Novel 1,2,3-Triazole-Based Benzothiazole Derivatives: Efficient Synthesis, DFT, Molecular Docking, and ADMET Studies
A new series of 1,2,3-triazole derivatives <b>5a</b>–<b>f</b> based on benzothiazole were synthesized by the 1,3-dipolar cycloaddition reaction of S-propargyl mercaptobenzothiazole and α-halo ester/amide in moderate to good yields (47–75%). The structure of all products was c...
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MDPI AG
2022-12-01
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| author | Zohreh Mirjafary Mahdieh Mohammad Karbasi Parsa Hesamzadeh Hamid Reza Shaker Asghar Amiri Hamid Saeidian |
| author_facet | Zohreh Mirjafary Mahdieh Mohammad Karbasi Parsa Hesamzadeh Hamid Reza Shaker Asghar Amiri Hamid Saeidian |
| author_sort | Zohreh Mirjafary |
| collection | DOAJ |
| description | A new series of 1,2,3-triazole derivatives <b>5a</b>–<b>f</b> based on benzothiazole were synthesized by the 1,3-dipolar cycloaddition reaction of S-propargyl mercaptobenzothiazole and α-halo ester/amide in moderate to good yields (47–75%). The structure of all products was characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and CHN elemental data. This protocol is easy and green and proceeds under mild and green reaction conditions with available starting materials. The structural and electronic analysis and <sup>1</sup>H and <sup>13</sup>C chemical shifts of the characterized structure of <b>5e</b> were also calculated by applying the B3LYP/6-31 + G(d, <i>p</i>) level of density functional theory (DFT) method. In the final section, all the synthesized compounds were evaluated for their anti-inflammatory activity by biochemical COX-2 inhibition, antifungal inhibition with CYP51, anti-tuberculosis target protein ENR, DPRE1, pks13, and Thymidylate kinase by molecular docking studies. The ADMET analysis of the molecules <b>5a</b>–<b>f</b> revealed that <b>5d</b> and <b>5a</b> are the most-promising drug-like molecules out of the six synthesized molecules. |
| first_indexed | 2024-03-09T17:39:12Z |
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| id | doaj.art-e988b612dc064ebda46caa161ae98c19 |
| institution | Directory Open Access Journal |
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| language | English |
| last_indexed | 2024-03-09T17:39:12Z |
| publishDate | 2022-12-01 |
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| series | Molecules |
| spelling | doaj.art-e988b612dc064ebda46caa161ae98c192023-11-24T11:44:10ZengMDPI AGMolecules1420-30492022-12-012723855510.3390/molecules27238555Novel 1,2,3-Triazole-Based Benzothiazole Derivatives: Efficient Synthesis, DFT, Molecular Docking, and ADMET StudiesZohreh Mirjafary0Mahdieh Mohammad Karbasi1Parsa Hesamzadeh2Hamid Reza Shaker3Asghar Amiri4Hamid Saeidian5Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran 14515-775, IranDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran 14515-775, IranDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran 14515-775, IranDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran 14515-775, IranDepartment of Science, Payame Noor University (PNU), Tehran P.O. Box 19395-4697, IranDepartment of Science, Payame Noor University (PNU), Tehran P.O. Box 19395-4697, IranA new series of 1,2,3-triazole derivatives <b>5a</b>–<b>f</b> based on benzothiazole were synthesized by the 1,3-dipolar cycloaddition reaction of S-propargyl mercaptobenzothiazole and α-halo ester/amide in moderate to good yields (47–75%). The structure of all products was characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and CHN elemental data. This protocol is easy and green and proceeds under mild and green reaction conditions with available starting materials. The structural and electronic analysis and <sup>1</sup>H and <sup>13</sup>C chemical shifts of the characterized structure of <b>5e</b> were also calculated by applying the B3LYP/6-31 + G(d, <i>p</i>) level of density functional theory (DFT) method. In the final section, all the synthesized compounds were evaluated for their anti-inflammatory activity by biochemical COX-2 inhibition, antifungal inhibition with CYP51, anti-tuberculosis target protein ENR, DPRE1, pks13, and Thymidylate kinase by molecular docking studies. The ADMET analysis of the molecules <b>5a</b>–<b>f</b> revealed that <b>5d</b> and <b>5a</b> are the most-promising drug-like molecules out of the six synthesized molecules.https://www.mdpi.com/1420-3049/27/23/85551,2,3-triazoleclick reactioncycloadditionDFT calculationmolecular dockingADMET study |
| spellingShingle | Zohreh Mirjafary Mahdieh Mohammad Karbasi Parsa Hesamzadeh Hamid Reza Shaker Asghar Amiri Hamid Saeidian Novel 1,2,3-Triazole-Based Benzothiazole Derivatives: Efficient Synthesis, DFT, Molecular Docking, and ADMET Studies Molecules 1,2,3-triazole click reaction cycloaddition DFT calculation molecular docking ADMET study |
| title | Novel 1,2,3-Triazole-Based Benzothiazole Derivatives: Efficient Synthesis, DFT, Molecular Docking, and ADMET Studies |
| title_full | Novel 1,2,3-Triazole-Based Benzothiazole Derivatives: Efficient Synthesis, DFT, Molecular Docking, and ADMET Studies |
| title_fullStr | Novel 1,2,3-Triazole-Based Benzothiazole Derivatives: Efficient Synthesis, DFT, Molecular Docking, and ADMET Studies |
| title_full_unstemmed | Novel 1,2,3-Triazole-Based Benzothiazole Derivatives: Efficient Synthesis, DFT, Molecular Docking, and ADMET Studies |
| title_short | Novel 1,2,3-Triazole-Based Benzothiazole Derivatives: Efficient Synthesis, DFT, Molecular Docking, and ADMET Studies |
| title_sort | novel 1 2 3 triazole based benzothiazole derivatives efficient synthesis dft molecular docking and admet studies |
| topic | 1,2,3-triazole click reaction cycloaddition DFT calculation molecular docking ADMET study |
| url | https://www.mdpi.com/1420-3049/27/23/8555 |
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