷和苯基环己烷片段，通过合成长度为5或6个亚甲基单元的烃链，我们获得了阳离子基团及其间距各异的同源二阳离子衍生物系列。我们研究了二阳离子阻断NMDA和AMPA谷氨酸受体开放通道的能力。从海马CA1区分离出的锥体神经元被用于研究NMDA通道。纹状体中的巨大型胆碱能中间神经元被用于研究缺失GluA2亚基的AMPA受体。对二阳离子的结构-活性关系的研究表明，有五种化合物（IEM-2131、-2132、-2133、-2041、-2297）在GluA1 AMPA选择性方面超过了参考GluA1 AMPA拮抗剂IEM-1460。IEM-2131在AMPA阻断活性（IC50分别为0.29和3μM）方面比IEM-1460高出一个数量级，显示出最大的AMPA活性和选择性，并且AMPA选择性提高了5倍（分别为101倍和500倍）。我们讨论了新型GluA1 AMPA阻断剂的临床前景。
• 一种金属卡宾光诊疗剂的合成方法
  申请人：西北大学

  公开号：CN117447494A

  公开（公告）日：2024-01-26

  本发明属于药物化学合成领域，具体涉及一种金属卡宾光诊疗剂的合成方法。金属卡宾光诊疗剂具有如式(I)或式(II)所示的结构；#imgabs0#式(I)；#imgabs1#式(II)；其中，X为H、Cl、Br或Ome，M为Ag、Au或Cu，Y为Cl、Br或I，R为碳原子数为1‑12的烷基、#imgabs2#、#imgabs3#或#imgabs4#。金属卡宾光诊疗剂中氮杂环卡宾的引入拉近了两分子苝酰亚胺之间的距离，增强了分子内相互作用，强化了隙间窜越及分子内电荷转移，导致非辐射弛豫提高，最终大大提高了所得光诊疗剂的光热及光动力性能。并且该方法具有工艺稳定简捷，产率高，稳定性好等特点。可通过简单的更换氮杂环卡宾类型得到不同电子特性和光转化性的光诊疗剂。并且合成方法具有普适性较好，产物易于分离，收率高等特点。