1-(2-methoxyphenyl)-4-(2-(2-(6-bromo)-N-oxopyridinylamino)ethyl)piperazine | 345966-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(2-methoxyphenyl)-4-(2-(2-(6-bromo)-N-oxopyridinylamino)ethyl)piperazine
• 英文别名: 1-(2-methoxyphenyl)-4-(2-(2-(6-bromo)aminopyridinyl-N-oxide)ethyl)piperazine
• CAS: 345966-38-3
• 化学式: C₁₈H₂₃BrN₄O₂
• 分子量: 407.31
• InChiKey: OWFOYBBHKOMJQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  54.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(2-methoxyphenyl)-4-(2-(2-(6-bromo)-N-oxopyridinylamino)ethyl)piperazine 在 铁粉 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 34.0h， 生成 N-(2-(1-(4-(2-methoxyphenyl)piperazinyl)ethyl))-N-(2-(6-bromo)pyridinyl)cyclohexane carboxamide
  参考文献：
  名称：

  Short and efficient syntheses of analogues of way-100635: new and potent 5-HT1A receptor antagonists

  摘要：

  Simple syntheses of four new and potent analogues of the 5-HT1A receptor ligand, WAY-100635 are described, namely the 6-(pyridinyl)-bromo-, the 6-(pyridinyl)-fluoro-, the pyrimidine- and the 5-(pyridinyl)-bromo-analogues. The first three analogues were obtained by aromatic nucleophilic substitution of the 2,6-dihalogenopyridine (activated or not as an N-oxide) or of the 2-chloropyrimidine with the corresponding amine nucleophile as a key step. The fourth analogue, the 5-(pyridinyl)-bromo-analogue, was synthesized from the 2-amino-5-bromopyridine via a progressive elongation of the skeleton. The four compounds described are all full antagonists and show good in vitro binding affinities (K-i). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00287-x
• 作为产物：
  描述：

  2,6-二溴吡啶 在 双氧水 、 三乙胺 、 三氟乙酸 作用下， 以 正丁醇 为溶剂， 反应 37.0h， 生成 1-(2-methoxyphenyl)-4-(2-(2-(6-bromo)-N-oxopyridinylamino)ethyl)piperazine
  参考文献：
  名称：

  Short and efficient syntheses of analogues of way-100635: new and potent 5-HT1A receptor antagonists

  摘要：

  Simple syntheses of four new and potent analogues of the 5-HT1A receptor ligand, WAY-100635 are described, namely the 6-(pyridinyl)-bromo-, the 6-(pyridinyl)-fluoro-, the pyrimidine- and the 5-(pyridinyl)-bromo-analogues. The first three analogues were obtained by aromatic nucleophilic substitution of the 2,6-dihalogenopyridine (activated or not as an N-oxide) or of the 2-chloropyrimidine with the corresponding amine nucleophile as a key step. The fourth analogue, the 5-(pyridinyl)-bromo-analogue, was synthesized from the 2-amino-5-bromopyridine via a progressive elongation of the skeleton. The four compounds described are all full antagonists and show good in vitro binding affinities (K-i). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00287-x

文献信息

• N-Oxide analogs of WAY-100635: new high affinity 5-HT1A receptor antagonists
  作者：Sandrine Marchais-Oberwinkler、Bartek Nowicki、Victor W. Pike、Christer Halldin、Johan Sandell、Yuan-Hwa Chou、Balazs Gulyas、Lise T. Brennum、Lars Farde、Håkan V. Wikström

  DOI：10.1016/j.bmc.2004.10.033

  日期：2005.2

  WAY-100635 [N-(2-(1-(4-(2-methoxyphenyl)piperazinyl)ethyl))-N-(2-pyridinyl)cyclohexanecarbox amide] 1 and its O-desmethyl derivative DWAY 2 are well-known high affinity 5-HT(1A) receptor antagonists, which when labeled with carbon-11 (beta+; t(1/2) = 20.4 min) in the carbonyl group are effective radioligands for imaging brain 5-HT(1A) receptors with positron emission tomography (PET). In a search for

  WAY-100635 [N-（2-（1-（4-（2-甲氧基苯基）哌嗪基）乙基））-N-（2-吡啶基）环己烷甲酰胺] 1及其O-去甲基衍生物DWAY 2众所周知亲和力5-HT（1A）受体拮抗剂，当在羰基基团上用碳11（beta +; t（1/2）= 20.4 min）标记时，是对正电子发射的大脑5-HT（1A）受体成像的有效放射性配体断层扫描（PET）。为了寻找具有不同药代动力学和代谢特性的新型5-HT（1A）拮抗剂，将吡啶基N-氧化物部分掺入1和2的类似物中。NOWAY 3，其中1的吡啶基环被氧化为吡啶基N -通过在2-氯吡啶-N-氧化物上进行2- [4-（2-甲氧基苯基）哌嗪-1-基]乙胺的亲核取代，然后用环己烷羰基氯酰化来制备-环氧乙烷。6Cl-NOWAY 4 通过用环己烷羰基处理1-（2-甲氧基苯基）-4-（2-（2-（2-（6-溴）氨基吡啶基-N-氧化物）乙基）哌嗪，制备了更具亲脂