Photochemistry of flutamide in various media: Investigation of the reaction mechanism as revealed by external magnetic field effects on product yields

Photochemistry of an anticancer drug flutamide, 2-methyl-N-[4-nitro-3-(trifluoromethyl) phenyl] propanamide has been investigated in various media in the absence and presence of 0.1 T magnetic field. On photoexcitation flutamide gives rise to a phenol derivative through nitro-to-nitrite rearrangement in homogeneous as well as in inhomogeneous solutions. Magnetic field effects on the product yields revealed that a radical pair is involved in the photoreduction, where the excited triplet state of flutamide is the precursor of the pair. It undergoes hydrogen abstraction reaction in inhomogeneous solutions where solvent molecules act not only as component of solvent cage but also as hydrogen donor.

► The influence of various media was investigated on photochemistry of flutamide.
► Photoproducts of flutamide, Product 1 and Product 2, were unambiguously identified in comparison with authentic samples.
► Analysis of magnetic field effects on photoreactions of flutamide in various media reveals the detailed reaction mechanism.