Literature DB >> 3625714

Improved synthesis and antitumor activity of 1-deazaadenosine.

G Cristalli, P Franchetti, M Grifantini, S Vittori, T Bordoni, C Geroni.   

Abstract

A more convenient synthetic route to 1-deazaadenosine (1) by reduction of the new nucleoside 7-nitro-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine (6) is reported. Compound 6 was obtained by reaction of 7-nitroimidazo-[4,5-b]pyridine with 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose in the presence of stannic chloride followed by treatment with methanolic ammonia. 1-Deazaadenosine (1) showed good activity in vitro as inhibitor of HeLa, KB, P388, and L1210 leukemia cell line growth, with ID50 values ranging from 0.34 microM (KB) to 1.8 microM (P388). The nitro derivative 6 demonstrated moderate activity against the same cell lines.

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Year:  1987        PMID： 3625714     DOI： 10.1021/jm00392a029

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


  6 in total

1.  Structure-Based Screening of Uncharted Chemical Space for Atypical Adenosine Receptor Agonists.

Authors:  David Rodríguez; Saibal Chakraborty; Eugene Warnick; Steven Crane; Zhan-Guo Gao; Robert O'Connor; Kenneth A Jacobson; Jens Carlsson
Journal:  ACS Chem Biol       Date:  2016-08-22       Impact factor: 5.100

2.  Single-atom imino substitutions at A9 and A10 reveal distinct effects on the fold and function of the hairpin ribozyme catalytic core.

Authors:  Robert C Spitale; Rosaria Volpini; Michael V Mungillo; Jolanta Krucinska; Gloria Cristalli; Joseph E Wedekind
Journal:  Biochemistry       Date:  2009-08-25       Impact factor: 3.162

3.  1-Deazaadenosine: synthesis and activity of base-modified hammerhead ribozymes.

Authors:  F Seela; H Debelak; N Usman; A Burgin; L Beigelman
Journal:  Nucleic Acids Res       Date:  1998-02-15       Impact factor: 16.971

4.  Synthesis of a 6-methyl-7-deaza analogue of adenosine that potently inhibits replication of polio and dengue viruses.

Authors:  Runzhi Wu; Eric D Smidansky; Hyung Suk Oh; Ratree Takhampunya; Radhakrishnan Padmanabhan; Craig E Cameron; Blake R Peterson
Journal:  J Med Chem       Date:  2010-10-22       Impact factor: 7.446

5.  Structure and Base Pairing Properties of a Replicable Nonpolar Isostere for Deoxyadenosine.

Authors:  Kevin M Guckian; Juan C Morales; Eric T Kool
Journal:  J Org Chem       Date:  1998       Impact factor: 4.354

6.  Identification of an imino group indispensable for cleavage by a small ribozyme.

Authors:  Robert C Spitale; Rosaria Volpini; Moriah G Heller; Jolanta Krucinska; Gloria Cristalli; Joseph E Wedekind
Journal:  J Am Chem Soc       Date:  2009-05-06       Impact factor: 15.419
  6 in total

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