Literature DB >> 2826784

Effect of acyclic pyrimidines related to 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine on herpesviruses.

L M Beauchamp1, B L Serling, J E Kelsey, K K Biron, P Collins, J Selway, J C Lin, H J Schaeffer.   

Abstract

A series of pyrimidines related to the potent antiherpetic agent 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine (1, BW B759U), all containing the same acyclic chain, have been synthesized. Some of the compounds were derivatives of the naturally occurring bases, cytosine, uracil, and thymine; others included compounds in which the 5-position of the cytosine and uracil moieties were substituted by bromo, iodo, fluoro, methyl, and amino groups. Other variations of the cytosine derivatives were the 5-aza, 2-mercapto, 4-methylamino, 4-dimethylamino, and isocytosine congeners. A 4-aminopyrimidine adduct was also made. Antiviral testing showed that 1-[(1,3-dihydroxy-2-propoxy)methyl]cytosine (18, BW A1117U) was equivalent to the guanine analogue in potency against human cytomegalovirus and Epstein Barr virus. Other compounds in the series were largely inactive in antiviral screening against the herpesviruses.

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Year:  1988        PMID: 2826784     DOI: 10.1021/jm00396a021

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


  6 in total

1.  Inhibitory effects of acyclic nucleoside phosphonate analogs, including (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine, on Epstein-Barr virus replication.

Authors:  J C Lin; E De Clercq; J S Pagano
Journal:  Antimicrob Agents Chemother       Date:  1991-11       Impact factor: 5.191

2.  Comparison of two bromovinyl nucleoside analogs, 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil and E-5-(2-bromovinyl)-2'-deoxyuridine, with acyclovir in inhibition of Epstein-Barr virus replication.

Authors:  J C Lin; H Machida
Journal:  Antimicrob Agents Chemother       Date:  1988-07       Impact factor: 5.191

3.  A point mutation in the human cytomegalovirus DNA polymerase gene confers resistance to ganciclovir and phosphonylmethoxyalkyl derivatives.

Authors:  V Sullivan; K K Biron; C Talarico; S C Stanat; M Davis; L M Pozzi; D M Coen
Journal:  Antimicrob Agents Chemother       Date:  1993-01       Impact factor: 5.191

4.  Some biochemical properties of an acyclic oligonucleotide analogue. A plausible ancestor of the DNA?

Authors:  L Merle; G Spach; Y Merle; J Sági; A Szemzö
Journal:  Orig Life Evol Biosph       Date:  1993-04       Impact factor: 1.950

5.  Acyclonucleosides: Part 2. diseco-Nucleosides.

Authors:  E S H El Ashry; Y El Kilany
Journal:  Adv Heterocycl Chem       Date:  2008-02-28       Impact factor: 3.552

6.  Novel Nucleoside Analogues as Effective Antiviral Agents for Zika Virus Infections.

Authors:  Marcella Bassetto; Cecilia M Cima; Mattia Basso; Martina Salerno; Frank Schwarze; Daniela Friese; Joachim J Bugert; Andrea Brancale
Journal:  Molecules       Date:  2020-10-20       Impact factor: 4.411

  6 in total

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