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DESIGN, SYNTHESIS, AND EVALUATION OF CARBAZOLE ANALOGS AS POTENTIAL CYTOCHROME P450 INHIBITORS.

Carbazoles are a class of nitrogen-containing aromatic heterocyclic compounds. They not only have various biological activities (e.g. antibacterial, anti-inflammatory, antitumor), but also exhibit useful properties as organic materials due to their special structures. Cytochrome P450 enzymes are a superfamily of hemoproteins involved in the metabolism of endogenous and exogenous compounds including many drugs and environmental chemicals. Some aryl and arylalkyl acetylenes, and propargyl ethers have been shown to act as inhibitors of certain P450s. In an attempt to improve the potency and selectivity of inhibition, we have focused our attention on the design and synthesis of a new series of carbazole analogs, a few of which contain a propargyl ether functional group. For this project, eight carbazole analogs have been synthesized and characterized.