Literature DB >> 23316091

An investigation on stereospecific fluorination at the 2'-arabino-position of a pyrimidine nucleoside: radiosynthesis of 2'-deoxy-2'-[(18)F]fluoro-5-methyl-1-β-D-arabinofuranosyluracil.

Nashaat Turkman1, Vincenzo Paolillo, Juri G Gelovani, Mian M Alauddin.   

Abstract

Direct fluorination at the 2'-arabino-position of a pyrimidine nucleoside has been a long-standing challenge, yet we recently reported such a stereospecific fluorination for the first time in the synthesis of [(18)F]FMAU, albeit in low yields. Herein we report the results of an investigation on stereospecific fluorination on a variety of precursors for synthesis of [(18)F]FMAU. Several precursors were synthesized in multiple steps and fluorination was performed at the 2'-arabino position using K[(18)F]/kryptofix 2.2.2. All precursors produced [(18)F]FMAU in low yields.

Entities:  

Year:  2012        PMID： 23316091      PMCID： PMC3539786          DOI： 10.1016/j.tet.2012.10.001

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  22 in total

1.  Nucleosides and nucleotides. 95. Improved synthesis of 1-(2-azido-2-deoxy-beta-D-arabinofuranosyl)cytosine (cytarazid) and -thymine. Inhibitory spectrum of cytarazid on the growth of various human tumor cells in vitro.

Authors:  A Matsuda; J Yasuoka; T Sasaki; T Ueda
Journal:  J Med Chem       Date:  1991-03       Impact factor: 7.446

2.  2'-fluoro-5-iodo-aracytosine, a potent and selective anti-herpesvirus agent.

Authors:  C Lopez; K A Watanabe; J J Fox
Journal:  Antimicrob Agents Chemother       Date:  1980-05       Impact factor: 5.191

3.  Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides.

Authors:  K A Watanabe; U Reichman; K Hirota; C Lopez; J J Fox
Journal:  J Med Chem       Date:  1979-01       Impact factor: 7.446

4.  Pyrimidine nucleoside transformations via anhydronucleosides.

Authors:  J J Fox
Journal:  Pure Appl Chem       Date:  1969       Impact factor: 2.453

5.  Synthesis and evaluation of 2'-deoxy-2'-18F-fluoro-5-fluoro-1-beta-D-arabinofuranosyluracil as a potential PET imaging agent for suicide gene expression.

Authors:  Mian M Alauddin; Antranic Shahinian; Ryan Park; Michel Tohme; John D Fissekis; Peter S Conti
Journal:  J Nucl Med       Date:  2004-12       Impact factor: 10.057

6.  Discovery of a new template for anticancer agents: 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl-cytosine (2'-F-4'-seleno-ara-C).

Authors:  Lak Shin Jeong; Dilip K Tosh; Won Jun Choi; Sang Kook Lee; You-Jin Kang; Sun Choi; Jin Hee Lee; Hankil Lee; Hyuk Woo Lee; Hea Ok Kim
Journal:  J Med Chem       Date:  2009-09-10       Impact factor: 7.446

7.  Synthesis of 2'-deoxy-2'-[18F]fluoro-beta-D-arabinofuranosyl nucleosides, [18F]FAU, [18F]FMAU, [18F]FBAU and [18F]FIAU, as potential PET agents for imaging cellular proliferation. Synthesis of [18F]labelled FAU, FMAU, FBAU, FIAU.

Authors:  Thomas J Mangner; Raymond W Klecker; Lawrence Anderson; Anthony F Shields
Journal:  Nucl Med Biol       Date:  2003-04       Impact factor: 2.408

8.  A preclinical model for predicting drug response in soft-tissue sarcoma with targeted AAVP molecular imaging.

Authors:  Amin Hajitou; Dina C Lev; Jonathan A F Hannay; Borys Korchin; Fernanda I Staquicini; Suren Soghomonyan; Mian M Alauddin; Robert S Benjamin; Raphael E Pollock; Juri G Gelovani; Renata Pasqualini; Wadih Arap
Journal:  Proc Natl Acad Sci U S A       Date:  2008-03-12       Impact factor: 11.205

9.  Nucleosides. 129. Synthesis of antiviral nucleosides: 5-alkenyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracils.

Authors:  K A Watanabe; T L Su; U Reichman; N Greenberg; C Lopez; J J Fox
Journal:  J Med Chem       Date:  1984-01       Impact factor: 7.446

10.  Evaluation of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-beta-L: -arabinofuranosyluracil ([18F]-L: -FMAU) as a PET imaging agent for cellular proliferation: comparison with [18F]-D: -FMAU and [18F]FLT.

Authors:  Ryuichi Nishii; Andrei Y Volgin; Osama Mawlawi; Uday Mukhopadhyay; Ashutosh Pal; William Bornmann; Juri G Gelovani; Mian M Alauddin
Journal:  Eur J Nucl Med Mol Imaging       Date:  2007-12-04       Impact factor: 9.236
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.