Synthesis, Characterization, Biological Activity and Molecular Modeling Studies of Novel Aminoguanidine Derivatives

Abstract

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.

Design, synthesis, molecular docking and biological evaluation of 1,2,4-triazole derivatives possessing a hydrazone moiety as anti-breast cancer agents

“…The probable reaction mechanism is shown in Scheme 2. The structure of the synthesized compounds was confirmed by 1 H NMR, 13 C NMR, HRMS and FTIR spectroscopy and the structure of BIH2 was confirmed by single-crystal X-ray analysis. 1 H NMR, 13 C NMR, HRMS and FTIR data of the synthesized compounds are provided as ESI.…”

“…The structure of the synthesized compounds was confirmed by 1 H NMR, 13 C NMR, HRMS and FTIR spectroscopy and the structure of BIH2 was confirmed by single-crystal X-ray analysis. 1 H NMR, 13 C NMR, HRMS and FTIR data of the synthesized compounds are provided as ESI. † FTIR analysis of the target compounds exhibited the NH stretching bands around 3274 to 3321 cm À1 .…”

“…When varying the iodine concentration, it was noted that high yields were obtained in lower iodine concentrations. Further to improve the yield, the base molar ratio was tested at 10 mol%, 20 mol% and 30 mol% under the above-mentioned reaction conditions and the best maximum yield was obtained in 30 mol% of the base (Table 1, entries (10)(11)(12)(13)). In addition to this, we also investigated the effect of temperature on the above-mentioned reaction using different temperatures, for example, room temperature, 50 and 100 1C (Table 1, entries (14-16)).…”

“…Furthermore, a singlet corresponding to a methyl group was screened around d 2.21-2.29. 13 C NMR spectra of 2.2 Cytotoxic activity 2.2.1 Effect of the novel compounds on the viability of triple-negative breast cancer cells. The anticancer activity of the synthesized compounds was tested on MDA-MB-231 breast cancer cells.…”

“…However, compounds containing a hydrazone moiety have been reported to demonstrate significant biological activities as anti-breast cancer agents (Fig. 2), [11][12][13] in addition to activities against other diseases such as bacterial and fungal infections. [14][15][16][17] The bioactivity of compounds containing a hydrazone moiety is conjectured from its ability to form hydrogen bonds with molecular targets, making the compounds with this scaffold easily bind to numerous receptors and enzymes.…”