Synthesis, spectral characterization, crystal structure and computational investigation of 2-formyl-6-methoxy-3-carbethoxy quinoline as potential SARS-CoV inhibitor

A. Franklin Ebenazer; M. Saravanabhavan; K.S. Ramesh; Shabbir Muhammad; Abdullah G. Al-Sehemi; N. Sampathkumar

doi:10.1016/j.jpcs.2022.110886

Synthesis, spectral characterization, crystal structure and computational investigation of 2-formyl-6-methoxy-3-carbethoxy quinoline as potential SARS-CoV inhibitor

A. Franklin Ebenazer, M. Saravanabhavan, K.S. Ramesh, Shabbir Muhammad, Abdullah G. Al-Sehemi, N. Sampathkumar

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

The recent COVID-19 outbreak caused by the novel coronavirus SARS-CoV-2 has an immense impact on global health and economy. Although vaccines are being used, urgent need of drugs based on natural products with high efficacy and safety is a pressing priority. Quinoline alkaloids are well known for their therapeutic action against malaria; initially, it was tried against Coronaviruses. It is a basic vital scaffold to design drugs with required biological and pharmacological activities. In this present study, a new quinoline compound was synthesized and characterized by spectroscopy techniques. Crystal structure was established by SCXRD analysis and data is used as an input to perform various computations. Additionally, using state-of-the-art quantum computational techniques, the geometry optimization and calculation of UV–Vis spectrum of 2F6M3CQ were performed at B3LYP/6-311G* level of theory. The optimized molecular geometric parameters as well as UV–Vis spectrum values are found to be in good agreement with their respective experimental results. The visualization of 3-D plots of FMO and MEP indicated the structure and reactivity trends of 2F6M3CQ molecule. Molecular docking methods were utilized to find the drug ability of 2F6M3CQ with Mproprotein of SARS-CoV-2. There were many intermolecular interactions between Mpro protein and 2F6M3CQ molecule which lead to good binding energy (−5.5 kcal/mol) between them which was found to be better than the binding energy of chloroquinine molecule (−4.5 kcal/mol) as studied under same docking protocols. Finally, drug likeness and ADME properties of 2F6M3CQ were also analyzed. There is no violation found for RO5 in our 2F6M3CQ compound. ADME analysis shows drug like properties of compound 2F6M3CQ which predicts that it might be a potential candidate for inhibition of SARS-CoV-2.

Original language	English (US)
Pages (from-to)	110886
Journal	The Journal of physics and chemistry of solids
Volume	170
DOIs	https://doi.org/10.1016/j.jpcs.2022.110886
State	Published - Jul 16 2022
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2022-09-14
Acknowledgements: The authors from Chikkanna Government Arts College would like to acknowledge, STIC Kochi, India for single crystal x-ray diffraction analysis, Bharathiyar University, Coimbatore, India for IR and NMR spectral analysis. The authors from Ramakrishna Vidhyalaya Arts and Science College acknowledge, Karunya Deemed University, Coimbatore, India for UV–visible–NIR spectral analysis. The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding the work through the Research Project (RGP.1/318/43). For computer time, this research used the resources of the Supercomputing Laboratory at King Abdullah University of Science & Technology (KAUST) in Thuwal, Saudi Arabia.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

ASJC Scopus subject areas

General Materials Science
General Chemistry
Condensed Matter Physics

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.jpcs.2022.110886

Cite this

Franklin Ebenazer, A., Saravanabhavan, M., Ramesh, K. S., Muhammad, S., Al-Sehemi, A. G., & Sampathkumar, N. (2022). Synthesis, spectral characterization, crystal structure and computational investigation of 2-formyl-6-methoxy-3-carbethoxy quinoline as potential SARS-CoV inhibitor. The Journal of physics and chemistry of solids, 170, 110886. https://doi.org/10.1016/j.jpcs.2022.110886

