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Keywords = 6,8-dibromo-4-chloroquinoline-3-carbaldehyde

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16 pages, 751 KB  
Article
Novel Polycarbo-Substituted Alkyl (Thieno[3,2-c]quinoline)-2-Carboxylates: Synthesis and Cytotoxicity Studies
by Malose Jack Mphahlele, Marole Maria Maluleka, Tshepiso Jan Makhafola and Peace Mabeta
Molecules 2014, 19(11), 18527-18542; https://doi.org/10.3390/molecules191118527 - 13 Nov 2014
Cited by 9 | Viewed by 6453
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 [...] Read more.
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. Full article
(This article belongs to the Section Organic Chemistry)
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19 pages, 515 KB  
Article
4,6,8-Triarylquinoline-3-carbaldehyde Derivatives: Synthesis and Photophysical Properties
by Malose Jack Mphahlele and Adewale Olufunsho Adeloye
Molecules 2013, 18(12), 15769-15787; https://doi.org/10.3390/molecules181215769 - 17 Dec 2013
Cited by 12 | Viewed by 6075
Abstract
Palladium catalyzed Suzuki-Miyaura cross-coupling of 6,8-dibromo-4-chloroquinoline-3-carbaldehyde with arylboronic and arylvinylboronic acid derivatives in the presence of potassium carbonate in aqueous dioxane afforded the corresponding 4,6,8-triarylquinoline-3-carbaldehydes, exclusively. These products were transformed into 4,6,8-triaryl-3-(4-fluorophenyl)amino)-N-(quinolin-3-yl)methylenes and their 4,6,8-triaryl-quinoline-3-methanol derivatives. The absorption and emission spectra [...] Read more.
Palladium catalyzed Suzuki-Miyaura cross-coupling of 6,8-dibromo-4-chloroquinoline-3-carbaldehyde with arylboronic and arylvinylboronic acid derivatives in the presence of potassium carbonate in aqueous dioxane afforded the corresponding 4,6,8-triarylquinoline-3-carbaldehydes, exclusively. These products were transformed into 4,6,8-triaryl-3-(4-fluorophenyl)amino)-N-(quinolin-3-yl)methylenes and their 4,6,8-triaryl-quinoline-3-methanol derivatives. The absorption and emission spectra were measured for the 4,6,8-triarylquinoline-3-carbaldehydes and their derivatives in selected solvents of different polarity. Full article
(This article belongs to the Section Organic Chemistry)
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