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Tuberculosis (TB) and fungal diseases are opportunistic infections that very often complicate the immunological response in HIV-infected individuals [1-3]. During our studies on novel antimycobacterial and antifungal agents we synthesized a number of new pyrrole derivatives and among them some proved very active against both fungi and mycobacteria. Some others instead were very selective against mycobacteria only. So we pursued a program aimed at individuating the chemical groups or their association, responsible for the particular activity. Moreover, many other pyrroles we synthesized showed to be very active as COX-2 selective inhibitors. In this review we describe our approaches to the synthesis of the pyrrolic structures studied.