<i>Chlamydia trachomatis</i> is the most common sexually transmitted bacterial disease globally and the leading cause of infertility and preventable infectious blindness (trachoma) in the world. Unfortunately, there is no FDA-approved treatment specific for chlamydial infections. We recently reported two sulfonylpyridines that halt the growth of the pathogen. Herein, we present a SAR of the sulfonylpyridine molecule by introducing substituents on the aromatic regions. Biological evaluation studies showed that several analogues can impair the growth of <i>C. trachomatis</i> without affecting host cell viability. The compounds did not kill other bacteria, indicating selectivity for <i>Chlamydia</i>. The compounds presented mild toxicity toward mammalian cell lines. The compounds were found to be nonmutagenic in a <i>Drosophila melanogaster</i> assay and exhibited a promising stability in both plasma and gastric fluid. The presented results indicate this scaffold is a promising starting point for the development of selective antichlamydial drugs.