Synthesis and characterization of acetoguanamine crown ethers by microwave method

Crown ethers are frequently used for metal complexation due to their affinity for cations. Such compounds contain a hydrophobic outer cavity and a hydrophilic inner cavity. Crown ethers are named as oxo, aza, benzo, thio, etc. depending on the donor atoms and side groups they contain. Depending on the number, proportions and diversity of functional groups and donor atoms, they show interest in a wide range of different elemental ions. For this reason, the synthesis and characterization of compounds containing different heteroatom-containing groups on the side group have been targeted. In this study, crown ether derivatives of acetoguanamine (2,4-diamino-6-methyl-1,3,5-triazine), one of the triazine class heterocyclic compounds and intermediate of many pharmaceuticals, were synthesized by SN2 mechanism of 2,4-diamino-6-methyl-1,3,5-triazine and poly(ethylene) glycol dihalides. A basic catalyst (Cs2CO3) and microwave-assisted synthesis method were used in the reaction. Targeted acetoguanamine crown ether derivatives were synthesized using microwave-assisted synthesis method and green chemistry techniques. After purification of the synthesized macrocyclic 2,4-diamino-6-methyl-1,3,5-triazine crown ether derivatives, their structural characterization was carried out by FTIR, NMR and MS methods. The DPPH radical scavenging effect and DNA protection activity of these compounds were tested experimentally. Among the compounds, only S1 had a low radical scavenging effect (mean 5.2), and all compounds did not affect the applied DNA plasmid and did not show DNA protection effect. In addition, thanks to the heteroatoms they contain, they can be used for the removal of metal ions from liquid media.