Synthesis of a
chemical compound having the formula A-B-C that may serve for applications such as
drug delivery where A is a chemiluminescent,
moiety, B is a photochromic
moiety, and C is a biologically active
moiety where A-B-C may serve as a
prodrug. Novel synthetic methods of the present invention to form the
prodrug comprised the steps of (1) forming a
benzophenone, (2) forming a diaryl
ethylene, (3) attaching a
phthalimide moiety to at least one of the
aryl groups of the
ethylene to form a
phthalimide-
ethylene conjugate, (4) condensing two ethylene-
phthalimide conjugates to form a phthalimide-pentadiene conjugate, (5) converting the phthalimide to the phthalhydrazide by reaction with hydrazine to form a carrier compound according to the present invention, and (6) reacting the carrier compound with an nucleophilic moiety of the
drug to form the corresponding
prodrug. Alternatively the carrier can be prepared by using the halo-substituted diaryl ethylene to make the corresponding cationic
leuco dye-like compound with known methods. The cationic compound then is protected by reacting with a
nucleophile and coupled with the aminophathalimide by
palladium-catalyzed
amination to form the protected phthalimide-pentadiene conjugate. The latter is refluxed with hydrazine to convert its phthalimide to the phthalhydrazide and acidified to give the carrier. An additional aspect of the present invention relates to the use of these compounds as antiviral agents for the treatment of viral infections such as HIV and as anticancer agents for the treatment of cancers such as bowel,
lung, and
breast cancer.