_____________________________________________________________________________________________________ *Corresponding author: E-mail: egbujormc@gmail.com; Journal of Pharmaceutical Research International 32(8): 51-61, 2020; Article no.JPRI.54690 ISSN: 2456-9119 (Past name: British Journal of Pharmaceutical Research, Past ISSN: 2231-2919, NLM ID: 101631759) Design, Synthesis, Antimicrobial and Antioxidant Activities of Novel Threonine-based Sulfonamide Derivatives M. C. Egbujor 1* , U. C. Okoro 2 , D. C. Nwobodo 3 , C. U. Ezeagu 4 , U. B. Amadi 5 , C. G. Okenwa-Ani 1 , J. I. Ugwu 4 , I. G. Okoye 4 , I. P. Abu 3 and P. I. Egwuatu 3 1 Department of Industrial Chemistry, Renaissance University, Ugbawka, Enugu, Nigeria. 2 Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria. 3 Department of Microbiology, Renaissance University, Ugbawka, Enugu State, Nigeria. 4 Department of Biochemistry, Renaissance University, Ugbawka, Enugu State, Nigeria. 5 Chemistry Unit, Akanu Ibiam Federal Polytechnic Unwana, Ebonyi State, Nigeria. Authors’ contributions This work was carried out in collaboration among all authors. All authors read and approved the final manuscript. Article Information DOI:10.9734/JPRI/2020/v32i830470 Editor(s): (1) Dr. Vasudevan Mani, College of Pharmacy, Qassim University, Buraidah, Kingdom of Saudi Arabia. Reviewers: (1) Eman Fadlalla, Ain Shams University, Egypt. (2) M. E. Makgatho, University of Limpopo, South Africa. Complete Peer review History: http://www.sdiarticle4.com/review-history/54690 Received 10 December 2019 Accepted 14 February 2020 Published 30 May 2020 ABSTRACT Aim: To systematically design, synthesize and evaluate the biological activities of new threonine- based sulfonamide derivatives in order to achieve improved drug potency. Methodology: Sulfamoyl carboxylic acids were prepared by the reaction of threonine with the appropriate sulfonyl chloride while their acetylated, carboxamide and aniline derivatives were synthesized via Lumiere-Barbier acetylation, Schotten-Baumann ammonolysis and Buchwald- Hartwig cross-coupling methods respectively. The FTIR, 1 H-NMR, 13 C-NMR and elemental analytical data were employed in the structural characterization. In vitro and in silico antioxidant and antimicrobial studies were carried out. Results: Compounds 1b and 1d displayed the best in vitro antibacterial activities against Escherichia coli, Salmonella typhi, Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and antifungal activities against Candida albican sand Aspergillus niger. Compound 1f Original Research Article