| Diaryl sulfones have been found to have significant anti-Human Immunodeficiency Virus (HIV) activity as non-nucleoside reverse-transcriptase inhibitors (NNRTIs). NNRTI compounds are among the most effective anti-HIV agents known. Unfortunately, resistance or cross-resistance of the virus frequently occurs compromising the effects of existing drugs. Our focus is the synthesis of a new series of diaryl sulfones to combat the rapidly emerging mutant strains of HIV. N-Alkyl arylsulfonanilides and cyclic aryl aminesulfonanilides have been shown to rearrange to diaryl sulfones in the presence of concentrated sulfuric acid, strong bases or heat. Previously, in this laboratory, this technology has been extended to heterocyclic sulfonanilides where the amine is incorporated into a benzo-fused five, six or seven membered heterocyclic ring. In hopes of further expanding the scope of this reaction, the project to prepare sulfonamides of benzodiazepines was undertaken to ascertain whether they too will undergo this type of rearrangement when a second nitrogen is present in the heterocycle. Rearranged compounds will be evaluated for their anti-HIV activity. A new series of potentially useful benzodiazepine sulfonamides will be generated in the process. |
