Antimicrobial resistance is one of the world’s greatest health challenges. In 2015, WHO reported that at least 700,000 people died from antimicrobial resistance. One of the natural compounds found in Indonesia and reported to have antimicrobial activity is eugenol. However, the activity of the resulting compound is still very weak, so it is necessary to modify the functional group to increase its antimicrobial activity by adding an amine group. In this study, the synthesis of Aminoalkylated eugenol compounds with the addition of morpholine (compound 1) and dimethylamine (compound 2) groups was carried out based on In Vitro and In Silico studies. In Silico method using Discovery Studio software on sensitive Staphylococcus aureus bacteria with protein code 3VOB.pdb. and resistant Staphylococcus aureus bacteria with protein code 2X3F.pdb. In addition, antibacterial activity was also tested against sensitive Eschericia coli bacteria with the protein code 2JOW.pdb. and resistant Eschericia coli bacteria with protein code 7C7O.pdb. To understand the interactions formed by the structure of the compounds confirmed by spectrophotometric analysis using MS, 1H-NMR and 13C-NMR. Eugenol without the addition of an amine group in S. aureus showed a zone of 12.2 mm and the addition of morpholine and dimethylamine significantly increased the antibacterial activity to 15.2 mm and 18.6 mm, respectively, while eugenol without the addition of an amine group in E. coli bacteria. showed a zone of 11.5 mm and the addition of morpholine and dimethylamine could significantly increase the antibacterial activity to 14.3 mm and 20 mm, respectively. The molecular docking of these compounds showed strong hydrogen bond interactions with SER186, ARG188, ASP151, HIS35, LYS150, LYS185, PHE147, with CDOCKER interaction energy of-48.84 kcal/mol.

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