Novel Polycarbo-Substituted Alkyl (Thieno[3,2-c]quinoline)-2-Carboxylates: Synthesis and Cytotoxicity Studies
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...
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doaj-97d52aded961425ca1e8c440e732adde2020-11-24T22:25:08ZengMDPI AGMolecules1420-30492014-11-011911185271854210.3390/molecules191118527molecules191118527Novel Polycarbo-Substituted Alkyl (Thieno[3,2-c]quinoline)-2-Carboxylates: Synthesis and Cytotoxicity StudiesMalose Jack Mphahlele0Marole Maria Maluleka1Tshepiso Jan Makhafola2Peace Mabeta3Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South AfricaDepartment of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South AfricaDepartment of Life and Consumer Sciences, College of Agriculture and Environmental Sciences, University of South Africa, Private Bag X06, Florida 1710, South AfricaDepartment of Anatomy and Physiology, University of Pretoria, P/Bag X04, Pretoria 0110, South AfricaDirect 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. http://www.mdpi.com/1420-3049/19/11/185276,8-dibromo-4-chloroquinoline-3-carbaldehydeSuzuki-Miyaura cross-couplingalkyl thieno[3,2-c]quinoline-2-carboxylatesMCF-7 cell linecytotoxicity |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Malose Jack Mphahlele Marole Maria Maluleka Tshepiso Jan Makhafola Peace Mabeta |
spellingShingle |
Malose Jack Mphahlele Marole Maria Maluleka Tshepiso Jan Makhafola Peace Mabeta Novel Polycarbo-Substituted Alkyl (Thieno[3,2-c]quinoline)-2-Carboxylates: Synthesis and Cytotoxicity Studies Molecules 6,8-dibromo-4-chloroquinoline-3-carbaldehyde Suzuki-Miyaura cross-coupling alkyl thieno[3,2-c]quinoline-2-carboxylates MCF-7 cell line cytotoxicity |
author_facet |
Malose Jack Mphahlele Marole Maria Maluleka Tshepiso Jan Makhafola Peace Mabeta |
author_sort |
Malose Jack Mphahlele |
title |
Novel Polycarbo-Substituted Alkyl (Thieno[3,2-c]quinoline)-2-Carboxylates: Synthesis and Cytotoxicity Studies |
title_short |
Novel Polycarbo-Substituted Alkyl (Thieno[3,2-c]quinoline)-2-Carboxylates: Synthesis and Cytotoxicity Studies |
title_full |
Novel Polycarbo-Substituted Alkyl (Thieno[3,2-c]quinoline)-2-Carboxylates: Synthesis and Cytotoxicity Studies |
title_fullStr |
Novel Polycarbo-Substituted Alkyl (Thieno[3,2-c]quinoline)-2-Carboxylates: Synthesis and Cytotoxicity Studies |
title_full_unstemmed |
Novel Polycarbo-Substituted Alkyl (Thieno[3,2-c]quinoline)-2-Carboxylates: Synthesis and Cytotoxicity Studies |
title_sort |
novel polycarbo-substituted alkyl (thieno[3,2-c]quinoline)-2-carboxylates: synthesis and cytotoxicity studies |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2014-11-01 |
description |
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. |
topic |
6,8-dibromo-4-chloroquinoline-3-carbaldehyde Suzuki-Miyaura cross-coupling alkyl thieno[3,2-c]quinoline-2-carboxylates MCF-7 cell line cytotoxicity |
url |
http://www.mdpi.com/1420-3049/19/11/18527 |
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