Synthesis, Molecular Docking, and Dynamic Simulation Targeting Main Protease (Mpro) of New, Thiazole Clubbed Pyridine Scaffolds as Potential COVID-19 Inhibitors
Many biological activities of pyridine and thiazole derivatives have been reported, including antiviral activity and, more recently, as COVID-19 inhibitors. Thus, in this paper, we designed, synthesized, and characterized a novel series of N-aminothiazole-hydrazineethyl-pyridines, beginning with a N...
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| Published in | Current Issues in Molecular Biology Vol. 45; no. 2; pp. 1422 - 1442 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
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MDPI AG
01.02.2023
MDPI |
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| Online Access | Get full text |
| ISSN | 1467-3045 1467-3037 1467-3045 |
| DOI | 10.3390/cimb45020093 |
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| Abstract | Many biological activities of pyridine and thiazole derivatives have been reported, including antiviral activity and, more recently, as COVID-19 inhibitors. Thus, in this paper, we designed, synthesized, and characterized a novel series of N-aminothiazole-hydrazineethyl-pyridines, beginning with a N′-(1-(pyridine-3-yl)ethylidene)hydrazinecarbothiohydrazide derivative and various hydrazonoyl chlorides and phenacyl bromides. Their Schiff bases were prepared from the condensation of N-aminothiazole derivatives with 4-methoxybenzaldehyde. FTIR, MS, NMR, and elemental studies were used to identify new products. The binding energy for non-bonding interactions between the ligand (studied compounds) and receptor was determined using molecular docking against the SARS-CoV-2 main protease (PDB code: 6LU7). Finally, the best docked pose with highest binding energy (8a = −8.6 kcal/mol) was selected for further molecular dynamics (MD) simulation studies to verify the outcomes and comprehend the thermodynamic properties of the binding. Through additional in vitro and in vivo research on the newly synthesized chemicals, it is envisaged that the achieved results will represent a significant advancement in the fight against COVID-19. |
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| AbstractList | Many biological activities of pyridine and thiazole derivatives have been reported, including antiviral activity and, more recently, as COVID-19 inhibitors. Thus, in this paper, we designed, synthesized, and characterized a novel series of
N
-aminothiazole-hydrazineethyl-pyridines, beginning with a
N
′-(1-(pyridine-3-yl)ethylidene)hydrazinecarbothiohydrazide derivative and various hydrazonoyl chlorides and phenacyl bromides. Their Schiff bases were prepared from the condensation of N-aminothiazole derivatives with 4-methoxybenzaldehyde. FTIR, MS, NMR, and elemental studies were used to identify new products. The binding energy for non-bonding interactions between the ligand (studied compounds) and receptor was determined using molecular docking against the SARS-CoV-2 main protease (PDB code: 6LU7). Finally, the best docked pose with highest binding energy (
8a
= −8.6 kcal/mol) was selected for further molecular dynamics (MD) simulation studies to verify the outcomes and comprehend the thermodynamic properties of the binding. Through additional in vitro and in vivo research on the newly synthesized chemicals, it is envisaged that the achieved results will represent a significant advancement in the fight against COVID-19. Many biological activities of pyridine and thiazole derivatives have been reported, including antiviral activity and, more recently, as COVID-19 inhibitors. Thus, in this paper, we designed, synthesized, and characterized a novel series of N-aminothiazole-hydrazineethyl-pyridines, beginning with a N′-(1-(pyridine-3-yl)ethylidene)hydrazinecarbothiohydrazide derivative and various hydrazonoyl chlorides and phenacyl bromides. Their Schiff bases were prepared from the condensation of N-aminothiazole derivatives with 