The major challenges of Mycobacterium tuberculosis treatment are the emergence of multidrug resistant or extensively drug resistant strains and the hepatotoxic adverse drug reactions of current antitubercular drugs. With an incidence of approximately 9.4 million people, tuberculosis is one of the leading causes of death by an infectious agent. 2-Decylsulfonylacetamide represents a novel class of compounds shown to have comparable antitubercular activity to the first-line antitubercular drugs isoniazid and rifampicin. The aim of this research was to synthesize a library of 2-decylsulfonylacetamide derivatives, substituting the acetamide moeity with a variety of functional groups (methyl ester, carboxylic acid, thioamide and an alkyne); elucidate and characterise synthesised compounds using Nuclear Magnetic Resonance, Mass Spectrometry, Attenuated Total Reflectance Fourier Transform Infrared Red Spectroscopy, Differential Thermal Analysis; determine their in vitro antitubercular activity; evaluate and compare their in vitro antibacterial (Staphyloccocus aureus, Escherichia coli, Pseudomonas aeruginosa) and antifungal (Candida albicans) activities; evaluate and compare in vitro cytotoxicity profiles using A549 (adenocarcinomic human alveolar basal epithelial cells), HeLa (cervical adenocarcinoma), Jurkat (acute T cell leukemia), LNCap (prostate carcinoma) and MCF-7 (human breast adenocarcinoma) cell lines; evaluate the in vitro hepatotoxicity potential of synthesised compounds to select current antitubercular agents; and assess the immunomodulating effects (in A549 and Jurkat cells) of the synthesised 2-decylsulfonylacetamide and its derivatives using the A549 and Jurkat in vitro models in an attempt to characterise their potential effects on the non-specific and specific immune system.