Literature DB >> 19691349

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

Lak Shin Jeong1, 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.   

Abstract

The first synthesis of 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl pyrimidines as potent anticancer agents was accomplished using the DAST fluorination as a key step. It was first revealed that selenium atom participated in the DAST fluorination of 4'-selenonucleosides and that conformational bias induced by bulky selenium acted as a decisive factor in the DAST fluorination. Among compounds tested, 2'-F-4'-seleno-ara-C (4a) exhibited highly potent anticancer activity in all cancer cell lines tested and was more potent than ara-C (1).

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Year:  2009        PMID： 19691349     DOI： 10.1021/jm900852b

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  5 in total

1.  Novel interactions of fluorinated nucleotide derivatives targeting orotidine 5'-monophosphate decarboxylase.

Authors:  Melissa Lewis; Maria Elena Meza-Avina; Lianhu Wei; Ian E Crandall; Angelica Mara Bello; Ewa Poduch; Yan Liu; Christopher J Paige; Kevin C Kain; Emil F Pai; Lakshmi P Kotra
Journal:  J Med Chem       Date:  2011-03-21       Impact factor: 7.446

2.  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.

Authors:  Nashaat Turkman; Vincenzo Paolillo; Juri G Gelovani; Mian M Alauddin
Journal:  Tetrahedron       Date:  2012-12-16       Impact factor: 2.457

3.  Synthesis, evaluation of anti-HIV-1 and anti-HCV activity of novel 2',3'-dideoxy-2',2'-difluoro-4'-azanucleosides.

Authors:  Saúl Martínez-Montero; Susana Fernández; Yogesh S Sanghvi; Emmanuel A Theodorakis; Mervi A Detorio; Tamara R McBrayer; Tony Whitaker; Raymond F Schinazi; Vicente Gotor; Miguel Ferrero
Journal:  Bioorg Med Chem       Date:  2012-09-23       Impact factor: 3.641

Review 4.  Recent Advances in the Chemical Synthesis and Evaluation of Anticancer Nucleoside Analogues.

Authors:  Mieke Guinan; Caecilie Benckendorff; Mark Smith; Gavin J Miller
Journal:  Molecules       Date:  2020-04-28       Impact factor: 4.411

5.  Synthesis and biological activity of 6-selenocaffeine: potential modulator of chemotherapeutic drugs in breast cancer cells.

Authors:  Inês L Martins; Joana P Miranda; Nuno G Oliveira; Ana S Fernandes; Sandrina Gonçalves; Alexandra M M Antunes
Journal:  Molecules       Date:  2013-05-08       Impact factor: 4.411
  5 in total

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