Thienyl-Based Amides of M2 and Neuraminidase Inhibitors: Synthesis, Structural Characterization, and In Vitro Antiviral Activity Against Influenza a Viruses
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F25%3A10504286" target="_blank" >RIV/00216208:11310/25:10504286 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=C9daRUeyoK" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=C9daRUeyoK</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3390/cryst15090772" target="_blank" >10.3390/cryst15090772</a>
Alternative languages
Result language
angličtina
Original language name
Thienyl-Based Amides of M2 and Neuraminidase Inhibitors: Synthesis, Structural Characterization, and In Vitro Antiviral Activity Against Influenza a Viruses
Original language description
Influenza A viruses that cause pandemics, as well as other harmful pathogens (e.g., SARS-CoV-2 variants), are known as the 'silent bioterrorists' of the 21st century. Due to high mutability, anti-influenza chemotherapeutic treatment is a vital defense strategy to combat both seasonal and pandemic influenza strains, especially when vaccines fail. Consequently, the development of novel therapies to combat this serious threat is of great concern. Hence, in this study, 3-(2-thienyl) acrylic acid (TA) was converted into amides of anti-influenza drugs (aminoadamantanes and oseltamivir) through TBTU-mediated coupling. The crystal structures of the thienyl-based amide hybrids (TA-Am (1), TA-Rim (2), TA-Os-OEt (3), and TA-OsC (4)) were also investigated using single-crystal X-ray diffraction, powder X-ray diffraction (PXRD), and differential scanning calorimetry (DSC). Moreover, the antiviral activities of the hybrids against influenza virus A/Fort Monmouth/1/1947 (H1N1), clinically isolated influenza strain A/Wuhan/359/1995 (H3N2), and oseltamivir-resistant A/Jinnan/15/2009 (H1N1) were evaluated in vitro. Amongst the tested thienyl-based amides, bisamide 8 (Boc-Os-Hda-TA) exhibited the most potent activity against influenza virus A (A/Wuhan/359/1995) with an IC50 value of 18.52 mu g/mL and a selectivity index (SI) = 13.0.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Crystals
ISSN
2073-4352
e-ISSN
2073-4352
Volume of the periodical
15
Issue of the periodical within the volume
9
Country of publishing house
CH - SWITZERLAND
Number of pages
19
Pages from-to
772
UT code for WoS article
001579559600001
EID of the result in the Scopus database
2-s2.0-105017234793