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In recent years, various compounds including the aminoguanidine scaffold have been reported to exhibit diverse biological activities. In the current study, 16 compounds that include guanylhydrazone (aminoguanidine) moiety (3 a-3 p) were synthesized and characterized through the spectrum data, including 1 H-NMR, 13 C-NMR, and FT-IR. Furthermore, the proposed structure of 3 a was resolved by single-crystal X-ray diffractometer. The prepared compounds were then tested for their different in vitro biological activities including antitumor activities against several types of cancer cell lines (A549, MCF-7, and U87-MG). Results showed that among the studied compounds especially 3 i, 3 n, and 3 p showed promising antiproliferative effect and they may be considered as good candidates for further in vitro and/or in vivo animal model studies. All the 16 derivatives synthesized in this study were also screened for their antimicrobial, antioxidant activity and DNA cleavage properties. Furthermore, multidimensional molecular modeling approaches were conducted for better understanding of their biological activities in atomic level.