(4-fluoro-m-hydroxyphenethyl)guanidine | 889882-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (4-fluoro-m-hydroxyphenethyl)guanidine
• 英文别名: 4F-MHPG；[11C]-p-fluoro-m-hydroxy-phenethylguanidine；(11)C-para-fluoro-meta-hydroxy-phenethylguanidine；2-[2-(4-fluoro-3-hydroxyphenyl)ethyl]guanidine
• CAS: 889882-04-6
• 化学式: C₉H₁₂FN₃O
• 分子量: 197.212
• InChiKey: DBVYMDMGVRXUPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-benzyloxy-4-fluorobenzyl alcohol 在 盐酸 、 硼烷四氢呋喃络合物 、 氢溴酸 、 三溴化磷 、 三乙胺 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 59.0h， 生成 (4-fluoro-m-hydroxyphenethyl)guanidine
  参考文献：
  名称：

  Synthesis and bioevaluation of [18F]4-fluoro-m-hydroxyphenethylguanidine ([18F]4F-MHPG): A novel radiotracer for quantitative PET studies of cardiac sympathetic innervation

  摘要：

  A new cardiac sympathetic nerve imaging agent, [F-18]4-fluoro-m-hydroxyphenethylguanidine ([F-18]4F-MHPG), was synthesized and evaluated. The radiosynthetic intermediate [F-18]4-fluoro-m-tyramine ([F-18]4F-MTA) was prepared and then sequentially reacted with cyanogen bromide and NH4Br/NH4OH to afford [F-18]4F-MHPG. Initial bioevaluations of [F-18]4F-MHPG (biodistribution studies in rats and kinetic studies in the isolated rat heart) were similar to results previously reported for the carbon-11 labeled analog [C-11]4F-MHPG. The neuronal uptake rate of [F-18]4F-MHPG into the isolated rat heart was 0.68 ml/min/g wet and its retention time in sympathetic neurons was very long (T-1/2 > 13 h). A PET imaging study in a nonhuman primate with [F-18]4F-MHPG provided high quality images of the heart, with heart-to-blood ratios at 80-90 min after injection of 5-to-1. These initial kinetic and imaging studies of [F-18]4F-MHPG suggest that this radiotracer may allow for more accurate quantification of regional cardiac sympathetic nerve density than is currently possible with existing neuronal imaging agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.106

文献信息

• Imaging agents
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US10259781B2

  公开（公告）日：2019-04-16

  Provided herein is technology relating to imaging agents and particularly, but not exclusively, to methods of manufacturing fluorine-18-labeled phenethylguanidines and uses thereof.

  本文提供的是与成像剂有关的技术，特别是（但不限于）制造氟-18 标记的苯乙胍及其用途的方法。
• [EN] PHOSPHAMIDE DERIVATIVE, METHOD FOR MANUFACTURING THE SAME, AND USES THEREOF<br/>[FR] DÉRIVÉ DE PHOSPHAMIDE, SON PROCÉDÉ DE FABRICATION ET SES UTILISATIONS<br/>[ZH] 一种磷酰胺衍生物及制备方法和用途
  申请人：SICHUAN HAISCO PHARMACEUTICAL CO LTD

  公开号：WO2017133517A1

  公开（公告）日：2017-08-10

  公开了一种磷酰胺衍生物及制备方法和用途。特别公开了一种通式(I)所示化合物及其药学上可接受的盐或立体异构体 (I)，其中，G、L、Q、s如说明书中所定义。
• Radiolabeled Phenethylguanidines:  Novel Imaging Agents for Cardiac Sympathetic Neurons and Adrenergic Tumors
  作者：David M. Raffel、Yong-Woon Jung、David L. Gildersleeve、Phillip S. Sherman、James J. Moskwa、Louis J. Tluczek、Wei Chen

  DOI：10.1021/jm061398y

  日期：2007.5.1

  The norepinephrine transporter (NET) substrates [I-123]-m-iodobenzylguanidine (MIBG) and [C-11]-m-hydroxyephedrine (HED) are used as markers of cardiac sympathetic neurons and adrenergic tumors (pheochromocytoma, neuroblastoma). However, their rapid NET transport rates limit their ability to provide accurate measurements of cardiac nerve density. [C-11]Phenethylguanidine ([C-11]1a) and 12 analogues ([C-11]1b-m) were synthesized and evaluated as radiotracers with improved kinetics for quantifying cardiac nerve density. In isolated rat hearts, neuronal uptake rates of [C-11]1a-m ranged from 0.24 to 1.96 mL min(-1) (g wet wt)(-1), and six compounds had extremely long neuronal retention times (clearance T-1/2 > 20 h) due to efficient vesicular storage. Positron emission tomography (PET) studies in nonhuman primates with [C-11]1e, N-[C-11]guanyl-m-octopamine, which has a slow NET transport rate, showed improved myocardial kinetics compared to HED. Compound [C-11]1c, [C-11]-p-hydroxyphenethylguanidine, which has a rapid NET transport rate, avidly accumulated into rat pheochromocytoma xenograft tumors in mice. These encouraging findings demonstrate that radiolabeled phenethylguanidines deserve further investigation as radiotracers of cardiac sympathetic innervation and adrenergic tumors.
• IMAGING AGENTS
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20150246142A1

  公开（公告）日：2015-09-03

  Provided herein is technology relating to imaging agents and particularly, but not exclusively, to methods of manufacturing fluorine-18-labeled phenethylguanidines and uses thereof.
• Compound Targeting Norepinephrine Transporter
  申请人：GUANGZHOU MIPHERE MEDICAL TECHNOLOGY CO., LTD.

  公开号：US20220096667A1

  公开（公告）日：2022-03-31

  A compound according to following formula can be prepared, where R1 is an F or I residue.