Synthesis and Biological Perspectives on Bay and Fjord Region Polycyclic Aromatic Hydrocarbons and Their Metabolites
Bhaskar Chatterjee, Smritilekha Bera, Dhananjoy MondalABSTRACT
Polycyclic aromatic hydrocarbons (PAHs) are pollutants formed by incomplete combustion, with bay‐ and fjord‐region PAHs being especially carcinogenic. Their metabolic activation by cytochrome P450 and epoxide hydrolase generates reactive diol epoxides that strongly bind to DNA and initiate tumor formation. Continuous synthetic advancement, including metal‐catalyzed couplings, oxidative photocyclization, acid catalyzed cyclization, Heck and Diels–Alder reactions, has enabled access to structurally PAH metabolites and modified amino triols, nucleoside adducts, hydroxylated, and aza‐ or thia‐derivatives for structure–activity studies. This review article highlights recent advances in the synthesis of PAH metabolites and analogues, and the structural factors for their biological effects.