Abstract
A convenient three-step strategy is proposed for the synthesis of mono and bis-indolo[1,2-c] quinazolines from 2-(2-aminophenyl)indole and various aryl aldehydes. The newly synthesized compounds were characterized by elemental analysis, IR, ¹H NMR, 13C NMR, and mass spectroscopic investigation. All the derivatives were screened for antibacterial (S. aureus, B. subtilis, S. pyogenes, S. typhimurium, E. coli, K. pneumonia) and antifungal (A. niger, C. albicans, T. viridae) activities by cup plate method. Among the compounds tested, mono- indolo[1,2-c] quinazolines (15-18) exhibited good antibacterial activities while 15 and 18 also showed notable antifungal activity. Especially, 19 and 20 exhibited stronger antibacterial as well as antifungal activity against all tested strains.
Highlights
The indole is a crucial heterocyclic skeleton often associated with pharmacological properties.1,2 It is a fundamental constituent of a number of natural and synthetic products with biological activity.3,4 Due to the structural similarity of indole nuclei with some naturally occurring compounds such as serotonin, tryptamine, hinckdentine A, they can interact with biomolecules of the living systems.5,6 Heterocycles bearing an indole moiety are reported to show a broad spectrum of pharmacological and medicinal properties such as anti-inflammatory,7,8 anticonvulsant,9 antimicrobial,10,11 antimalarial,12,13 anticancer14,15 and many other activities.The introduction of an additional substituent on the indole nuclei has been increasing attention in the expectation that such changes could potentially affect the interaction of the molecules with biological targets
The indolo[1,2-c]quinazoline ring system was first prepared in 1956 by Kiang et al.,26 and Cava and Billimoria27 have reviewed the chemistry of indoloquinazolines, which are uncommon in nature
They have published an interesting approach to the synthesis of hinckdentine A and other indolo[1,2-c]quinazoline derivatives
Summary
The indole is a crucial heterocyclic skeleton often associated with pharmacological properties.1,2 It is a fundamental constituent of a number of natural and synthetic products with biological activity.3,4 Due to the structural similarity of indole nuclei with some naturally occurring compounds such as serotonin, tryptamine, hinckdentine A, they can interact with biomolecules of the living systems.5,6 Heterocycles bearing an indole moiety are reported to show a broad spectrum of pharmacological and medicinal properties such as anti-inflammatory,7,8 anticonvulsant,9 antimicrobial,10,11 antimalarial,12,13 anticancer14,15 and many other activities.The introduction of an additional substituent on the indole nuclei has been increasing attention in the expectation that such changes could potentially affect the interaction of the molecules with biological targets. Synthesis of Some New Mono, Bis-Indolo[1, 2-c]quinazolines
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