2014
DOI: 10.1002/cmdc.201402465
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Design, Synthesis, and Biological Evaluation of Unconventional Aminopyrimidine, Aminopurine, and Amino‐1,3,5‐triazine Methyloxynucleosides

Abstract: Herein we describe a class of unconventional nucleosides (methyloxynucleosides) that combine unconventional nucleobases such as substituted aminopyrimidines, aminopurines, or aminotriazines with unusual sugars in their structures. The allitollyl or altritollyl derivatives were pursued as ribonucleoside mimics, whereas the tetrahydrofuran analogues were pursued as their dideoxynucleoside analogues. The compounds showed poor, if any, activity against a broad range of RNA and DNA viruses, including human immunode… Show more

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Cited by 9 publications
(3 citation statements)
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“…2-(4-methyl-5-nitro-6-(pyrrolidin-1-yl)-pyrimidin-2-ylamino)-3-phenylpropanoic acid (Fig. 39) exhibited antiviral activity with IC 50 of 73 μg mLG 1 (Danesh et al, 2015) while 2,4diaminopyrimidine derivative (IC 50 = 13 μg mLG 1 ) was the most effective among the series screened by Fernandez-Cureses et al (2015). Other recently reported pyrimidines with promising antiviral activities in Fig.…”
Section: Antiviral Activitymentioning
confidence: 94%
“…2-(4-methyl-5-nitro-6-(pyrrolidin-1-yl)-pyrimidin-2-ylamino)-3-phenylpropanoic acid (Fig. 39) exhibited antiviral activity with IC 50 of 73 μg mLG 1 (Danesh et al, 2015) while 2,4diaminopyrimidine derivative (IC 50 = 13 μg mLG 1 ) was the most effective among the series screened by Fernandez-Cureses et al (2015). Other recently reported pyrimidines with promising antiviral activities in Fig.…”
Section: Antiviral Activitymentioning
confidence: 94%
“…5 Whatever the origin of pyrimidine occurrence, whether natural or synthesized, it has proved to be privileged for therapeutics as remarkable pharmacophores. Some of the fused heterocyclic ring systems are potential antibacterial (5-amino-thiazolo [4,5d]pyrimidine), 6 antifungal (pyrrolo [2,3-d]pyrimidines), 7 anti-viral (2,4-diaminopyrimidinederivative), 8 anticancer (pyrazolopyrimidine), 9 anti-inflammatory and analgesic (N-(4-hydroxy-6-tosyl-5,6,7,8-tetrahydropyrido [4,3-d]pyrimidin-2-yl)isonicotinamide), 10 and antimalarial (sulfadiazine) agents, as shown in Figure 1. These heterocyclic compounds are highly recognized chemical building blocks with significant medicinal applications.…”
Section: Introductionmentioning
confidence: 99%
“…Chloro-substituted triazines are not very reactive and substitution of the chlorine atom by alcohols requires strong reaction conditions (Afonso et al, 2006). The synthesis of PMEO-5-aza-DAPym (19, Scheme 1) was initially attempted following a procedure similar to our described method for the synthesis of amino-1,3,5-triazine methyloxynucleosides (Fernández-Cureses et al, 2015). Treatment of 6-chloro-2,4-diamino-1,3,5-triazine (17) with an excess of phosphonate 18 (Naperville et al, 1999), in the presence of sodium hydride under microwave irradiation at 100 °C (Scheme 1) failed to produce the desired phosphonate 19 and led to a complex reaction mixture that could not be identified.…”
mentioning
confidence: 99%