Antiviral docking analysis, semisynthesis and mechanistic studies on the origin of stereo- and chemoselectivity in epoxidation reaction of a‘ -trans-Himachalene

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F46747885%3A24620%2F23%3A00012258" target="_blank" >RIV/46747885:24620/23:00012258 - isvavai.cz</a>
Result on the web
<a href="https://www.sciencedirect.com/science/article/pii/S0167732223010073" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0167732223010073</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.molliq.2023.122204" target="_blank" >10.1016/j.molliq.2023.122204</a>

Result language
angličtina
Original language name
Antiviral docking analysis, semisynthesis and mechanistic studies on the origin of stereo- and chemoselectivity in epoxidation reaction of a‘ -trans-Himachalene
Original language description
Epoxides are of great commercial relevance in several businesses due to their unique attributes. The epoxide C15H22O was synthesized via epoxidizing the α‘-trans-himachalene 4 deploying meta-chloroperbenzoic acid (m-CPBA) in dichloromethane. The chemoselectivity of the reaction was investigated both experimentally and theoretically in the framework of the molecular electron density theory (MEDT). An experimental chemoselectivity with the best C3 = C4 interaction was appropriately determined as predicted by the Parr functions, ELF analysis of the reactants and energetic study. In addition, the epoxidation reaction of α‘-trans-himachalene 4 by m-CPBA possessed a lower activation energy in water and ethanol, which shows that this reaction can be performed in environmentally friendly solvents. The investigation of the mechanism indicates that this epoxidation reaction follows a one-step mechanism. Furthermore, a docking study has been carried out for α‘-trans-himachalene 4, epoxide 5 and epoxide 6 docked in SARS-CoV2 main protease (6LU7) as compared to the Ribavirin, thus indicating that epoxide 6 could be the antiviral drug.
Czech name
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Czech description
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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
10301 - Atomic, molecular and chemical physics (physics of atoms and molecules including collision, interaction with radiation, magnetic resonances, Mössbauer effect)

Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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