Abstract
Amination of the 2-aryl-6-bromo-4-chloro-8-iodoquinazolines with 2-aminoethanol followed by acid-promoted cyclodehydration of the incipient 2-((6,8-dihalo-2-phenylquinazolin-4-yl)amino)ethanols afforded the corresponding novel 5-aryl-9-bromo-7-iodo-2,3-dihydro-2H-imidazo[1,2-c]quinazolines. The latter were, in turn, subjected to sequential (Sonogashira and Suzuki-Miyaura) and one-pot two-step (Sonogashira/Stille) cross-coupling reactions to afford diversely functionalized polycarbo-substituted 2H-imidazo[1,2-c]quinazolines. The imidazoquinazolines were screened for in vitro cytotoxicity against human breast adenocarcinoma (MCF-7) cells and human cervical cancer (HeLa) cells.
Highlights
Imidazo[1,2-c]quinazoline-based compounds continue to attract attention in synthesis because of their application in pharmaceuticals and materials [1]
A series of 5-alkyl substituted imidazo[1,2-c]quinazolines, for example, were screened for in vitro and in vivo bronchodilatory activity and the trend in activity was found to increase with increasing alkyl chain [2]
The SAR based on these preliminary in vitro cytotoxicity results revealed that the 9-(4-fluorophenyl) moiety on the heterocyclic framework is important for biological property of these polycarbo-substituted imidazoquinazolines
Summary
Imidazo[1,2-c]quinazoline-based compounds continue to attract attention in synthesis because of their application in pharmaceuticals and materials [1]. A series of 5-alkyl substituted imidazo[1,2-c]quinazolines, for example, were screened for in vitro and in vivo bronchodilatory activity and the trend in activity was found to increase with increasing alkyl chain (methyl < ethyl < propyl) [2]. Polycarbo-substituted 2,3-dihydro-2H-imidazo[1,2-c]quinazoline 1a [3,4] (Figure 1) and its 10-phenyl-8-trifluoromethyl isomer 1b [4] have been found to exhibit anti-inflammatory activity and to bind to cyclooxygenase isoenzyme (COX-1 and COX-2) of rat paw edema. The 5-(4-chlorostyryl)-2-phenylimidazo[1,2-c] quinazoline 2, on the other hand, was found to exhibit significant anti-cancer activity against HEP-G2 liver cell line [5]. The iridium and platinum cyclometalated imidazo[1,2-c]quinazolines have been patented as efficient dopants for organic electroluminescent layers in organic light emitting diodes (OLEDS) [6]
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