Synthesis of acetamidosulfonamide derivatives with antioxidative and QSAR studies

Authors

  • Apilak Worachartcheewan Department 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.th https://orcid.org/0000-0003-3021-3632
  • Somchai Pisutjaroenpong Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Bangkok 10210, Thailand
  • Ratchanok Pingaew Department of Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok 10110, Thailand https://orcid.org/0000-0003-4977-5854
  • Supaluk Prachayasittikul Center of Data Mining and Biomedical Informatics, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand; E-mail: supaluk@g.swu.ac.th https://orcid.org/0000-0002-5395-396X
  • Suphakit Siriwong Department of Community Medical Technology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand https://orcid.org/0000-0002-3977-3356
  • Somsak Ruchirawat Laboratory 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, Thailand https://orcid.org/0000-0001-5842-4330
  • Virapong Prachayasittikul Department of Clinical Microbiology and Applied Technology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand https://orcid.org/0000-0001-7942-1083

DOI:

https://doi.org/10.17179/excli2021-4590

Keywords:

sulfonamides, antioxidants, superoxide dismutase, QSAR, rational design

Abstract

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.

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Published

2022-02-01

How to Cite

Worachartcheewan, A., Pisutjaroenpong, S., Pingaew, R., Prachayasittikul, S., Siriwong, S., Ruchirawat, S., & Prachayasittikul, V. (2022). Synthesis of acetamidosulfonamide derivatives with antioxidative and QSAR studies. EXCLI Journal, 21, 360–379. https://doi.org/10.17179/excli2021-4590

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