TY - JOUR

T1 - Synthesis, Characterization and Computational Analysis of Thiophene-2,5-Diylbis((3-Mesityl-3-Methylcyclobutyl)Methanone)

AU - Koparir, Pelin

AU - Omar, Rebaz anwar

AU - Sarac, Kamuran

AU - Ahmed, Lana omer

AU - Karatepe, Arzu

AU - Taskin-Tok, Tugba

AU - Safin, Damir a.

N1 - This work was supported by state assignment of the Ministry of Science and Higher Education of the Russian Federation [Project Reg. No. 720000Ф.99.1.БЗ85АА13000].

PY - 2023/8/9

Y1 - 2023/8/9

N2 - In this work, we report synthesis, characterization and computational studies of the symmetric thiophene-based compound thiophene-2,5-diylbis((3-mesityl-3-methylcyclobutyl)methanone) (1) obtained from 2,2'-thiobis(1-(3-mesityl-3-methylcyclobutyl)ethan-1-one) and glyoxal using the Hinsberg thiophene ring synthesis approach. The Density Functional Theory (DFT) calculations were performed to probe the structure of 1, as well as its electronic and optical properties. The global reactivity descriptors, as well as molecular electrostatic potential (MEP), were revealed to probe the reactivity and to determine the reactive centers of 1. The DFT calculations were also applied to probe 1 as a potential corrosion inhibitor for some important metals used in implants. Electron charge transfer from the molecule of 1 to the surface of Ni, Au, Co, Cu, Mo, W, Fe and Cr was revealed. Bioavailability, druggability as well as absorption, distribution, metabolism, excretion and toxicity properties of 1 were predicted. Molecular docking was applied to examine the influence of this compound on a series of the SARS-CoV-2 proteins. Compound 1 exhibited the best binding affinity with the Nsp14 (N7-MTase), Papain-like protease (PLpro) and Nsp16 (MGP site) proteins as well as demonstrated a similar efficiency toward both the native and mutated Spike proteins, RDB.

AB - In this work, we report synthesis, characterization and computational studies of the symmetric thiophene-based compound thiophene-2,5-diylbis((3-mesityl-3-methylcyclobutyl)methanone) (1) obtained from 2,2'-thiobis(1-(3-mesityl-3-methylcyclobutyl)ethan-1-one) and glyoxal using the Hinsberg thiophene ring synthesis approach. The Density Functional Theory (DFT) calculations were performed to probe the structure of 1, as well as its electronic and optical properties. The global reactivity descriptors, as well as molecular electrostatic potential (MEP), were revealed to probe the reactivity and to determine the reactive centers of 1. The DFT calculations were also applied to probe 1 as a potential corrosion inhibitor for some important metals used in implants. Electron charge transfer from the molecule of 1 to the surface of Ni, Au, Co, Cu, Mo, W, Fe and Cr was revealed. Bioavailability, druggability as well as absorption, distribution, metabolism, excretion and toxicity properties of 1 were predicted. Molecular docking was applied to examine the influence of this compound on a series of the SARS-CoV-2 proteins. Compound 1 exhibited the best binding affinity with the Nsp14 (N7-MTase), Papain-like protease (PLpro) and Nsp16 (MGP site) proteins as well as demonstrated a similar efficiency toward both the native and mutated Spike proteins, RDB.

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=000843105100001

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85136579915

U2 - 10.1080/10406638.2022.2112712

DO - 10.1080/10406638.2022.2112712

M3 - Article

VL - 43

SP - 6107

EP - 6125

JO - Polycyclic Aromatic Compounds

JF - Polycyclic Aromatic Compounds

SN - 1040-6638

IS - 7

ER -