An alternative route to the arylvinyltriazole nucleosides

Chudinov, M. V.; Prutkov, Alexander N.; Matveev, A. V.; Grebenkina, Lyubov E.; Konstantinova, Irina D.; Berezovskaya, Yu. V.

doi:10.1016/j.bmcl.2016.05.072

Cited by 13 publications

(6 citation statements)

References 10 publications

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“…Neither of them displayed anti‐influenza A activity (H5 N1). These results confirm that the antiviral activity was influenced by the rigid bond between the triazole ring and aryl moiety, however, the steric molecular parameters contributed more significantly to activity than multiple bonds conjugation …”

Section: Introductionsupporting

confidence: 69%

“…These results confirm that the antiviral activity was influenced by the rigid bond between the triazole ring and aryl moiety, however, the steric molecular parameters contributed more significantly to activity than multiple bonds conjugation. [60] On the same line, Chudinov et al prepared ribavirin analogs, 5-alkyl-substituted 1-β-D-ribofuranosyl-1,2,4-triazole-3carboxamides (41) ( Figure 12) and their antiviral activity was estimated in vitro on the reproduction of hepatitis C, herpes simplex, and influenza A viruses in cell cultures. Ribavirin (RBV) has been used as a positive control.…”

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%

“…For the manifestation of antiviral activity, the presence of a rigid bond in position 3(5) is necessary, since replacing the ethynyl group with a more flexible single bond or simple alkyl substituents leads to a loss of the activity. In addition, antiviral activity depends on the lipophilicity of the substituent in the p‐position of the aromatic ring and geometry …”

Section: Introductionmentioning

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: 69%

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%

Section: Introductionmentioning

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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“…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]. Рис.…”

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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An alternative route to the arylvinyltriazole nucleosides

Cited by 13 publications

References 10 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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