Recent developments in the chemistry of quinazolinone alkaloids

Abstract

Quinazolinones, an important class of fused heterocyclic alkaloids has attracted high attention in organic and medicinal chemistry due to their significant and wide range of biological activities. There are approximately 150 naturally occurring quinazolinone alkaloids known till 2005. Several new quinazolinone alkaloids (∼55) have been isolated in the last decade. Natural quinazolinones with exotic structural features and remarkable biological activities have incited a lot of activities in the synthetic community towards the development of new synthetic strategies and approaches for the total synthesis of quinazolinone alkaloids. This review is focused on these advances in the chemistry of quinazolinone alkaloids in the last decade. This article covers the newly isolated quinazolinone natural products with their biological activities and the recently reported total syntheses of quinazolinone alkaloids from 2006 to 2015.

Biologically active quinoline and quinazoline alkaloids part I

“…Quinazoline alkaloids are another class of N ‐based heterocyclic compounds. To date, approximately 150 naturally occurring quinazoline alkaloids have been isolated from several families of the plant kingdom, as well as from animals and microorganisms; many are derived biogenetically from anthranilic acid . In 1888, the first quinazoline alkaloid, vasicine ( 3 ) (Fig.…”

Hydrogen Atom Transfer‐Mediated Domino Cyclisation Reaction to Access (Spiro)Quinazolinones

“…This method, using PhSiH 3 and catalytic Fe(acac) 3 ,a llows for the synthesis of challenging (spiro)quinazolinone scaffolds from simple, tractable (hetero)aryl carboxylic acid and cyanamide building blocks.Quinazolinones are an important class of nitrogen-containing heterocycles and the scaffold has been labelleda sa'privileged structure' within medicinal chemistry. [1] Approximately 200 naturally occurring quinazolinonea lkaloids have been isolated [2] and they show aw ide range of biological properties such as analgesic, anti-bacterial, anti-fungal, anti-convulsant, anti-inflammatory,a nti-HIV and anti-cancer activities. [3] For example, diproqualone (Scheme 1) is in widespreadc linicalu se fori ts anti-inflammatory,analgesic and sedative effects.Commonly,m ethods to synthesise these importantc ores start from o-aminobenzamideso ro-aminobenzoic acids, an example being the classical Niementowski quinazolinone synthesis (Scheme 2a(i)).…”

Total Synthesis of Fontanesine B and Its Isomer: Their Antiproliferative Activity against Human Colorectal Cancer Cells

“…Fontanesines belong to a rare pyrano [3,2-e]indoloquinazoline alkaloid. Although pyranoindole and pyranocarbazole alkaloids have been extensively synthesized, [2][3][4] pyrano [3,2-e]indoloquinazoline alkaloids were not reported. These and the unprecedented carbon skeleton of 2 prompted us to undertake its synthesis.…”