4-methoxybenzaldehyde. FTIR, MS, NMR, and elemental studies were used to identify new products. The binding energy for non-bonding interactions between the ligand (studied compounds) and receptor was determined using molecular docking against the SARS-CoV-2 main protease (PDB code: 6LU7). Finally, the best docked pose with highest binding energy (8a = −8.6 kcal/mol) was selected for further molecular dynamics (MD) simulation studies to verify the outcomes and comprehend the thermodynamic properties of the binding. Through additional in vitro and in vivo research on the newly synthesized chemicals, it is envisaged that the achieved results will represent a significant advancement in the fight against COVID-19. Many biological activities of pyridine and thiazole derivatives have been reported, including antiviral activity and, more recently, as COVID-19 inhibitors. Thus, in this paper, we designed, synthesized, and characterized a novel series of -aminothiazole-hydrazineethyl-pyridines, beginning with a '-(1-(pyridine-3-yl)ethylidene)hydrazinecarbothiohydrazide derivative and various hydrazonoyl chlorides and phenacyl bromides. Their Schiff bases were prepared from the condensation of N-aminothiazole derivatives with 4-methoxybenzaldehyde. FTIR, MS, NMR, and elemental studies were used to identify new products. The binding energy for non-bonding interactions between the ligand (studied compounds) and receptor was determined using molecular docking against the SARS-CoV-2 main protease (PDB code: 6LU7). Finally, the best docked pose with highest binding energy ( = -8.6 kcal/mol) was selected for further molecular dynamics (MD) simulation studies to verify the outcomes and comprehend the thermodynamic properties of the binding. Through additional in vitro and in vivo research on the newly synthesized chemicals, it is envisaged that the achieved results will represent a significant advancement in the fight against COVID-19. Many biological activities of pyridine and thiazole derivatives have been reported, including antiviral activity and, more recently, as COVID-19 inhibitors. Thus, in this paper, we designed, synthesized, and characterized a novel series of N-aminothiazole-hydrazineethyl-pyridines, beginning with a N'-(1-(pyridine-3-yl)ethylidene)hydrazinecarbothiohydrazide derivative and various hydrazonoyl chlorides and phenacyl bromides. Their Schiff bases were prepared from the condensation of N-aminothiazole derivatives with 4-methoxybenzaldehyde. FTIR, MS, NMR, and elemental studies were used to identify new products. The binding energy for non-bonding interactions between the ligand (studied compounds) and receptor was determined using molecular docking against the SARS-CoV-2 main protease (PDB code: 6LU7). Finally, the best docked pose with highest binding energy (8a = -8.6 kcal/mol) was selected for further molecular dynamics (MD) simulation studies to verify the outcomes and comprehend the thermodynamic properties of the binding. Through additional in vitro and in vivo research on the newly synthesized chemicals, it is envisaged that the achieved results will represent a significant advancement in the fight against COVID-19.Many biological activities of pyridine and thiazole derivatives have been reported, including antiviral activity and, more recently, as COVID-19 inhibitors. Thus, in this paper, we designed, synthesized, and characterized a novel series of N-aminothiazole-hydrazineethyl-pyridines, beginning with a N'-(1-(pyridine-3-yl)ethylidene)hydrazinecarbothiohydrazide derivative and various hydrazonoyl chlorides and phenacyl bromides. Their Schiff bases were prepared from the condensation of N-aminothiazole derivatives with 4-methoxybenzaldehyde. FTIR, MS, NMR, and elemental studies were used to identify new products. The binding energy for non-bonding interactions between the ligand (studied compounds) and receptor was determined using molecular docking against the SARS-CoV-2 main protease (PDB code: 6LU7). Finally, the best docked pose with highest binding energy (8a = -8.6 kcal/mol) was selected for further molecular dynamics (MD) simulation studies to verify the outcomes and comprehend the thermodynamic properties of the binding. Through additional in vitro and in vivo research on the newly synthesized chemicals, it is envisaged that the achieved results will represent a significant advancement in the fight against COVID-19. |
