Perylenequinone analogs

Scheme 7.22 Synthesis of C3,C3 -substituted C7,C7 -propyl perylenequinone analogs...

The development of new synthetic methodology has successfully enabled the investigation of structure-activity relationships (SAR) of perylenequinone agents for use in photodynamic therapy. Simplified analogs, such as (M)-96, that have potency equal to the natural product hypocrellin and superior chromophores to improve photoactivation in the therapeutic window were prepared. 

The architecturally interesting and biologically significant protein kinase C inhibitor calphostins (A-D), and their analogs were synthesized in the laboratory of C.A. Merlic. The key steps in their approach were a Dotz aminobenzannulation utilizing an enantiopure Fischer carbene complex to prepare a pentasubstituted naphthylamine, followed by a biomimetic oxidative dimerization to produce the perylenequinone skeleton. 

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