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Molecules 2014, 19(11), 18527-18542; doi:10.3390/molecules191118527

Novel Polycarbo-Substituted Alkyl (Thieno[3,2-c]quinoline)-2-Carboxylates: Synthesis and Cytotoxicity Studies

1
Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa
2
Department of Life and Consumer Sciences, College of Agriculture and Environmental Sciences, University of South Africa, Private Bag X06, Florida 1710, South Africa
3
Department of Anatomy and Physiology, University of Pretoria, P/Bag X04, Pretoria 0110, South Africa
*
Author to whom correspondence should be addressed.
Received: 8 September 2014 / Revised: 6 November 2014 / Accepted: 7 November 2014 / Published: 13 November 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

Direct one-pot base-promoted conjugate addition–elimination of 6,8-dibromo-4-chloroquinoline-3-carbaldehyde with methyl mercaptoacetate and subsequent cyclization afforded methyl [(6,8-dibromothieno[3,2-c]quinoline)]-2-carboxylate. The latter undergoes Suzuki-Miyaura cross-coupling with arylboronic acids to yield exclusively the corresponding alkyl [(6,8-diarylthieno[3,2-c]quinoline)]-2-carboxylates,. The cytotoxicity of the prepared compounds was evaluated against the human breast cancer cell line MCF-7 using the MTT assay. The effects of compounds 2, 3c and 4d on cell kinetics were further determined using the xCELLigence Real Time Cell Analysis (RTCA) system. In both the MTT assay and Real Time Cell Analysis, the compounds inhibited cancer cell growth in a dose- and time-dependent manner. Furthermore, on the basis of the calculated LC50 values, the compounds compared favourably with nocodazole, a well-established anticancer drug. View Full-Text
Keywords: 6,8-dibromo-4-chloroquinoline-3-carbaldehyde; Suzuki-Miyaura cross-coupling; alkyl thieno[3,2-c]quinoline-2-carboxylates; MCF-7 cell line; cytotoxicity 6,8-dibromo-4-chloroquinoline-3-carbaldehyde; Suzuki-Miyaura cross-coupling; alkyl thieno[3,2-c]quinoline-2-carboxylates; MCF-7 cell line; cytotoxicity
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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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MDPI and ACS Style

Mphahlele, M.J.; Maluleka, M.M.; Makhafola, T.J.; Mabeta, P. Novel Polycarbo-Substituted Alkyl (Thieno[3,2-c]quinoline)-2-Carboxylates: Synthesis and Cytotoxicity Studies. Molecules 2014, 19, 18527-18542.

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