4-[18F]fluoro-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide | 1310058-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[18F]fluoro-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide
• 英文别名: [18F]FITM；4-(18F)fluoranyl-N-methyl-N-[4-[6-(propan-2-ylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]benzamide
• CAS: 1310058-65-1
• 化学式: C₁₈H₁₈FN₅OS
• 分子量: 370.44
• InChiKey: WIVGIKIKQHUFOD-AWDFDDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-nitro-N-[4-(6-(isopropylamino)pyrimidin-4-yl)-1,3-thiazol-2-yl]-N-methylbenzamide 在 potassium [¹⁸F]fluoride 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 生成 4-[18F]fluoro-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide
  参考文献：
  名称：

  Radiosynthesis and preliminary evaluation of 4-[18F]fluoro-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide as a new positron emission tomography ligand for metabotropic glutamate receptor subtype 1

  摘要：

  The purpose of this study was to develop 4-[F-18]fluoro-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide ([F-18]FITM, [F-18]4) as a new PET ligand for imaging metabotropic glutamate receptor subtype 1 (mGluR1). [F-18]4 was synthesized by [F-18]fluorination of a novel nitro precursor 3 with [F-18]KF in the presence of Kryptofix 222. At the end of synthesis, 429-936 MBq (n = 8) of [F-18]4 was obtained with > 99% radiochemical purity and 204-559 GBq/mu mol specific activity starting from 6.7 to 13.0 GBq of [F-18]F. The brain distribution of [F-18]4 was determined by the in vitro and ex vivo autoradiography using rat brain sections. The in vitro and in vivo specific binding of [F-18]4 to mGluR1 was detected in the cerebellum, thalamus, hippocampus, and striatum. These results suggest that [F-18]4 is a promising PET ligand for the in vivo evaluation of mGluR1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.046

文献信息

• A concise method for fully automated radiosyntheses of [¹⁸F]JNJ-46356479 and [¹⁸F]FITM <i>via</i> Cu-mediated ¹⁸F-fluorination of organoboranes
  作者：Gengyang Yuan、Timothy M. Shoup、Sung-Hyun Moon、Anna-Liisa Brownell

  DOI：10.1039/d0ra04943c

  日期：——

  A modified alcohol-enhanced ¹⁸F-fluorodeboronation has been developed for the radiosyntheses of [¹⁸F]JNJ-46356479 and [¹⁸F]FITM.

  已开发出一种改进的醇增强¹⁸F-氟去硼化法，用于合成[¹⁸F]JNJ-46356479和[¹⁸F]FITM的放射性同位素。
• Radiosynthesis and preliminary evaluation of 4-[18F]fluoro-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide as a new positron emission tomography ligand for metabotropic glutamate receptor subtype 1
  作者：Tomoteru Yamasaki、Masayuki Fujinaga、Yuichiro Yoshida、Katsushi Kumata、Joji Yui、Kazunori Kawamura、Akiko Hatori、Toshimitsu Fukumura、Ming-Rong Zhang

  DOI：10.1016/j.bmcl.2011.03.046

  日期：2011.5

  The purpose of this study was to develop 4-[F-18]fluoro-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide ([F-18]FITM, [F-18]4) as a new PET ligand for imaging metabotropic glutamate receptor subtype 1 (mGluR1). [F-18]4 was synthesized by [F-18]fluorination of a novel nitro precursor 3 with [F-18]KF in the presence of Kryptofix 222. At the end of synthesis, 429-936 MBq (n = 8) of [F-18]4 was obtained with > 99% radiochemical purity and 204-559 GBq/mu mol specific activity starting from 6.7 to 13.0 GBq of [F-18]F. The brain distribution of [F-18]4 was determined by the in vitro and ex vivo autoradiography using rat brain sections. The in vitro and in vivo specific binding of [F-18]4 to mGluR1 was detected in the cerebellum, thalamus, hippocampus, and striatum. These results suggest that [F-18]4 is a promising PET ligand for the in vivo evaluation of mGluR1. (C) 2011 Elsevier Ltd. All rights reserved.