Synthesis of acetamidosulfonamide derivatives with antioxidative and QSAR studies
A series of sixteen acetamidosulfonamide derivatives (1-16) have been synthesized and investigated for their antioxidant (radical scavenging and superoxide dismutase (SOD)) and antimicrobial activities. Most compounds exhibited antioxidant activities in which compound 15 displayed the most potent ra...
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| Format: | Article |
| Language: | English |
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IfADo - Leibniz Research Centre for Working Environment and Human Factors, Dortmund
2022-02-01
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| Series: | EXCLI Journal : Experimental and Clinical Sciences |
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| Online Access: | https://www.excli.de/index.php/excli/article/view/4590 |
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| author | Apilak Worachartcheewan Somchai Pisutjaroenpong Ratchanok Pingaew Supaluk Prachayasittikul Suphakit Siriwong Somsak Ruchirawat Virapong Prachayasittikul |
| author_facet | Apilak Worachartcheewan Somchai Pisutjaroenpong Ratchanok Pingaew Supaluk Prachayasittikul Suphakit Siriwong Somsak Ruchirawat Virapong Prachayasittikul |
| author_sort | Apilak Worachartcheewan |
| collection | DOAJ |
| description | A series of sixteen acetamidosulfonamide derivatives (1-16) have been synthesized and investigated for their antioxidant (radical scavenging and superoxide dismutase (SOD)) and antimicrobial activities. Most compounds exhibited antioxidant activities in which compound 15 displayed the most potent radical scavenging and SOD activities. Quantitative structure-activity relationship (QSAR) has been studied using multiple linear regression. The constructed QSAR models displayed high correlation coefficient (Q2/Loo-CV= 0.9708 and 0.8753 for RSA and SOD activities, respectively), but low root mean square error (RMSELOO-CV = 0.5105 and 1.3571 for RSA and SOD activities, respectively). The structure-activity relationship showed that an ethylene group connected to pyridine ring provided significant antioxidant activities. The QSAR models give insight into the rational designed of eighty new sulfonamides with various electron donating and withdrawing groups. The top five new designed sulfonamides with nitro group are potential antioxidants to be further developed for medicinal applications. |
| first_indexed | 2024-04-09T17:07:01Z |
| format | Article |
| id | doaj.art-fb2bcd3013e24b0f8c93755fefd544c1 |
| institution | Directory Open Access Journal |
| issn | 1611-2156 |
| language | English |
| last_indexed | 2024-04-09T17:07:01Z |
| publishDate | 2022-02-01 |
| publisher | IfADo - Leibniz Research Centre for Working Environment and Human Factors, Dortmund |
| record_format | Article |
| series | EXCLI Journal : Experimental and Clinical Sciences |
| spelling | doaj.art-fb2bcd3013e24b0f8c93755fefd544c12023-04-20T13:27:01ZengIfADo - Leibniz Research Centre for Working Environment and Human Factors, DortmundEXCLI Journal : Experimental and Clinical Sciences1611-21562022-02-012136037910.17179/excli2021-45904029Synthesis of acetamidosulfonamide derivatives with antioxidative and QSAR studiesApilak Worachartcheewan0https://orcid.org/0000-0003-3021-3632Somchai Pisutjaroenpong1Ratchanok Pingaew2https://orcid.org/0000-0003-4977-5854Supaluk Prachayasittikul3https://orcid.org/0000-0002-5395-396XSuphakit Siriwong4https://orcid.org/0000-0002-3977-3356Somsak Ruchirawat5https://orcid.org/0000-0001-5842-4330Virapong Prachayasittikul6https://orcid.org/0000-0001-7942-1083Department of Community Medical Technology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand, Phone: (662) 441-4376; Fax: (662) 441-4380; E-mail: apilak.woa@mahidol.ac.thLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, Bangkok 10210, ThailandDepartment of Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok 10110, ThailandCenter of Data Mining and Biomedical Informatics, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand; E-mail: supaluk@g.swu.ac.thDepartment of Community Medical Technology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, ThailandLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, Bangkok 10210, Thailand; Program in Chemical Science, Chulabhorn Graduate Institute, Bangkok 10210, Thailand; Center of Excellence on Environmental Health and Toxicology, Commission on Higher Education (CHE), Ministry of Education, ThailandDepartment of Clinical Microbiology and Applied Technology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, ThailandA series of sixteen acetamidosulfonamide derivatives (1-16) have been synthesized and investigated for their antioxidant (radical scavenging and superoxide dismutase (SOD)) and antimicrobial activities. Most compounds exhibited antioxidant activities in which compound 15 displayed the most potent radical scavenging and SOD activities. Quantitative structure-activity relationship (QSAR) has been studied using multiple linear regression. The constructed QSAR models displayed high correlation coefficient (Q2/Loo-CV= 0.9708 and 0.8753 for RSA and SOD activities, respectively), but low root mean square error (RMSELOO-CV = 0.5105 and 1.3571 for RSA and SOD activities, respectively). The structure-activity relationship showed that an ethylene group connected to pyridine ring provided significant antioxidant activities. The QSAR models give insight into the rational designed of eighty new sulfonamides with various electron donating and withdrawing groups. The top five new designed sulfonamides with nitro group are potential antioxidants to be further developed for medicinal applications.https://www.excli.de/index.php/excli/article/view/4590sulfonamidesantioxidantssuperoxide dismutaseqsarrational design |
| spellingShingle | Apilak Worachartcheewan Somchai Pisutjaroenpong Ratchanok Pingaew Supaluk Prachayasittikul Suphakit Siriwong Somsak Ruchirawat Virapong Prachayasittikul Synthesis of acetamidosulfonamide derivatives with antioxidative and QSAR studies EXCLI Journal : Experimental and Clinical Sciences sulfonamides antioxidants superoxide dismutase qsar rational design |
| title | Synthesis of acetamidosulfonamide derivatives with antioxidative and QSAR studies |
| title_full | Synthesis of acetamidosulfonamide derivatives with antioxidative and QSAR studies |
| title_fullStr | Synthesis of acetamidosulfonamide derivatives with antioxidative and QSAR studies |
| title_full_unstemmed | Synthesis of acetamidosulfonamide derivatives with antioxidative and QSAR studies |
| title_short | Synthesis of acetamidosulfonamide derivatives with antioxidative and QSAR studies |
| title_sort | synthesis of acetamidosulfonamide derivatives with antioxidative and qsar studies |
| topic | sulfonamides antioxidants superoxide dismutase qsar rational design |
| url | https://www.excli.de/index.php/excli/article/view/4590 |
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