Synthesis of Novel Benzothiazole–Profen Hybrid Amides as Potential NSAID Candidates
Herein, we report the synthesis of a series of new compounds by combining 2-aminobenzothiazole with various profens. The compounds were characterized using techniques such as <sup>1</sup>H- and <sup>13</sup>C-NMR, FT-IR spectrometry, and high-resolution mass spectrometry (HRM...
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2024-12-01
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| author | Iliyan Ivanov Stanimir Manolov Dimitar Bojilov Yordan Stremski Gabriel Marc Stela Statkova-Abeghe Smaranda Oniga Ovidiu Oniga Paraskev Nedialkov |
| author_facet | Iliyan Ivanov Stanimir Manolov Dimitar Bojilov Yordan Stremski Gabriel Marc Stela Statkova-Abeghe Smaranda Oniga Ovidiu Oniga Paraskev Nedialkov |
| author_sort | Iliyan Ivanov |
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| description | Herein, we report the synthesis of a series of new compounds by combining 2-aminobenzothiazole with various profens. The compounds were characterized using techniques such as <sup>1</sup>H- and <sup>13</sup>C-NMR, FT-IR spectrometry, and high-resolution mass spectrometry (HRMS), with detailed HRMS analysis conducted for each molecule. Their biological activities were tested in vitro, revealing significant anti-inflammatory and antioxidant effects, comparable to those of standard reference compounds. Lipophilicity was experimentally determined through partition coefficient (R<sub>M</sub>) measurements. To understand their binding affinity, molecular docking studies were perfsormed to analyze interactions with human serum albumin (HSA). The stability of these predicted complexes was further evaluated through molecular dynamics simulations. The results highlight the compounds’ promising biological activity and strong affinity for HSA. The new hybrid molecule between 2-ABT and ketoprofen <b>3b</b> demonstrates significant promise based on the experimental data and is further supported by in silico calculations. Compound <b>3b</b> exhibits the best hydrogen peroxide scavenging activity among the tested compounds, with an IC<sub>50</sub> of 60.24 μg/mL. Furthermore, <b>3b</b> also displays superior anti-inflammatory activity, with an IC<sub>50</sub> of 54.64 μg/mL, making it more effective than the standard ibuprofen (76.05 μg/mL). |
| format | Article |
| id | doaj-art-35c95284e19247a4a5f7366599a3e9f9 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-35c95284e19247a4a5f7366599a3e9f92025-01-10T13:18:54ZengMDPI AGMolecules1420-30492024-12-0130110710.3390/molecules30010107Synthesis of Novel Benzothiazole–Profen Hybrid Amides as Potential NSAID CandidatesIliyan Ivanov0Stanimir Manolov1Dimitar Bojilov2Yordan Stremski3Gabriel Marc4Stela Statkova-Abeghe5Smaranda Oniga6Ovidiu Oniga7Paraskev Nedialkov8Department of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 24 “Tsar Assen” Str., 4000 Plovdiv, BulgariaDepartment of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 24 “Tsar Assen” Str., 4000 Plovdiv, BulgariaDepartment of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 24 “Tsar Assen” Str., 4000 Plovdiv, BulgariaDepartment of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 24 “Tsar Assen” Str., 4000 Plovdiv, BulgariaDepartment of Organic Chemistry, Faculty of Pharmacy, “Iuliu Hațieganu” University of Medicine and Pharmacy, 41 Victor Babeș Street, RO-400010 Cluj-Napoca, RomaniaDepartment of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 24 “Tsar Assen” Str., 4000 Plovdiv, BulgariaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, “Iuliu Hațieganu” University of Medicine and Pharmacy, 41 Victor Babeș Street, RO-400010 Cluj-Napoca, RomaniaDepartment of Therapeutic Chemistry, “Iuliu Hațieganu” University of Medicine and Pharmacy, 12 Ion Creangă Street, RO-400010 Cluj-Napoca, RomaniaDepartment of Pharmacognosy, Faculty of Pharmacy, Medical University of Sofia, 2 Dunav Street, 1000 Sofia, BulgariaHerein, we report the synthesis of a series of new compounds by combining 2-aminobenzothiazole with various profens. The compounds were characterized using techniques such as <sup>1</sup>H- and <sup>13</sup>C-NMR, FT-IR spectrometry, and high-resolution mass spectrometry (HRMS), with detailed HRMS analysis conducted for each molecule. Their biological activities were tested in vitro, revealing significant anti-inflammatory and antioxidant effects, comparable to those of standard reference compounds. Lipophilicity was experimentally determined through partition coefficient (R<sub>M</sub>) measurements. To understand their binding affinity, molecular docking studies were perfsormed to analyze interactions with human serum albumin (HSA). The stability of these predicted complexes was further evaluated through molecular dynamics simulations. The results highlight the compounds’ promising biological activity and strong affinity for HSA. The new hybrid molecule between 2-ABT and ketoprofen <b>3b</b> demonstrates significant promise based on the experimental data and is further supported by in silico calculations. Compound <b>3b</b> exhibits the best hydrogen peroxide scavenging activity among the tested compounds, with an IC<sub>50</sub> of 60.24 μg/mL. Furthermore, <b>3b</b> also displays superior anti-inflammatory activity, with an IC<sub>50</sub> of 54.64 μg/mL, making it more effective than the standard ibuprofen (76.05 μg/mL).https://www.mdpi.com/1420-3049/30/1/107benzothiazoleprofenshybrid moleculesamidesin vitro biological activitylipophilicity |
| spellingShingle | Iliyan Ivanov Stanimir Manolov Dimitar Bojilov Yordan Stremski Gabriel Marc Stela Statkova-Abeghe Smaranda Oniga Ovidiu Oniga Paraskev Nedialkov Synthesis of Novel Benzothiazole–Profen Hybrid Amides as Potential NSAID Candidates Molecules benzothiazole profens hybrid molecules amides in vitro biological activity lipophilicity |
| title | Synthesis of Novel Benzothiazole–Profen Hybrid Amides as Potential NSAID Candidates |
| title_full | Synthesis of Novel Benzothiazole–Profen Hybrid Amides as Potential NSAID Candidates |
| title_fullStr | Synthesis of Novel Benzothiazole–Profen Hybrid Amides as Potential NSAID Candidates |
| title_full_unstemmed | Synthesis of Novel Benzothiazole–Profen Hybrid Amides as Potential NSAID Candidates |
| title_short | Synthesis of Novel Benzothiazole–Profen Hybrid Amides as Potential NSAID Candidates |
| title_sort | synthesis of novel benzothiazole profen hybrid amides as potential nsaid candidates |
| topic | benzothiazole profens hybrid molecules amides in vitro biological activity lipophilicity |
| url | https://www.mdpi.com/1420-3049/30/1/107 |
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