The synthesis and biological activity of Trypanothione mimics and a series of quinoline derivatives designed as potential antileishmanial chemotherapies is reported. The biosynthesis of trypanothione is a unique pathway for parasites such as Leishmania and trypanosomes. A structure-guided design of trypanothione mimics led to the identification of 4 target compounds. Compounds 93 and 94 were designed to mimic the left-hand side chain, while compounds 105 and 106 mimicked side chains of molecule 59. The selected side chain mimics have not been previously assessed for their potential as TryR inhibitors. The left-hand side chain mimics 93/94 were synthesised from thioamine 85 and bromopropylamine 89 in six steps and in an overall yield of 2.3%. Side chain mimics 105/106 were synthesised from cysteine methyl ester 103 in five steps and in an overall yield of 3.5%. Five mimics, 93, 94, 98, 105 and 106, were tested in vitro against Leishmania major, however none exhibited activity. Preliminary enzymatic assays of mimics 94 and 106 against Trypanothione synthase indicated a degree of activity for 94 (inhibition >45 [microns]). [...]