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title = "Synthesis, spectral characterization, crystal structure and computational investigation of 2-formyl-6-methoxy-3-carbethoxy quinoline as potential SARS-CoV inhibitor",

abstract = "The recent COVID-19 outbreak caused by the novel coronavirus SARS-CoV-2 has an immense impact on global health and economy. Although vaccines are being used, urgent need of drugs based on natural products with high efficacy and safety is a pressing priority. Quinoline alkaloids are well known for their therapeutic action against malaria; initially, it was tried against Coronaviruses. It is a basic vital scaffold to design drugs with required biological and pharmacological activities. In this present study, a new quinoline compound was synthesized and characterized by spectroscopy techniques. Crystal structure was established by SCXRD analysis and data is used as an input to perform various computations. Additionally, using state-of-the-art quantum computational techniques, the geometry optimization and calculation of UV–Vis spectrum of 2F6M3CQ were performed at B3LYP/6-311G* level of theory. The optimized molecular geometric parameters as well as UV–Vis spectrum values are found to be in good agreement with their respective experimental results. The visualization of 3-D plots of FMO and MEP indicated the structure and reactivity trends of 2F6M3CQ molecule. Molecular docking methods were utilized to find the drug ability of 2F6M3CQ with Mproprotein of SARS-CoV-2. There were many intermolecular interactions between Mpro protein and 2F6M3CQ molecule which lead to good binding energy (−5.5 kcal/mol) between them which was found to be better than the binding energy of chloroquinine molecule (−4.5 kcal/mol) as studied under same docking protocols. Finally, drug likeness and ADME properties of 2F6M3CQ were also analyzed. There is no violation found for RO5 in our 2F6M3CQ compound. ADME analysis shows drug like properties of compound 2F6M3CQ which predicts that it might be a potential candidate for inhibition of SARS-CoV-2.",

author = "{Franklin Ebenazer}, A. and M. Saravanabhavan and K.S. Ramesh and Shabbir Muhammad and Al-Sehemi, {Abdullah G.} and N. Sampathkumar",

note = "KAUST Repository Item: Exported on 2022-09-14 Acknowledgements: The authors from Chikkanna Government Arts College would like to acknowledge, STIC Kochi, India for single crystal x-ray diffraction analysis, Bharathiyar University, Coimbatore, India for IR and NMR spectral analysis. The authors from Ramakrishna Vidhyalaya Arts and Science College acknowledge, Karunya Deemed University, Coimbatore, India for UV–visible–NIR spectral analysis. The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding the work through the Research Project (RGP.1/318/43). For computer time, this research used the resources of the Supercomputing Laboratory at King Abdullah University of Science & Technology (KAUST) in Thuwal, Saudi Arabia. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

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doi = "10.1016/j.jpcs.2022.110886",

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Franklin Ebenazer, A, Saravanabhavan, M, Ramesh, KS, Muhammad, S, Al-Sehemi, AG & Sampathkumar, N 2022, 'Synthesis, spectral characterization, crystal structure and computational investigation of 2-formyl-6-methoxy-3-carbethoxy quinoline as potential SARS-CoV inhibitor', The Journal of physics and chemistry of solids, vol. 170, pp. 110886. https://doi.org/10.1016/j.jpcs.2022.110886

Synthesis, spectral characterization, crystal structure and computational investigation of 2-formyl-6-methoxy-3-carbethoxy quinoline as potential SARS-CoV inhibitor. / Franklin Ebenazer, A.; Saravanabhavan, M.; Ramesh, K.S. et al.
In: The Journal of physics and chemistry of solids, Vol. 170, 16.07.2022, p. 110886.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis, spectral characterization, crystal structure and computational investigation of 2-formyl-6-methoxy-3-carbethoxy quinoline as potential SARS-CoV inhibitor

AU - Franklin Ebenazer, A.

AU - Saravanabhavan, M.

AU - Ramesh, K.S.

AU - Muhammad, Shabbir

AU - Al-Sehemi, Abdullah G.

AU - Sampathkumar, N.

