New quinoline-triazole conjugates: Synthesis, and antiviral properties against SARS-CoV-2

Israa A. Seliem; Siva S. Panda; Adel S. Girgis; Yassmin Moatasim; Ahmed Kandeil; Ahmed Mostafa; Mohamed A. Ali; Eman S. Nossier; Fatma Rasslan; Aladdin M. Srour; Rajeev Sakhuja; Tarek S. Ibrahim; Zakaria K.M. Abdel-samii; Amany M.M. Al-Mahmoudy

doi:10.1016/j.bioorg.2021.105117

New quinoline-triazole conjugates: Synthesis, and antiviral properties against SARS-CoV-2

Israa A. Seliem, Siva S. Panda, Adel S. Girgis, Yassmin Moatasim, Ahmed Kandeil, Ahmed Mostafa, Mohamed A. Ali, Eman S. Nossier, Fatma Rasslan, Aladdin M. Srour, Rajeev Sakhuja, Tarek S. Ibrahim, Zakaria K.M. Abdel-samii, Amany M.M. Al-Mahmoudy

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

44 Scopus citations

Abstract

At present therapeutic options for severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) are very limited. We designed and synthesized three sets of small molecules using quinoline scaffolds. A series of quinoline conjugates (10a-l, 11a-c, and 12a-e) by incorporating 1,2,3-triazole were synthesized via a modified microwave-assisted click chemistry technique. Among the synthesized conjugates, 4-((1-(2-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-6-fluoro-2-(trifluoromethyl)quinoline (10g) and 6-fluoro-4-(2-(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)ethoxy)-2-(trifluoromethyl)quinoline (12c) show high potency against SARS-CoV-2. The selectivity index (SI) of compounds 10g and 12c also indicates the significant efficacy compared to the reference drugs.

Original language	English (US)
Article number	105117
Journal	Bioorganic Chemistry
Volume	114
DOIs	https://doi.org/10.1016/j.bioorg.2021.105117
State	Published - Sep 2021

Keywords

Click chemistry
Molecular docking
Quinoline
SARS-CoV-2
Triazole

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Drug Discovery
Organic Chemistry

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Seliem, I. A., Panda, S. S., Girgis, A. S., Moatasim, Y., Kandeil, A., Mostafa, A., Ali, M. A., Nossier, E. S., Rasslan, F., Srour, A. M., Sakhuja, R., Ibrahim, T. S., Abdel-samii, Z. K. M., & Al-Mahmoudy, A. M. M. (2021). New quinoline-triazole conjugates: Synthesis, and antiviral properties against SARS-CoV-2. Bioorganic Chemistry, 114, Article 105117. https://doi.org/10.1016/j.bioorg.2021.105117

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title = "New quinoline-triazole conjugates: Synthesis, and antiviral properties against SARS-CoV-2",

abstract = "At present therapeutic options for severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) are very limited. We designed and synthesized three sets of small molecules using quinoline scaffolds. A series of quinoline conjugates (10a-l, 11a-c, and 12a-e) by incorporating 1,2,3-triazole were synthesized via a modified microwave-assisted click chemistry technique. Among the synthesized conjugates, 4-((1-(2-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-6-fluoro-2-(trifluoromethyl)quinoline (10g) and 6-fluoro-4-(2-(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)ethoxy)-2-(trifluoromethyl)quinoline (12c) show high potency against SARS-CoV-2. The selectivity index (SI) of compounds 10g and 12c also indicates the significant efficacy compared to the reference drugs.",

keywords = "Click chemistry, Molecular docking, Quinoline, SARS-CoV-2, Triazole",

author = "Seliem, {Israa A.} and Panda, {Siva S.} and Girgis, {Adel S.} and Yassmin Moatasim and Ahmed Kandeil and Ahmed Mostafa and Ali, {Mohamed A.} and Nossier, {Eman S.} and Fatma Rasslan and Srour, {Aladdin M.} and Rajeev Sakhuja and Ibrahim, {Tarek S.} and Abdel-samii, {Zakaria K.M.} and Al-Mahmoudy, {Amany M.M.}",

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year = "2021",

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doi = "10.1016/j.bioorg.2021.105117",

language = "English (US)",

volume = "114",

journal = "Bioorganic Chemistry",

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T2 - Synthesis, and antiviral properties against SARS-CoV-2

AU - Seliem, Israa A.

AU - Panda, Siva S.

AU - Girgis, Adel S.

AU - Moatasim, Yassmin

AU - Kandeil, Ahmed

AU - Mostafa, Ahmed

AU - Ali, Mohamed A.

AU - Nossier, Eman S.

AU - Rasslan, Fatma

AU - Srour, Aladdin M.

AU - Sakhuja, Rajeev

AU - Ibrahim, Tarek S.

AU - Abdel-samii, Zakaria K.M.

AU - Al-Mahmoudy, Amany M.M.

PY - 2021/9

Y1 - 2021/9

N2 - At present therapeutic options for severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) are very limited. We designed and synthesized three sets of small molecules using quinoline scaffolds. A series of quinoline conjugates (10a-l, 11a-c, and 12a-e) by incorporating 1,2,3-triazole were synthesized via a modified microwave-assisted click chemistry technique. Among the synthesized conjugates, 4-((1-(2-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-6-fluoro-2-(trifluoromethyl)quinoline (10g) and 6-fluoro-4-(2-(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)ethoxy)-2-(trifluoromethyl)quinoline (12c) show high potency against SARS-CoV-2. The selectivity index (SI) of compounds 10g and 12c also indicates the significant efficacy compared to the reference drugs.

AB - At present therapeutic options for severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) are very limited. We designed and synthesized three sets of small molecules using quinoline scaffolds. A series of quinoline conjugates (10a-l, 11a-c, and 12a-e) by incorporating 1,2,3-triazole were synthesized via a modified microwave-assisted click chemistry technique. Among the synthesized conjugates, 4-((1-(2-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-6-fluoro-2-(trifluoromethyl)quinoline (10g) and 6-fluoro-4-(2-(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)ethoxy)-2-(trifluoromethyl)quinoline (12c) show high potency against SARS-CoV-2. The selectivity index (SI) of compounds 10g and 12c also indicates the significant efficacy compared to the reference drugs.

KW - Click chemistry

KW - Molecular docking

KW - Quinoline

KW - SARS-CoV-2

KW - Triazole

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JO - Bioorganic Chemistry

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New quinoline-triazole conjugates: Synthesis, and antiviral properties against SARS-CoV-2

Abstract

Keywords

ASJC Scopus subject areas

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