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Статья
Stereoselective synthesis of novel adamantane derivatives with high potency against rimantadine-resistant influenza A virus strains
2021
A series of (R)- and (S)-isomers of new adamantane-substituted heterocycles (1,3-oxazinan-2-one, piperidine-2,4-dione, piperidine-2-one and piperidine) with potent activity against rimantadine-resistant strains of influenza A virus were synthesized through the transformation of adamantyl-substituted N-Boc-homoallylamines 8 into piperidine-2,4-diones 11 through the cyclic bromourethanes 9 and key intermediate enol esters 10. Biological assays of the prepared compounds were performed on the rimantadine-resistant S31N mutated strains of influenza A-A/California/7/2009(H1N1)pdm09 and modern pandemic strain A/IIV-Orenburg/29-L/2016(H1N1)pdm09. The most potent compounds were both enantiomers of the enol ester 10 displaying IC50 = 7.7 μM with the 2016 Orenburg strain. © The Royal Society of Chemistry.
Цитирование
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Версии
- 1. Version of Record от 2021-04-27
Метаданные
Название журнала
- Organic and Biomolecular Chemistry
Том
- 15
Выпуск
- 15
Страницы
- 3152-3157
Ключевые слова
- Esters; Isomers; Stereochemistry; Stereoselectivity; Adamantane derivatives; Biological assays; Influenza A virus; Pandemic strains; Potent activity; Potent compounds; Resistant strains; Stereoselective synthesis; Viruses; adamantane; antivirus agent; rimantadine; antiviral resistance; chemistry; drug effects; Influenza A virus (H1N1); stereoisomerism; synthesis; Adamantane; Antiviral Agents; Chemistry Techniques, Synthetic; Drug Resistance, Viral; Influenza A Virus, H1N1 Subtype; Rimantadine; Stereoisomerism
Издатель
- Royal Society of Chemistry
Тип документа
- journal article
Тип лицензии Creative Commons
- CC
Правовой статус документа
- Свободная лицензия
Источник
- scopus
