Potential COVID-19 Drug Candidates Based on Diazinyl-Thiazol-Imine Moieties: Synthesis and Greener Pastures Biological Study
A novel series of 1-aryl-<i>N</i>-[4-phenyl-5-(arylazo)thiazol-2-yl)methanimines has been synthesized via the condensation of 2-amino-4-phenyl-5-arylazothiazole with various aromatic aldehydes. The synthesized imines were characterized by spectroscopic techniques, namely <sup>1<...
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| Format: | Article |
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MDPI AG
2022-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/2/488 |
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| author | Sraa Abu-Melha Mastoura Mohamed Edrees Musa A. Said Sayed M. Riyadh Nadia S. Al-Kaff Sobhi M. Gomha |
| author_facet | Sraa Abu-Melha Mastoura Mohamed Edrees Musa A. Said Sayed M. Riyadh Nadia S. Al-Kaff Sobhi M. Gomha |
| author_sort | Sraa Abu-Melha |
| collection | DOAJ |
| description | A novel series of 1-aryl-<i>N</i>-[4-phenyl-5-(arylazo)thiazol-2-yl)methanimines has been synthesized via the condensation of 2-amino-4-phenyl-5-arylazothiazole with various aromatic aldehydes. The synthesized imines were characterized by spectroscopic techniques, namely <sup>1</sup>H and <sup>13</sup>C-NMR, FTIR, MS, and Elemental Analysis. A molecular comparative docking study for <b>3a–f</b> was calculated, with reference to two approved drugs, Molnupiravir and Remdesivir, using 7BQY (M<sup>pro</sup>; PDB code 7BQY; resolution: 1.7 A°) under identical conditions. The binding scores against 7BQY were in the range of −7.7 to −8.7 kcal/mol for <b>3a–f</b>. The high scores of the compounds indicated an enhanced binding affinity of the molecules to the receptor. This is due to the hydrophobic interactions and multi-hydrogen bonds between <b>3a–f</b> ligands and the receptor’s active amino acid residues. The main aim of using in silco molecular docking was to rank <b>3a–f</b> with respect to the approved drugs, Molnupiravir and Remdesivir, using free energy methods as greener pastures. A further interesting comparison presented the laydown of the ligands before and after molecular docking. These results and other supporting statistical analyses suggested that ligands <b>3a–f</b> deserve further investigation in the context of potential therapeutic agents for COVID-19. Free-cost, PASS, SwissADME, and Way2drug were used in this research paper to determine the possible biological activities and cytotoxicity of <b>3a–f</b>. |
| first_indexed | 2024-03-10T00:49:45Z |
| format | Article |
| id | doaj.art-2afb4ec0b08b496991670af67444593c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T00:49:45Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2afb4ec0b08b496991670af67444593c2023-11-23T14:52:41ZengMDPI AGMolecules1420-30492022-01-0127248810.3390/molecules27020488Potential COVID-19 Drug Candidates Based on Diazinyl-Thiazol-Imine Moieties: Synthesis and Greener Pastures Biological StudySraa Abu-Melha0Mastoura Mohamed Edrees1Musa A. Said2Sayed M. Riyadh3Nadia S. Al-Kaff4Sobhi M. Gomha5Department of Chemistry, Faculty of Science, King Khalid University, Abha 61413, Saudi ArabiaDepartment of Chemistry, Faculty of Science, King Khalid University, Abha 61413, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi ArabiaDepartment of Biology, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Cairo University, Giza 12613, EgyptA novel series of 1-aryl-<i>N</i>-[4-phenyl-5-(arylazo)thiazol-2-yl)methanimines has been synthesized via the condensation of 2-amino-4-phenyl-5-arylazothiazole with various aromatic aldehydes. The synthesized imines were characterized by spectroscopic techniques, namely <sup>1</sup>H and <sup>13</sup>C-NMR, FTIR, MS, and Elemental Analysis. A molecular comparative docking study for <b>3a–f</b> was calculated, with reference to two approved drugs, Molnupiravir and Remdesivir, using 7BQY (M<sup>pro</sup>; PDB code 7BQY; resolution: 1.7 A°) under identical conditions. The binding scores against 7BQY were in the range of −7.7 to −8.7 kcal/mol for <b>3a–f</b>. The high scores of the compounds indicated an enhanced binding affinity of the molecules to the receptor. This is due to the hydrophobic interactions and multi-hydrogen bonds between <b>3a–f</b> ligands and the receptor’s active amino acid residues. The main aim of using in silco molecular docking was to rank <b>3a–f</b> with respect to the approved drugs, Molnupiravir and Remdesivir, using free energy methods as greener pastures. A further interesting comparison presented the laydown of the ligands before and after molecular docking. These results and other supporting statistical analyses suggested that ligands <b>3a–f</b> deserve further investigation in the context of potential therapeutic agents for COVID-19. Free-cost, PASS, SwissADME, and Way2drug were used in this research paper to determine the possible biological activities and cytotoxicity of <b>3a–f</b>.https://www.mdpi.com/1420-3049/27/2/488imines-tethered thiazolessynthesisCOVID-19in silico molecular dockingmolnupiravirremdesivir |
| spellingShingle | Sraa Abu-Melha Mastoura Mohamed Edrees Musa A. Said Sayed M. Riyadh Nadia S. Al-Kaff Sobhi M. Gomha Potential COVID-19 Drug Candidates Based on Diazinyl-Thiazol-Imine Moieties: Synthesis and Greener Pastures Biological Study Molecules imines-tethered thiazoles synthesis COVID-19 in silico molecular docking molnupiravir remdesivir |
| title | Potential COVID-19 Drug Candidates Based on Diazinyl-Thiazol-Imine Moieties: Synthesis and Greener Pastures Biological Study |
| title_full | Potential COVID-19 Drug Candidates Based on Diazinyl-Thiazol-Imine Moieties: Synthesis and Greener Pastures Biological Study |
| title_fullStr | Potential COVID-19 Drug Candidates Based on Diazinyl-Thiazol-Imine Moieties: Synthesis and Greener Pastures Biological Study |
| title_full_unstemmed | Potential COVID-19 Drug Candidates Based on Diazinyl-Thiazol-Imine Moieties: Synthesis and Greener Pastures Biological Study |
| title_short | Potential COVID-19 Drug Candidates Based on Diazinyl-Thiazol-Imine Moieties: Synthesis and Greener Pastures Biological Study |
| title_sort | potential covid 19 drug candidates based on diazinyl thiazol imine moieties synthesis and greener pastures biological study |
| topic | imines-tethered thiazoles synthesis COVID-19 in silico molecular docking molnupiravir remdesivir |
| url | https://www.mdpi.com/1420-3049/27/2/488 |
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