N-(2-(1-(4-(2-methoxyphenyl)piperazinyl)ethyl))-N-(2-(6-bromo)pyridinyl)cyclohexane carboxamide | 345966-41-8

• 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: N-(2-(1-(4-(2-methoxyphenyl)piperazinyl)ethyl))-N-(2-(6-bromo)pyridinyl)cyclohexane carboxamide
• 英文别名: 6BPWAY；N-(6-bromopyridin-2-yl)-N-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]cyclohexanecarboxamide
• CAS: 345966-41-8
• 化学式: C₂₅H₃₃BrN₄O₂
• 分子量: 501.467
• InChiKey: SQMBHDIRXKUQQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  48.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-(1-(4-(2-methoxyphenyl)piperazinyl)ethyl))-N-(2-(6-bromo)pyridinyl)cyclohexane carboxamide 在 钯 六甲基二锡 、 sodium iodide 、 chloroamine-T 作用下， 生成 N-(6-(125I)iodanylpyridin-2-yl)-N-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]cyclohexanecarboxamide
  参考文献：
  名称：

  Synthesis of [phenyl-2-3H]-travoprost: isopropyl ester prodrug of a selective prostaglandin FP receptor agonist

  摘要：

  描述了一种新型降眼压前列腺素氚标记曲伏前列素的制备方法。已鉴定出一种高度选择性的催化脱碘反应，可通过单一合成步骤从 2'-碘-曲伏前列素提供[苯基-2-3H]-曲伏前列素。版权所有 © 2001 约翰·威利父子有限公司

  DOI：

  10.1002/jlcr.441
• 作为产物：
  描述：

  2,6-二溴吡啶氧化物 在 铁粉 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 正丁醇 为溶剂， 反应 54.0h， 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

文献信息

• Synthesis of a [6- Pyridinyl - 18 F]-labelled fluoro derivative of WAY-100635 as a candidate radioligand for brain 5-HT 1A receptor imaging with PET
  作者：Mylène Karramkam、Françoise Hinnen、Myriam Berrehouma、Christophe Hlavacek、Françoise Vaufrey、Christer Halldin、Julie A. McCarron、Victor W. Pike、Frédéric Dollé

  DOI：10.1016/s0968-0896(03)00225-6

  日期：2003.7

  6b-d). Comparative radiolabelling of these precursors with fluorine-18 (positron-emitting isotope, 109.8 min half-life) clearly demonstrated that only ortho-fluorination in this pyridine series, and not meta-fluorination, is of interest for the preparation of a radioligand by nucleophilic heteroaromatic substitution. 6-[(18)F]Fluoro-WAY-100635 ([(18)F]5a) can be efficiently synthesized in one step, either

  近年来，人们在设计，合成和药理表征5-HT（1A）受体拮抗剂WAY-100635的放射性氟化衍生物上进行了大量工作，以利用PET在人脑中体内研究这些受体。合成了WAY-100635的（吡啶基-6）-氟和（吡啶基-5）-氟类似物（6-氟和5-氟WAY-100635，5a / 6a）以及相应的氯，溴-和硝基衍生物作为标记的前体（5b-d和6b-d）。这些前体与氟18的比较放射性标记（发射正电子的同位素，半衰期为109.8分钟）清楚地表明，只有这种吡啶系列中的邻位氟化而不是间位氟化对通过亲核试剂制备放射性配体感兴趣杂芳族取代。6-[（（18F）] Fluoro-WAY-100635（[（18F）] 5a）可以一步有效地从相应的6-溴前体中合成（使用常规方法在145摄氏度下加热10分钟）或来自相应的6-硝基前体（使用100 W微波活化1分钟）。通常，使用15-25 mCi（0.55-0.92 GBq）的6-[（（18）F]
• Sandell, J.; McCarron, J. A.; Halldin, C., Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S167 - S169
  作者：Sandell, J.、McCarron, J. A.、Halldin, C.、Pike, V. W.、Gulyas, B.、Cselenyi, Z.、Sovago, J.、Marchais, S.、Wikstroem, H. V.、Farde, L.

  DOI：——

  日期：——
• Short and efficient syntheses of analogues of way-100635: new and potent 5-HT1A receptor antagonists
  作者：Sandrine Marchais、Bartek Nowicki、Håkan Wikström、Lise T. Brennum、Christer Halldin、Victor W. Pike

  DOI：10.1016/s0968-0896(00)00287-x

  日期：2001.3

  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.
• Synthesis of [phenyl-2-3H]-travoprost: isopropyl ester prodrug of a selective prostaglandin FP receptor agonist
  作者：Robert Selliah、Anura Dantanarayana、Karen Haggard、Judith Egan、Ernest U. Do、Jesse A. May

  DOI：10.1002/jlcr.441

  日期：2001.3.15

  A method for the preparation of tritium labeled travoprost, a new ocular hypotensive prostaglandin, is described. A highly selective catalytic deiodination has been identified which provides [phenyl-2-3H]-travoprost in a single synthetic step from 2′-iodo-travoprost. Copyright © 2001 John Wiley & Sons, Ltd.

  描述了一种新型降眼压前列腺素氚标记曲伏前列素的制备方法。已鉴定出一种高度选择性的催化脱碘反应，可通过单一合成步骤从 2'-碘-曲伏前列素提供[苯基-2-3H]-曲伏前列素。版权所有 © 2001 约翰·威利父子有限公司