N1 - KAUST Repository Item: Exported on 2022-09-14 Acknowledgements: The authors from Chikkanna Government Arts College would like to acknowledge, STIC Kochi, India for single crystal x-ray diffraction analysis, Bharathiyar University, Coimbatore, India for IR and NMR spectral analysis. The authors from Ramakrishna Vidhyalaya Arts and Science College acknowledge, Karunya Deemed University, Coimbatore, India for UV–visible–NIR spectral analysis. The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding the work through the Research Project (RGP.1/318/43). For computer time, this research used the resources of the Supercomputing Laboratory at King Abdullah University of Science & Technology (KAUST) in Thuwal, Saudi Arabia. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2022/7/16

Y1 - 2022/7/16

N2 - The recent COVID-19 outbreak caused by the novel coronavirus SARS-CoV-2 has an immense impact on global health and economy. Although vaccines are being used, urgent need of drugs based on natural products with high efficacy and safety is a pressing priority. Quinoline alkaloids are well known for their therapeutic action against malaria; initially, it was tried against Coronaviruses. It is a basic vital scaffold to design drugs with required biological and pharmacological activities. In this present study, a new quinoline compound was synthesized and characterized by spectroscopy techniques. Crystal structure was established by SCXRD analysis and data is used as an input to perform various computations. Additionally, using state-of-the-art quantum computational techniques, the geometry optimization and calculation of UV–Vis spectrum of 2F6M3CQ were performed at B3LYP/6-311G* level of theory. The optimized molecular geometric parameters as well as UV–Vis spectrum values are found to be in good agreement with their respective experimental results. The visualization of 3-D plots of FMO and MEP indicated the structure and reactivity trends of 2F6M3CQ molecule. Molecular docking methods were utilized to find the drug ability of 2F6M3CQ with Mproprotein of SARS-CoV-2. There were many intermolecular interactions between Mpro protein and 2F6M3CQ molecule which lead to good binding energy (−5.5 kcal/mol) between them which was found to be better than the binding energy of chloroquinine molecule (−4.5 kcal/mol) as studied under same docking protocols. Finally, drug likeness and ADME properties of 2F6M3CQ were also analyzed. There is no violation found for RO5 in our 2F6M3CQ compound. ADME analysis shows drug like properties of compound 2F6M3CQ which predicts that it might be a potential candidate for inhibition of SARS-CoV-2.

AB - The recent COVID-19 outbreak caused by the novel coronavirus SARS-CoV-2 has an immense impact on global health and economy. Although vaccines are being used, urgent need of drugs based on natural products with high efficacy and safety is a pressing priority. Quinoline alkaloids are well known for their therapeutic action against malaria; initially, it was tried against Coronaviruses. It is a basic vital scaffold to design drugs with required biological and pharmacological activities. In this present study, a new quinoline compound was synthesized and characterized by spectroscopy techniques. Crystal structure was established by SCXRD analysis and data is used as an input to perform various computations. Additionally, using state-of-the-art quantum computational techniques, the geometry optimization and calculation of UV–Vis spectrum of 2F6M3CQ were performed at B3LYP/6-311G* level of theory. The optimized molecular geometric parameters as well as UV–Vis spectrum values are found to be in good agreement with their respective experimental results. The visualization of 3-D plots of FMO and MEP indicated the structure and reactivity trends of 2F6M3CQ molecule. Molecular docking methods were utilized to find the drug ability of 2F6M3CQ with Mproprotein of SARS-CoV-2. There were many intermolecular interactions between Mpro protein and 2F6M3CQ molecule which lead to good binding energy (−5.5 kcal/mol) between them which was found to be better than the binding energy of chloroquinine molecule (−4.5 kcal/mol) as studied under same docking protocols. Finally, drug likeness and ADME properties of 2F6M3CQ were also analyzed. There is no violation found for RO5 in our 2F6M3CQ compound. ADME analysis shows drug like properties of compound 2F6M3CQ which predicts that it might be a potential candidate for inhibition of SARS-CoV-2.

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DO - 10.1016/j.jpcs.2022.110886

M3 - Article

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SN - 0022-3697

VL - 170

SP - 110886

JO - The Journal of physics and chemistry of solids

JF - The Journal of physics and chemistry of solids

ER -

Synthesis, spectral characterization, crystal structure and computational investigation of 2-formyl-6-methoxy-3-carbethoxy quinoline as potential SARS-CoV inhibitor

Abstract

Bibliographical note

ASJC Scopus subject areas

UN SDGs

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