Pyrrolo[1,2-a]quinazolines: synthesis and biological properties

Abstract

Pyrrolo[1,2-a]quinazolines have raised some interest as bioactive scaffolds but their synthetic strategies based mainly on the anthranilic acid route have been rather limited. The last two decades have brought new approaches to the synthesis of pyrrolo[1,2-a]quinazoline framework and thus their potential could be valued in the obtaining of new lead compounds from the important class of quinazolines. Herein we present the synthetic strategies towards compounds containing the pyrrolo[1,2-a]quinazoline scaffold and their biological properties.

The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones – an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones

“…In light of this, synthesis of compounds that are close analogs of natural compounds is an important task for the synthetic organic chemistry, and this approach has already provided successful results in the view of reaching biological activity. Thus, angular pyrrolo [1,2-a]quinazolines of type 1 -analogs of naturally occurring vasicinone alkaloids bearing an isomeric linear pyrrolo [2,1-b]quinazoline core [5][6][7][8] -demonstrated anti-inflammatory [9], antibacterial [10], antiarrythmic [11] activity; some representatives are CNS suppressors and poly-ADP ribose polymerase (PARP) inhibitors [12] (see Figure 1). Several approaches to obtain 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one derivatives of type 1 are known in the litera- ture to date.…”