Synthesis and anti-viral activity of azolo-adamantanes against influenza A virus

Zarubaev, Vladimir V.; Golod, E. L.; Anfimov, Pavel; Штро, Анна А.; Saraev, V. V.; Gavrilov, A. S.; Logvinov, A. V.; Киселев, О. И.

doi:10.1016/j.bmc.2009.11.047

Cited by 88 publications

(30 citation statements)

References 43 publications

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“…Although Amt and rimantadine are well known antiviral drugs and their structure-activity relationships have been previously examined, 8,31–50 quite surprisingly few ring-contracted or ring-expanded analogs have been synthesized. 32 Moreover, little effort has been paid to investigate the influence of polycyclic scaffolds on the inhibitory activity, 33,51–56 the guanidine 1 and related spiro-piperidine compounds being a notable exception (Chart 1).…”

Section: Chemistrymentioning

confidence: 99%

Exploring the Size Limit of Templates for Inhibitors of the M2 Ion Channel of Influenza A Virus

Duque

Torres

et al. 2011

J. Med. Chem.

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Amantadine inhibits the M2 proton channel of influenza A virus, yet its clinical use has been limited by the rapid emergence of amantadine-resistant virus strains. We have synthesized and characterized a series of polycyclic compounds designed as ring-contracted or ring-expanded analogs of amantadine. Inhibition of the wild-type (wt) M2 channel and the A/M2-S31N and A/M2-V27A mutant ion channels were measured in Xenopus oocytes using two-electrode voltage clamp (TEV) assays. Several bisnoradamantane and noradamantane derivatives inhibited the wt ion channel. The compounds bind to a primary site delineated by Val27, Ala30 and Ser31, though ring-expansion restricts the positioning in the binding site. Only the smallest analog 8 was found to inhibit the S31N mutant ion channel. The structure-activity relationship obtained by TEV assay was confirmed by plaque reduction assays with A/H3N2 influenza virus carrying wt M2 protein.

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Section: Chemistrymentioning

confidence: 99%

Exploring the Size Limit of Templates for Inhibitors of the M2 Ion Channel of Influenza A Virus

Duque

Torres

et al. 2011

J. Med. Chem.

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“…Researches found that the substituent R 1 of compound 168 could affect the yields to some extent. The -NH 2 group was favorable for the transformation with yield up to 67% [241]. This reaction provides a practical synthetic route for the preparation of triazole adamantanes with large steric hindrance to overcome the serious amantadine/rimantadine resistance of influenza viruses.…”

Section: N-alkylation With Alcoholsmentioning

confidence: 93%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

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Heterocyclic 1,2,4-triazole derivatives possess unusually spacious potentiality as medicinal agents, agricultural chemicals, functional materials, ionic liquids, supramolecular catalysts as well as artificial enzymes and receptors for supramolecular recognition and biomimetic catalysis, and their various researches and developments have been being a quite rapidly developing and active highlight topic with an infinite space. Numerous efforts have been directed toward various types of possible applications of 1,2,4-triazole-based compounds and a lot of important progress has been made, especially their preparations have attracted increasing attention. This review systematically summarized the recent advances in the syntheses of 1,2,4-triazole derivatives, including: (1) Cyclizations to form triazole ring; (2) Transformations of heterocyclic compounds to construct triazole ring; (3) Substitutions on 1,2,4-triazole ring; (4) Structural modifications in side chains of 1,2,4-triazole ring. It was hoped that this review would be helpful for the design and development of highly efficient preparation of 1,2,4-triazole derivatives with various sorts and varieties of extensively potential applications in medicine, agriculture, chemistry, materials, supramolecular sciences and so on.

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“…Derivatives of adamantane with nitrogen-containing groups are known to demonstrate antiviral activity, rimantadine being the most well studied among them [1][2][3][4]. Other types of biological activities of adamantane derivatives have also been reported [5][6][7].…”

Section: Introductionmentioning

confidence: 98%

1,3-Bis(1,2,4-triazol-1-yl)adamantane

Marchenko

Potapov

2017

Molbank

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Functional adamantane derivatives are interesting as active pharmaceutical ingredients, building blocks for supramolecular ensembles, and ligands in light of the coordination chemistry of functional materials. In this communication, synthesis of two isomeric 1,3-bis(1,2,4-triazolyl)adamantanes by the reaction of 1,3-dibromoadamantane with 1,2,4-triazole in the absence of solvent is reported. The products, namely 1,3-bis(1,2,4-triazol-1-yl)adamantane and 1-(1,2,4-triazol-1-yl)-3-(1,2,4-triazol-4-yl)adamantane were separated by column chromatography and identified by NMR and mass-spectrometry.

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Synthesis and anti-viral activity of azolo-adamantanes against influenza A virus

Cited by 88 publications

References 43 publications

Exploring the Size Limit of Templates for Inhibitors of the M2 Ion Channel of Influenza A Virus

Exploring the Size Limit of Templates for Inhibitors of the M2 Ion Channel of Influenza A Virus

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

1,3-Bis(1,2,4-triazol-1-yl)adamantane

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