ABSTRACT The specific objective of this research is to study the reaction of eugenol with formaldehyde and aniline and to perform in silico and biological activity studies on the obtained products. All the obtained structure compounds was confirmed by 1 H-NMR, 13 C-NMR, IR, MS and UV-Vis spectroscopic methods and then were tested for biological activity screening using in silico study by Molegro virtual Docker v 5.5 as a software. Docking process was used by Check point kinase 1 receptor (PDB ID: 2YWP) for screening biological anticancer activity. We have been using brine shrimp lethality test (BST) as in vitro study for anticancer activity screening The result of synthesis, compound (2):4-Allyl-2-methoxy-6-((phenylamino)-methyl)phenol, compound (3):6-Allyl-8-methoxy-3-phenyl-3,4-dihydro-2H-benzo-[e][1,3]oxazine and compound (4):6,6'-(Phenylazanediyl)bis(methylene)bis(4-allyl-2-methoxyphenol) were obtained by mannich reaction on eugenol using formaldehyde and aniline was stirred at room temperature for 0,5 h and reflux at 65 o C for 4 h with the yield product were 26 %, 52 % and 18 %. The results of docking process were benzoxazine and aminomethyl derivatives from eugenol have potential as anticancer activity based on their rerank score. The result of BST, It was found that all compounds have potential anticancer activity based on Meyer's criteria, therefore benzoxazine and aminomethyl derivatives have potential to be further studied for their bioactivity
