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Article

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
Molecules 2017, 22(1), 55; https://doi.org/10.3390/molecules22010055
Received: 8 December 2016 / Revised: 21 December 2016 / Accepted: 28 December 2016 / Published: 30 December 2016
(This article belongs to the Collection Heterocyclic Compounds)
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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MDPI and ACS Style

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. https://doi.org/10.3390/molecules22010055

AMA Style

Mphahlele MJ, Khoza TA, Mabeta P. Novel 2,3-Dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones: Synthesis and Biological Evaluation. Molecules. 2017; 22(1):55. https://doi.org/10.3390/molecules22010055

Chicago/Turabian Style

Mphahlele, Malose J., Tebogo A. Khoza, and Peaceful Mabeta. 2017. "Novel 2,3-Dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones: Synthesis and Biological Evaluation" Molecules 22, no. 1: 55. https://doi.org/10.3390/molecules22010055

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