Survey of Recent Literature Related to the Biologically Active 4(3H)-Quinazolinones Containing Fused Heterocycles

Abstract

The present review focuses on the synthesis and biological evaluation of polycyclic 4(3H)-quinazolinones containing fused aromatic or heteroaromatic rings. The first part of the review is related to compounds with ring fused to the pyrimidine part of the quinazoline core. Most of the quinazolinone alkaloids belong to this class of molecules. The second part presents molecules bearing extra ring(s) fused to the benzo moiety of the quinazolinone skeleton. Their structural diversity opens new fields in the search of active molecules.

Antitumor Activity of Quinazolinone Alkaloids Inspired by Marine Natural Products

“…Marine alkaloids containing indolymethyl pyrazinoquinazoline ring system can be considered conformationally constrained peptidomimetics exhibiting very interesting biological properties [15]. For instance, glyantrypine ( 2 ) is an antibacterial agent, active against Vibrio harveyi [16]; fumiquinazolines are antitumor compounds with moderate cytotoxicity [17]; fiscalins are substance P inhibitors and anticancer agents [7,18]; cladoquinazolines ( 9 and 10 ) are active against influenza A virus (H 1 N 1 ); fumiquinazoline S ( 12 ) exhibits a weak inhibition against Na + /K + -ATPase, and N -acetylardeemin ( 14 ) is a potent inhibitor of multidrug resistant (MDR) tumor cells [4,13,19,20].…”

Iodine Catalyzed Oxidative Synthesis of Quinazolin-4(3H)-ones and Pyrazolo[4,3-d]pyrimidin-7(6H)-ones via Amination of sp3 C–H Bond

“…quinazolin-4(3H)-ones, pyrazolo [4,3-d]pyrimidin-7(6H)-ones, sp 3 C-H bond functionalization, molecular iodine, oxidative coupling Quinazolin-4(3H)-ones are an important class of fused heterocycles having wide occurrence among natural products [1][2][3][4][5][6] and bioactive compounds. 7,8 Especially, 2-aryl substituted quinazolinones have been reported as potent kinase inhibitors (e.g. idelalisib).…”

Palladium‐Catalyzed Synthesis of Phenanthridine/Benzoxazine‐Fused Quinazolinones by Intramolecular CH Bond Activation

“…Recently, heteroaromatic ring‐fused 4(3 H )‐quinazolinones and halogenated quinazolinones/quinazolines have been reported as versatile synthetic intermediates to generate novel biologically relevant poly‐substituted derivatives 13. 14 In addition, quinazolinone derivatives are also used as inhibitors of various enzymes, including monoamine oxidase, aldose reductase, tumor necrosis factor R, and thymidylate synthases 15. Phenanthridine structural motifs represent another class of biologically relevant compounds with extensive pharmacological activities and applications 16.…”