Crystal structure, DFT studies, Hirshfeld surface and energy framework analysis of 4-(5-nitro-thiophen-2-yl)-pyrrolo [1, 2-a] quinoxaline: A potential SARS-CoV-2 main protease inhibitor

Divya, Kumble; Savitha, D.P.; Krishna, Gopal; Dhanya, T.M.; Mohanan, Pezholil

doi:10.1016/j.molstruc.2021.131932

Cited by 15 publications

(7 citation statements)

References 45 publications

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“…Yadav et al suggested the higher reactivity of favipiravir toward Mpro since the presence of electron donor and receptor groups in favipiravir displayed the capability of forming a complex with the external target molecule. Other similar studies include refs and − . DFT calculations by Aitouna et al , indicated the epoxidation reaction of parthenolide and himachalene derivatives presented high chemoselectivity.…”

Section: Methods and Approachesmentioning

confidence: 83%

Methodology-Centered Review of Molecular Modeling, Simulation, and Prediction of SARS-CoV-2

Gao¹,

Wang²,

Chen³

et al. 2022

Chem. Rev.

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Despite tremendous efforts in the past two years, our understanding of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), virus–host interactions, immune response, virulence, transmission, and evolution is still very limited. This limitation calls for further in-depth investigation. Computational studies have become an indispensable component in combating coronavirus disease 2019 (COVID-19) due to their low cost, their efficiency, and the fact that they are free from safety and ethical constraints. Additionally, the mechanism that governs the global evolution and transmission of SARS-CoV-2 cannot be revealed from individual experiments and was discovered by integrating genotyping of massive viral sequences, biophysical modeling of protein–protein interactions, deep mutational data, deep learning, and advanced mathematics. There exists a tsunami of literature on the molecular modeling, simulations, and predictions of SARS-CoV-2 and related developments of drugs, vaccines, antibodies, and diagnostics. To provide readers with a quick update about this literature, we present a comprehensive and systematic methodology-centered review. Aspects such as molecular biophysics, bioinformatics, cheminformatics, machine learning, and mathematics are discussed. This review will be beneficial to researchers who are looking for ways to contribute to SARS-CoV-2 studies and those who are interested in the status of the field.

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Section: Methods and Approachesmentioning

confidence: 83%

Methodology-Centered Review of Molecular Modeling, Simulation, and Prediction of SARS-CoV-2

Gao¹,

Wang²,

Chen³

et al. 2022

Chem. Rev.

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“…The title compound (5NO 2 TAAPP) (140) was docked into the catalytic binding site of SARS-CoV-2 3CL pro (PDB ID: 6LU7) where it showed binding energy of À 7.95 kcal/mol. [75] Missioui À 6.9 kcal/mol when compared with the standard drug oseltamivir (À 7.0 and À 7.5 kcal/mol). The prediction of in silico ADME and toxicity studies had no carcinogenic effects and no AMES toxicity.…”

Section: Anti-covid-19 Propertymentioning

confidence: 98%

“…Moreover, the intermolecular interaction energies for the title compound were calculated using CE−B3LYP/6‐31 G(d, p) energy model, which revealed that the total energy of the molecule was −154.7 KJ/mol and played a key role in the total forces in the crystal packing. The title compound (5NO 2 TAAPP) ( 140 ) was docked into the catalytic binding site of SARS‐CoV‐2 3CL pro ( PDB ID: 6LU7 ) where it showed binding energy of −7.95 kcal/mol [75] …”

Section: Pharmacological Activities Of Quinoxaline‐based Compoundsmentioning

confidence: 99%

A Review on Multipurpose Potential of Bioactive Heterocycle Quinoxaline

2023

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In last few decades, nitrogen‐containing heterocycles have maintained their status as an important core of FDA‐approved drugs and medicinally active compounds. Quinoxaline is one such class of nitrogen‐containing scaffold that has become a subject of extensive research as it possess a plethora of biological activities. Molecular hybridization is a versatile and rational approach to drug design that involves the combination of two bioactive molecules possessing distinct intrinsic activity into a single scaffold for enhancing their therapeutic potential. In view of this, the advancement and potential of quinoxaline hybrids bearing thiazole, triazole, oxadiazole, pyrrolizines, pyrazole, etc. have attracted the keen attention of researchers to explore their therapeutic ability against different biological targets. The present review includes the research in the recent years (2018–2023) and addresses the graceful advancements in the studies related to quinoxaline‐based small molecules including their synthetic routes, biological activities and structure‐activity relationships. We anticipate that this review article will provide comprehensive knowledge of pharmacological importance of quinoxaline analogues and will fulfill the need of scientific community in designing and developing efficacious novel molecules.

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“…The quinoxaline derivative 4-(5-nitro-thiophen-2-yl)-pyrrolo[1,2- a ]quinoxaline 5NO 2 TAAPP) 76 was prepared by Divya et al, 102 and tested its anti-SARS-CoV-2 main protease 3CL pro (PDB code: 6LU7) activity using molecular docking studies. The compound (5NO 2 TAAPP) 76 showed a lower binding energy towards SARS-CoV-2 main protease 3CL pro (−7.95Kcal mol −1 ) as compared to the reference drugs remdesivir (−4.96Kcal mol −1 ) and hydroxychloroquine (−6.06Kcal mol −1 ).…”

Section: In Silico Studies Of Covid-19mentioning

confidence: 99%

A Comprehensive Update of Anti-COVID-19 Activity of Heterocyclic Compounds

Nazir,

Ahmad,

Aslam

et al. 2024

DDDT

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The Coronavirus disease 2019 (COVID-19) pandemic is one of the most considerable health problems across the world. Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) is the major causative agent of COVID-19. The severe symptoms of this deadly disease include shortness of breath, fever, cough, loss of smell, and a broad spectrum of other health issues such as diarrhea, pneumonia, bronchitis, septic shock, and multiple organ failure. Currently, there are no medications available for coronavirus patients, except symptom-relieving drugs. Therefore, SARS-CoV-2 requires the development of effective drugs and specific treatments. Heterocycles are important constituents of more than 85% of the physiologically active pharmaceutical drugs on the market now. Several FDA-approved drugs have been reported including molnupiravir, remdesivir, ritonavir, oseltamivir, favipiravir, chloroquine, and hydroxychloroquine for the cure of COVID-19. In this study, we discuss potent anti-SARS-CoV-2 heterocyclic compounds that have been synthesized over the past few years. These compounds included; indole, piperidine, pyrazine, pyrimidine, pyrrole, piperazine, quinazoline, oxazole, quinoline, isoxazole, thiazole, quinoxaline, pyrazole, azafluorene, imidazole, thiadiazole, triazole, coumarin, chromene, and benzodioxole. Both in vitro and in silico studies were performed to determine the potential of these heterocyclic compounds in the fight against various SARS-CoV-2 proteins.

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Crystal structure, DFT studies, Hirshfeld surface and energy framework analysis of 4-(5-nitro-thiophen-2-yl)-pyrrolo [1, 2-a] quinoxaline: A potential SARS-CoV-2 main protease inhibitor

Cited by 15 publications

References 45 publications

Methodology-Centered Review of Molecular Modeling, Simulation, and Prediction of SARS-CoV-2

Methodology-Centered Review of Molecular Modeling, Simulation, and Prediction of SARS-CoV-2

A Review on Multipurpose Potential of Bioactive Heterocycle Quinoxaline

A Comprehensive Update of Anti-COVID-19 Activity of Heterocyclic Compounds

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