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Several novel 6-aryl-5-cyano thiouracil derivatives were synthesized and explored for their activities as antibacterial, antifungal and anticancer agents. The antimicrobial evaluation revealed that compounds <strong>7b</strong> and <strong>7c</strong> possessed superior antibacterial activity against the Gram positive bacteria <em>S. aureus</em> and <em>B. subtilis</em> compared to the reference drug amoxicillin. Moreover, compound <strong>4i</strong> was found to be a broad spectrum antimicrobial agent and it also exhibited the highest antifungal activity against <em>C. albicans</em>, even higher than the reference drug amphotericin B (MIC = 2.34, 3.00 μg/mL respectively). Selected compounds were tested for <em>in vitro</em> cytotoxicity at a single 10<sup>−5</sup> M concentration in accordance to the NCI (USA) protocol. The preliminary screening results showed that most of the compounds had limited cytotoxic activity against renal cancer UO-31 and/or A498 cell lines. Nevertheless, compounds <strong>6d</strong> and <strong>6i</strong> displayed potent growth inhibitory effect toward non-small cell lung cancer HOP-92 and leukemia MOLT-4 cell lines, respectively.