Synthesis and Cytotoxic Activity of Hexahydro-l,3,5-triazine Derivatives through Ring Condensation

摘要

As a part of a research program for pharmacologically interacting sym-triazine derivatives with hexahydrotriazine ring, novel hexahydrotriazine derivatives (1-13) were successfully synthesized. The synthesis of hexahydrotriazines was carried out from the assembly of three molecules of various amines and three molecules of formaldehyde by "1 + 1 + 1 + 1 + 1 + 1" cycloaddition. The synthesis mechanism is probably passes through imines, which trimerizes to give the hexahydrotriazine ring. All synthesized hexahydrotriazines (1-13) were screened for their cytotoxic activity by cancer cells. As a result, compound 1-9 reduced the viability of T98G cells in a concentration-dependent manner. At a concentration of 100 uM, compound 9 exhibited the greatest cytotoxicity at 94.6%. The reason is that compound 9 is C5H5N that has a resonance hybrid structure and exhibits aromaticity. It is considered to be active because it has a structure that is a raw material for pyridine derivatives as mainly medicines and pesticides.