2-丙烯酸聚合乙烯基苯,钾盐 | 73870-27-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-丙烯酸聚合乙烯基苯,钾盐
• 英文名称: Lepidyl(triphenyl)phosphoniumbromid
• 英文别名: Triphenyl[(quinolin-4-yl)methyl]phosphanium bromide；triphenyl(quinolin-4-ylmethyl)phosphanium;bromide
• CAS: 73870-27-6
• 化学式: Br*C₂₈H₂₃NP
• 分子量: 484.375
• InChiKey: TWTAIFYJTNPARK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-丙烯酸聚合乙烯基苯,钾盐 在 盐酸 、 palladium 10% on activated carbon 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 4-[2-[(2R,6S)-6-(2-quinolin-4-ylethyl)piperidin-2-yl]ethyl]quinoline
  参考文献：
  名称：

  Quinolyl analogues of norlobelane: Novel potent inhibitors of [3H]dihydrotetrabenazine binding and [3H]dopamine uptake at the vesicular monoamine transporter-2

  摘要：

  We have previously shown that quinolyl moieties are attractive structural replacements for the phenyl groups in lobelane. These quinolyl analogues had improved water-solubility over lobelane and retained the potent vesicular monoamine transporter-2 (VMAT-2) inhibitory properties of the parent compound, with quinlobelane (4) exhibiting potent inhibition of uptake at VMAT-2 (K-i = 51 nM). However, the VMAT-2 inhibitory properties of quinolyl analogues of norlobelane, which is equipotent with lobeline as an inhibitor of [H-3] dopamine (DA) uptake at VMAT-2, have not been reported. In the current communication, we describe the synthesis of some novel des-methyl quinolyl analogues of lobelane that exhibit greater affinity (K-i = 178-647 nM) for the dihydrotetrabenazine binding site located on VMAT-2 compared with lobelane (K-i = 970 nM), norlobelane (K-i = 2310 nM) and quinlobelane (K-i = 2640 nM). The most potent compounds, 14 and 15, also exhibited inhibition of [H-3] DA uptake at VMAT-2 (K-i = 42 nM) which was comparable to both lobelane (K-i = 45 nM) and norlobelane (K-i = 43 nM). Results reveal that binding affinity at VMAT-2 serves as an accurate predictor of inhibition of the function of VMAT-2 for the majority of these analogues. These novel analogues are under consideration for further development as treatments for methamphetamine abuse. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.105
• 作为产物：
  描述：

  4-溴甲基喹啉 、 三苯基膦 以 苯 为溶剂， 反应 24.0h， 以62%的产率得到2-丙烯酸聚合乙烯基苯,钾盐
  参考文献：
  名称：

  Carsky, Petr; Huenig, Siegfried; Stemmler, Ingo, Liebigs Annalen der Chemie, 1980, # 2, p. 291 - 304

  摘要：

  DOI：

文献信息

• Carsky, Petr; Huenig, Siegfried; Stemmler, Ingo, Liebigs Annalen der Chemie, 1980, # 2, p. 291 - 304
  作者：Carsky, Petr、Huenig, Siegfried、Stemmler, Ingo、Scheutzow, Dieter

  DOI：——

  日期：——
• Quinolyl analogues of norlobelane: Novel potent inhibitors of [3H]dihydrotetrabenazine binding and [3H]dopamine uptake at the vesicular monoamine transporter-2
  作者：Derong Ding、Justin R. Nickell、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1016/j.bmcl.2015.04.105

  日期：2015.7

  We have previously shown that quinolyl moieties are attractive structural replacements for the phenyl groups in lobelane. These quinolyl analogues had improved water-solubility over lobelane and retained the potent vesicular monoamine transporter-2 (VMAT-2) inhibitory properties of the parent compound, with quinlobelane (4) exhibiting potent inhibition of uptake at VMAT-2 (K-i = 51 nM). However, the VMAT-2 inhibitory properties of quinolyl analogues of norlobelane, which is equipotent with lobeline as an inhibitor of [H-3] dopamine (DA) uptake at VMAT-2, have not been reported. In the current communication, we describe the synthesis of some novel des-methyl quinolyl analogues of lobelane that exhibit greater affinity (K-i = 178-647 nM) for the dihydrotetrabenazine binding site located on VMAT-2 compared with lobelane (K-i = 970 nM), norlobelane (K-i = 2310 nM) and quinlobelane (K-i = 2640 nM). The most potent compounds, 14 and 15, also exhibited inhibition of [H-3] DA uptake at VMAT-2 (K-i = 42 nM) which was comparable to both lobelane (K-i = 45 nM) and norlobelane (K-i = 43 nM). Results reveal that binding affinity at VMAT-2 serves as an accurate predictor of inhibition of the function of VMAT-2 for the majority of these analogues. These novel analogues are under consideration for further development as treatments for methamphetamine abuse. (C) 2015 Elsevier Ltd. All rights reserved.