Literature DB >> 31062010

Ring opening of epoxides with [18F]FeF species to produce [18F]fluorohydrin PET imaging agents.

Stefan Verhoog1, Allen F Brooks, Wade P Winton, Benjamin L Viglianti, Melanie S Sanford, Peter J H Scott.   

Abstract

A simple technique for the preparation of [18F]HF has been developed and applied to the generation of an [18F]FeF species for opening sterically hindered epoxides. This method has been successfully employed to prepare four drug-like molecules, including 5-[18F]fluoro-6-hydroxy-cholesterol, a potential adrenal/endocrine PET imaging agent. This easily automated one-pot procedure produces sterically hindered fluorohydrin PET imaging agents in good yields and high molar activities.

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Year:  2019        PMID: 31062010      PMCID: PMC6542722          DOI: 10.1039/c9cc02779c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  28 in total

1.  A new and superior adrenal scanning agent, NP-59.

Authors:  S D Sarkar; H Beierwaltes; R D Ice; G P Basmadjian; K R Hetzel; W P Kennedy; M M Mason
Journal:  J Nucl Med       Date:  1975-11       Impact factor: 10.057

Review 2.  Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography.

Authors:  Philip W Miller; Nicholas J Long; Ramon Vilar; Antony D Gee
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  High-pressure, compact, modular radiosynthesizer for production of positron emitting biomarkers.

Authors:  Bernard Amaraesekera; Phillip D Marchis; Krzysztof P Bobinski; Caius G Radu; Johannes Czernin; Jorge R Barrio; R Michael van Dam
Journal:  Appl Radiat Isot       Date:  2013-04-25       Impact factor: 1.513

4.  Optimization of the preparation of fluorine-18-labeled steroid receptor ligands 16alpha-[18F]fluoroestradiol (FES), [18F]fluoro furanyl norprogesterone (FFNP), and 16beta-[18F]fluoro-5alpha-dihydrotestosterone (FDHT) as radiopharmaceuticals.

Authors:  Dong Zhou; Mai Lin; Norio Yasui; Mohammed H Al-Qahtani; Carmen S Dence; Sally Schwarz; John A Katzenellenbogen
Journal:  J Labelled Comp Radiopharm       Date:  2014-02-17       Impact factor: 1.921

5.  Homogeneous nucleophilic radiofluorination and fluorination with phosphazene hydrofluorides.

Authors:  Bente Mathiessen; Andreas T I Jensen; Fedor Zhuravlev
Journal:  Chemistry       Date:  2011-05-30       Impact factor: 5.236

6.  Alternative synthesis for the preparation of 16α-[(18) F]fluoroestradiol.

Authors:  Hee Seup Kil; Han Yang Cho; Sang Ju Lee; Seung Jun Oh; Dae Yoon Chi
Journal:  J Labelled Comp Radiopharm       Date:  2013-07-09       Impact factor: 1.921

7.  Fluorinated isatin derivatives. Part 2. New N-substituted 5-pyrrolidinylsulfonyl isatins as potential tools for molecular imaging of caspases in apoptosis.

Authors:  Anil K Podichetty; Stefan Wagner; Sandra Schröer; Andreas Faust; Michael Schäfers; Otmar Schober; Klaus Kopka; Günter Haufe
Journal:  J Med Chem       Date:  2009-06-11       Impact factor: 7.446

Review 8.  Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors:  Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal:  Chem Rev       Date:  2013-12-03       Impact factor: 60.622

9.  Stable dialkyl ether/poly(hydrogen fluoride) complexes: dimethyl ether/poly(hydrogen fluoride), a new, convenient, and effective fluorinating agent.

Authors:  Imre Bucsi; Béla Török; Alfonso Iza Marco; Golam Rasul; G K Surya Prakash; George A Olah
Journal:  J Am Chem Soc       Date:  2002-07-03       Impact factor: 15.419

10.  Enantioselective radiosynthesis of positron emission tomography (PET) tracers containing [¹⁸F]fluorohydrins.

Authors:  Thomas J A Graham; R Frederick Lambert; Karl Ploessl; Hank F Kung; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2014-03-31       Impact factor: 15.419

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  5 in total

1.  Synthesis of [18F]-γ-fluoro-α,β,-unsaturated esters and ketones via vinylogous 18F-fluorination of α-diazoacetates with [18F]AgF.

Authors:  Stephen Thompson; So Jeong Lee; Isaac M Jackson; Naoko Ichiishi; Allen F Brooks; Melanie S Sanford; Peter J H Scott
Journal:  Synthesis (Stuttg)       Date:  2019-12       Impact factor: 3.157

2.  Copper-Mediated Late-stage Radiofluorination: Five Years of Impact on Pre-clinical and Clinical PET Imaging.

Authors:  Jay S Wright; Tanpreet Kaur; Sean Preshlock; Sean S Tanzey; Wade P Winton; Liam S Sharninghausen; Nicholas Wiesner; Allen F Brooks; Melanie S Sanford; Peter J H Scott
Journal:  Clin Transl Imaging       Date:  2020-05-26

3.  Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters.

Authors:  Liyin Jiang; Pau Sarró; Wei Jie Teo; Jordi Llop; Marcos G Suero
Journal:  Chem Sci       Date:  2022-03-15       Impact factor: 9.825

4.  Fluorination of silyl prosthetic groups by fluorine mediated silyl ether linker cleavage: a concept study with conditions applicable in radiofluorination.

Authors:  Carsten Sven Kramer; Luca Greiner; Klaus Kopka; Martin Schäfer
Journal:  EJNMMI Radiopharm Chem       Date:  2022-06-25

Review 5.  Closing the gap between 19F and 18F chemistry.

Authors:  Javier Ajenjo; Gianluca Destro; Bart Cornelissen; Véronique Gouverneur
Journal:  EJNMMI Radiopharm Chem       Date:  2021-09-25
  5 in total

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