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Molecules 2017, 22(1), 55; doi:10.3390/molecules22010055

Novel 2,3-Dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones: Synthesis and Biological Evaluation

1
Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, Private Bag X06, Florida 1710, South Africa
2
Department of Anatomy and Physiology, University of Pretoria, P/Bag X04, Pretoria 0110, South Africa
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 8 December 2016 / Revised: 21 December 2016 / Accepted: 28 December 2016 / Published: 30 December 2016
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [1338 KB, uploaded 30 December 2016]   |  

Abstract

Herein we describe the synthesis and evaluation of a series of novel 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones for in vitro cytotoxicity against three human cancer cell lines as well as for potential antimalarial activity against the chloroquine-sensitive strain 3D7 of Plasmodium falciparum. The title compounds were prepared via PdCl2-mediated endo-dig cyclization of 2-aryl-8-(arylethynyl)-6-bromo-2,3-dihydroquinazolin-4(1H)-ones. The latter were prepared, in turn, via initial Sonogashira cross-coupling of 2-amino-5-bromo-3-iodobenzamide with aryl acetylenes followed by boric acid-mediated cyclocondensation of the intermediate 2-amino-3-(arylethynyl)-5-bromobenzamides with benzaldehyde derivatives. The 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones 4ak were evaluated for potential in vitro cytotoxicity against the breast (MCF-7), melanoma (B16) and endothelioma (sEnd.2) cell lines. All of the compounds except 4h and 4i were found to be inactive against the three cancer cell lines. Compound 4h substituted with a 4-methoxyphenyl and 4-fluorophenyl groups at the 3- and 5-positions was found to exhibit significant cytotoxicity against the three cancer cell lines. The presence of phenyl and 3-chlorophenyl groups at the 3- and 5-posiitons of the pyrroloquinazolinone 4i, on the other hand, resulted in significant cytotoxicity against vascular tumour endothelial cells (sEnd.2), but reduced activity against the melanoma (B16) and breast cancer (MCF-7) cells except at higher concentrations. The 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones 4al were found to be inactive against the chloroquine sensitive 3D7 strain of Plasmodium falciparum. View Full-Text
Keywords: 1H-pyrrolo[3,2,1-ij]quinazolin-1-ones; X-ray; cytotoxicity; Plasmodium falciparum; antiplasmodial activity 1H-pyrrolo[3,2,1-ij]quinazolin-1-ones; X-ray; cytotoxicity; Plasmodium falciparum; antiplasmodial activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Mphahlele, M.J.; Khoza, T.A.; Mabeta, P. Novel 2,3-Dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones: Synthesis and Biological Evaluation. Molecules 2017, 22, 55.

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