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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10301 - Atomic, molecular and chemical physics (physics of atoms and molecules including collision, interaction with radiation, magnetic resonances, Mössbauer effect)

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Molecular Liquids

ISSN

0167-7322

e-ISSN

—

Svazek periodika

385

Číslo periodika v rámci svazku

September

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

10

Strana od-do

—

Kód UT WoS článku

001034566100001

EID výsledku v databázi Scopus

2-s2.0-85163831508