| Audience | Academic |
| Author | Alghamdi, Adel Ansari, Mukhtar Gomha, Sobhi M. Alamri, Abdulwahab Abouzied, Amr S. Khadra, Ibrahim Zaki, Yasser H. Anwar, Sirajudheen |
| AuthorAffiliation | 2 Department of Pharmaceutical Chemistry, College of Pharmacy, University of Hail, Hail 81442, Saudi Arabia 9 Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt 1 Pharmaceutical Chemistry Department, Faculty of Clinical Pharmacy, Al Baha University, Al Baha P.O. Box 1988, Saudi Arabia 8 Department of Chemistry, Faculty of Science, Islamic University of Madinah, Madinah 42351, Saudi Arabia 6 Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, UK 3 Department of Pharmaceutical Chemistry, National Organization for Drug Control and Research (NODCAR), Giza 12311, Egypt 5 Department of Clinical Pharmacy, College of Pharmacy, University of Hail, Hail 81442, Saudi Arabia 4 Department of Pharmacology and Toxicology, College of Pharmacy, University of Hail, Hail 81442, Saudi Arabia 7 Department of Chemistry, Faculty of Science, Beni-Suef University, Beni-Suef 62514, Egypt |
| AuthorAffiliation_xml | – name: 8 Department of Chemistry, Faculty of Science, Islamic University of Madinah, Madinah 42351, Saudi Arabia – name: 9 Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt – name: 2 Department of Pharmaceutical Chemistry, College of Pharmacy, University of Hail, Hail 81442, Saudi Arabia – name: 6 Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, UK – name: 7 Department of Chemistry, Faculty of Science, Beni-Suef University, Beni-Suef 62514, Egypt – name: 1 Pharmaceutical Chemistry Department, Faculty of Clinical Pharmacy, Al Baha University, Al Baha P.O. Box 1988, Saudi Arabia – name: 3 Department of Pharmaceutical Chemistry, National Organization for Drug Control and Research (NODCAR), Giza 12311, Egypt – name: 4 Department of Pharmacology and Toxicology, College of Pharmacy, University of Hail, Hail 81442, Saudi Arabia – name: 5 Department of Clinical Pharmacy, College of Pharmacy, University of Hail, Hail 81442, Saudi Arabia |
| Author_xml | – sequence: 1 givenname: Adel orcidid: 0000-0002-8063-0090 surname: Alghamdi fullname: Alghamdi, Adel – sequence: 2 givenname: Amr S. orcidid: 0000-0002-9202-3909 surname: Abouzied fullname: Abouzied, Amr S. – sequence: 3 givenname: Abdulwahab orcidid: 0000-0001-8852-7517 surname: Alamri fullname: Alamri, Abdulwahab – sequence: 4 givenname: Sirajudheen orcidid: 0000-0002-0926-2790 surname: Anwar fullname: Anwar, Sirajudheen – sequence: 5 givenname: Mukhtar orcidid: 0000-0002-5247-6356 surname: Ansari fullname: Ansari, Mukhtar – sequence: 6 givenname: Ibrahim orcidid: 0000-0002-9846-1520 surname: Khadra fullname: Khadra, Ibrahim – sequence: 7 givenname: Yasser H. orcidid: 0000-0002-3502-0445 surname: Zaki fullname: Zaki, Yasser H. – sequence: 8 givenname: Sobhi M. orcidid: 0000-0002-7739-2837 surname: Gomha fullname: Gomha, Sobhi M. |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36826038$$D View this record in MEDLINE/PubMed |
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| Keywords | COVID-19 acetyl pyridines molecular docking schiff bases hydrazonoyl chlorides thiazoles |
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| SubjectTerms | acetyl pyridines Antiviral agents COVID-19 Force and energy Health aspects hydrazonoyl chlorides molecular docking Molecular dynamics Proteases Pyridine Schiff bases Thermodynamics thiazoles |
| Title | Synthesis, Molecular Docking, and Dynamic Simulation Targeting Main Protease (Mpro) of New, Thiazole Clubbed Pyridine Scaffolds as Potential COVID-19 Inhibitors |
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