2-(4-{4-[2-(2-fluoroethoxy)phenyl]piperazin-1-yl}butyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione | 1351409-39-6

• 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: 2-(4-{4-[2-(2-fluoroethoxy)phenyl]piperazin-1-yl}butyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione
• 英文别名: O-fluoroethyl-CUMI-101；FECUMI-101；2-(4-(4-(2-(2-fluoroethoxy)phenyl)piperazin-1-yl)butyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione；2-[4-[4-[2-(2-fluoroethoxy)phenyl]piperazin-1-yl]butyl]-4-methyl-1,2,4-triazine-3,5-dione
• CAS: 1351409-39-6
• 化学式: C₂₀H₂₈FN₅O₃
• 分子量: 405.472
• InChiKey: SXCVVYUSUGUSMW-UHFFFAOYSA-N

物化性质

• 沸点：
  540.2±60.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(4-chlorobutyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione 在 caesium carbonate 、 三乙胺 作用下， 以 乙腈 、 正丁醇 为溶剂， 反应 17.0h， 生成 2-(4-{4-[2-(2-fluoroethoxy)phenyl]piperazin-1-yl}butyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione
  参考文献：
  名称：

  [EN] RADIOLABELED COMPOUNDS AND METHODS THEREOF
  [FR] COMPOSÉS RADIOMARQUÉS ET LEURS PROCÉDÉS

  摘要：

  本发明涉及放射诊断化合物，制备这些化合物的方法，以及将其用作HA血清素5-HT1A受体的成像剂，用于PET或SPECT，更好地使用PET的方法。还披露了包含放射标记化合物的成像有效量的组合物。本发明还涉及非放射标记化合物，制备这些化合物的方法，以及将其用于治疗各种神经学和/或精神疾病的方法。

  公开号：

  WO2011150183A1

文献信息

• [EN] RADIOLABELED COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS RADIOMARQUÉS ET LEURS UTILISATIONS
  申请人：UNIV COLUMBIA

  公开号：WO2011140360A1

  公开（公告）日：2011-11-10

  The present invention relates to Radiolabeled Compounds labeled with fluorine, bromine, iodine, carbon, or tritium isotopes and methods of use thereof for treating or preventing a psychiatric disorder in a subject, for stabilizing the mood of a subject having a mood disorder, or as imaging agents for a serotonin receptor. Compositions comprising an imaging-effective amount of a Radiolabeled Compound are also disclosed.

  本发明涉及用氟、溴、碘、碳或氚同位素标记的放射性化合物，以及利用这些化合物治疗或预防受试者的精神障碍，稳定情绪障碍受试者的情绪，或作为血清素受体的成像剂的方法。还公开了包含成像有效量放射性标记化合物的组合物。
• RADIOLABELED COMPOUNDS AND METHODS THEREOF
  申请人：Newington Ian Martin

  公开号：US20130064770A1

  公开（公告）日：2013-03-14

  The present invention relates to radiodiagnostic compounds, methods of making those compounds, and methods of use thereof as imaging agents for preferably a HA serotonin 5-HT1A receptor for use in PET or SPECT, preferably PET. Compositions comprising an imaging-effective amount of radiolabeled compounds are also disclosed. The present invention also relates to non-radiolabeled compounds, methods of making those compounds, and methods of use thereof to treat various neurological and/or psychiatric disorders.

  本发明涉及放射性诊断化合物、制备这些化合物的方法以及将其用作成像剂的方法，优选地用于PET或SPECT，特别是HA 5-HT1A受体，其中包括成像有效量的放射性标记化合物的组合物。本发明还涉及非放射性标记化合物、制备这些化合物的方法以及将其用于治疗各种神经和/或精神障碍的方法。
• Synthesis and evaluation of arylpiperazines derivatives of 3,5-dioxo-(2 H ,4 H )-1,2,4-triazine as 5-HT 1A R ligands
  作者：J.S. Dileep Kumar、Vattoly J. Majo、Jaya Prabhakaran、J. John Mann

  DOI：10.1016/j.bmcl.2014.07.048

  日期：2014.10

  5-HT1AR agonist or partial agonists are established drug candidates for psychiatric and neurological disorders. We have reported the synthesis and evaluation of a series of high affinity 5-HT1AR partial agonist PET imaging agents with greater selectivity over α-1AR. The characteristic of these molecules are 3,5-dioxo-(2H,4H)-1,2,4-triazine skeleton tethered to an arylpiperazine unit through an alkyl side chain. The most potent 5-HT1AR agonistic properties were found to be associated with the molecules bearing C-4 alkyl group as the linker. Therefore development of 3,5-dioxo-(2H,4H)-1,2,4-triazine bearing arylpiperazine derivatives may provide high affinity selective 5-HT1AR ligands. Herein we describe the synthesis and evaluation of the binding properties of a series of arylpiperazine analogues of 3,5-dioxo-(2H,4H)-1,2,4-triazine.
• Synthesis and in vivo evaluation of [18F]2-(4-(4-(2-(2-fluoroethoxy)phenyl)piperazin-1-yl)butyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione ([18F]FECUMI-101) as an imaging probe for 5-HT1A receptor agonist in nonhuman primates
  作者：Vattoly J. Majo、Matthew S. Milak、Jaya Prabhakaran、Pratap Mali、Lyudmila Savenkova、Norman R. Simpson、J. John Mann、Ramin V. Parsey、J. S. Dileep Kumar

  DOI：10.1016/j.bmc.2013.05.050

  日期：2013.9

  The 5-HT1AR partial agonist PET radiotracer, [C-11]CUMI-101, has advantages over an antagonist radiotracer as it binds preferentially to the high affinity state of the receptor and thereby provides more functionally meaningful information. The major drawback of C-11 tracers is the lack of cyclotron facility in many health care centers thereby limiting widespread clinical or research use. We identified the fluoroethyl derivative, 2-(4-(4-(2-(2-fluoroethoxy)phenyl)piperazin-l-yl)buty1)-4-methyl-1,2,4-triazine3,5(2H,4H)dione (FECUMI-101) (K-i = 0.1 nM; E-max = 77%; EC50 = 0.65 nM) as a partial agonist 5-HT1AR ligand of the parent ligand CUM1-101. FECUMI-101 is radiolabeled with F-18 by O-fluoroethylation of the corresponding desmethyl analogue (1) with [F-18]fluoroethyltosylate in DMSO in the presence of 1.6 equiv of K2CO3 in 45 +/- 5% yield (EOS). PET shows [F-18]FECUMI-101 binds specifically to 5-HT1AR enriched brain regions of baboon. The specificity of [F-18]FECUMI-101 binding to 5-HT1AR was confirmed by challenge studies with the known 5-HT1AR ligand WAY100635. These findings indicate that [F-18]FECUM1-101 can be a viable agonist ligand for the in vivo quantification of high affinity 5-HT1AR with PET. (C) 2013 Elsevier Ltd. All rights reserved.
• RADIOLABELED COMPOUNDS AND USES THEREOF
  申请人：MANN Joseph John

  公开号：US20130156699A1

  公开（公告）日：2013-06-20

  The present invention relates to Radiolabeled Compounds labeled with fluorine, bromine, iodine, carbon, or tritium isotopes and methods of use thereof for treating or preventing a psychiatric disorder in a subject, for stabilizing the mood of a subject having a mood disorder, or as imaging agents for a serotonin receptor. Compositions comprising an imaging-effective amount of a Radiolabeled Compound are also disclosed.