Tricyclic Quinazoline Alkaloids: Isolation, Synthesis, Chemical Modification, and Biological Activity

Abstract

Results of the last 15-20 years on the isolation, synthesis, chemical modification, and biological activity of natural tricyclic quinazolines and their synthetic analogs were reviewed.

Progress in Studies on Rutaecarpine. II.—Synthesis and Structure-Biological Activity Relationships

“…Of the 17 review papers written to date, eight have focused on the synthesis of rutaecarpine [7,8,9,10,11,12,13,14], seven on pharmacology [15,16,17,18,19,20,21], one on the modulation of cytochrome P450 [22], and one on detection methods [23]. A review published in 1983 by Bergman [7] covers the nomenclature, structure, synthesis and pharmacological properties of rutaecarpine and of related quinazolinone alkaloids.…”

An expedient synthesis of oxazepino and oxazocino quinazolines

“…The selection of amino alcohol would probe the parameters of the Niementowski (2) and BOP (3) mediated ring closures ( Table 3). The previously reported 23 SNAr reaction of 6-fluoro-2-aminobenzonitrile with a limited selection of aminoalcohols generally proceeded in modest to good yields (Table 1).…”

“…Quinazolines belong to a privileged class of bioactive small molecules, 1 which are found in a collection of natural products 2 and interact with a variety of important biological targets 3 including tankyrase-1 protein 4 (as a senescence inducer), aswell as various anticonvulsant 5 and antifungal targets. 6 Most notably, several substituted quinazolines act as anti-cancer ATP-competitive kinase inhibitors.…”

Stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate

“…Tricyclic quinazoline alkaloids are frequently encountered in nature (Michael, 1997;Eguchi, 2006;Shakhidoyatov et al, 2014). The reason for the wide interest in studying these substances lies in their multi-facetted biological activity: they have been associated with antibacterial (Jantova et al, 2004), tumor growth-inhibiting (Aoyagi et al, 1999;Kuneš et al, 2000;Foster et al, 1999;Forsch et al, 2002;Abdel-Jalil et al, 2005), Chemical scheme showing the synthesis of the title compound antifungal (Dandia et al, 2005;Nikhil et al, 2011), antihyperglycemic (Ram et al, 2003) and anti-inflammatory (Yeh-Long et al, 2004) activity.…”