Novel 5-alkyl(aryl)-substituted ribavirine analogues: synthesis and antiviral evaluation

Chudinov, M. V.; Matveev, A. V.; Prutkov, Alexander N.; Konstantinova, Irina D.; Fateev, Ilja V.; Prasolov, V. S.; Smirnova, Olga A.; Ivanov, Alexander; Галегов, Г. А.; Deryabin, P. G.

doi:10.1016/j.mencom.2016.04.012

Cited by 17 publications

(11 citation statements)

References 17 publications

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“…Preliminary SARs revealed that t he presence of alkyl substituents at the 5‐position of the heterocyclic base diminished ribavirin analogs′ antiviral activity. Such results indirectly support the hypothesis that the antiviral activity of ribavirin analogs is correlated with the presence of rigid ethynyl group or isosteric fragment at the 5‐position of the 1,2,4‐triazole ring …”

Section: Introductionsupporting

confidence: 74%

“…Such results indirectly support the hypothesis that the antiviral activity of ribavirin analogs is correlated with the presence of rigid ethynyl group or isosteric fragment at the 5-position of the 1,2,4-triazole ring. [61] By notifying the SARs of the most important active compounds that can serve as potential lead compounds, they have common features. 3(5)-Arylethynyltriazole motif is coplanar which could serve as a potential surrogate for large nucleobases such as purines.…”

Section: Ribavirinmentioning

confidence: 99%

“…In addition, antiviral activity depends on the lipophilicity of the substituent in the p-position of the aromatic ring and geometry. [60][61][62]…”

Section: Ribavirinmentioning

confidence: 99%

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Recent Advances in 1,2,4‐Triazole Scaffolds as Antiviral Agents

El‐Sebaey

2020

ChemistrySelect

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In recent years, severe viral infections have emerged, and antiviral chemotherapeutic agents are not adequately effective in curing these infections, leading to serious human diseases and loss of life. Consequently, a novel antiviral is urgently needed, which undoubtedly essential for the therapy of various fatal and debilitating viral infections. 1,2,4-Triazole derivatives occupy a pivotal position in modern medicinal chemistry and have been incorporated in numerous clinical drugs, including antiviral drugs. To my best knowledge, there are few review articles exclusively handling 1,2,4-triazole scaffold with the antiviral potential. This review aims to figure out recent perspectives and advances of 1,2,4-triazole nucleus roles in various kinds of antiviral agents over the past decade, with some examples of rational design and some structure-activity relationships. This review will hopefully provide perception into especially powerful compounds as lead structures and help in the rational design and development of novel 1,2,4-triazolebased compounds with strong anti-virus efficacy.

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Section: Introductionsupporting

confidence: 74%

Section: Ribavirinmentioning

confidence: 99%

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Recent Advances in 1,2,4‐Triazole Scaffolds as Antiviral Agents

El‐Sebaey

2020

ChemistrySelect

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“…Выяснилось, что противовирусную активность проявляют не только нуклеозиды или ациклические нуклеозидные аналоги, но и их защищенные производные, и сами гетероциклические основания, у которых активность оказалась максимальна. Предположить в этом случае механизм, включающий синтез нуклеозида из основания с участием PNP, невозможно, так как столь объемный заместитель в 5-ом положении ограничивает субстратную специфичность фермента [97,105]. Остается полагать, что за противовирусную активность отвечает само гетероциклическое основание, а гликозидный фрагмент несет скорее транспортную функцию.…”

Section: аналоги рибавирина замещенные по 5-му положению гетероциклаunclassified

“…Ведь одно из наиболее активных соединений -не нуклеозид, а защищенное производное 25, неспособное участвовать в соответствующих метаболических каскадах, к тому же это единственное из активных производных, вообще не содержащее арильного кольца. Нуклеозидные аналоги с простыми алкильными заместителями в положении 5 триазольного цикла практически неактивны против вируса гепатита С на клеточных моделях in vitro [105], а содержащие двойную связь аналоги соединения 26 (рис. 11) активны при транс-конфигурации (EC 50 = 9 мкМ, СС 50 > 30 мкМ) и неактивны в случае цис-конфигурации [109].…”

Section: аналоги рибавирина замещенные по 5-му положению гетероциклаunclassified

Ribavirin and its analogs: Сan you teach an old dog new tricks?

Chudinov

2019

Fine Chem. Tech.

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The review article focuses on the current state of synthetic and biological studies of ribavirin analogs. Ribavirin is a broad-spectrum nucleoside antiviral drug with a 50-year long history of research and application, but its mechanism of action still remains unclear. This article examines contemporary views on the antiviral and antitumor effects of ribavirin and its analogs and describes the contradictions and gaps that exist in our knowledge. In recent years, new nucleoside analogs of ribavirin have been synthesized. These ribavirin derivatives modified at the heterocyclic base, have the potential to become the antiviral and antitumor agents of the new generation. Thus, this paper presents a systematic review of antiviral activities, antitumor activities and structure–activity relationship (SAR) correlations of 39 ribavirin analogs created in the past 15 years. Biological targets and possible mechanisms of action of these new compounds are also discussed, as well as the prospects and possible directions for further research.

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Other Carbon–Nitrogen Bond‐Forming Biotransformations

Żądło‐Dobrowolska

Kroutil

2020

Applied Biocatalysis

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Novel 5-alkyl(aryl)-substituted ribavirine analogues: synthesis and antiviral evaluation

Cited by 17 publications

References 17 publications

Recent Advances in 1,2,4‐Triazole Scaffolds as Antiviral Agents

Recent Advances in 1,2,4‐Triazole Scaffolds as Antiviral Agents

Ribavirin and its analogs: Сan you teach an old dog new tricks?

Other Carbon–Nitrogen Bond‐Forming Biotransformations

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