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Molecules 2015, 20(7), 12412-12435; doi:10.3390/molecules200712412

Synthetic Development of New 3-(4-Arylmethylamino)butyl-5-arylidene-rhodanines under Microwave Irradiation and Their Effects on Tumor Cell Lines and against Protein Kinases

1
Université de Rennes 1, Institut des Sciences Chimiques de Rennes (ISCR), UMR CNRS 6226, Groupe ICMV, Bât. 10A, Campus de Beaulieu, 263 Avenue du Général Leclerc, CS 74205, 35042 Rennes Cedex, France
2
Laboratoire de Chimie Bio-Organique et de Substances Naturelles (LCBOSN), Université Nangui Abrogoua, Abidjan 02, BP 802, Cote d'Ivoire
3
UFR des Sciences Biologiques, Université de Péléforo Gon Coulibaly, Korhogo, BP 1328, Cote d'Ivoire
4
Station Biologique de Roscoff, USR 3151, CNRS-UPMC, Kinase Inhibitory Specialized Screening facility, KISSf, Place George Teissier, BP 74, 29682 Roscoff, France
5
Université de Rennes 1, ImPACcell, SFR Biosit, Bât. 8, 2 Avenue du Professeur Léon Bernard, CS 34317, 35043 Rennes Cedex, France
*
Author to whom correspondence should be addressed.
Academic Editor: Marilena Radoiu
Received: 27 May 2015 / Revised: 17 June 2015 / Accepted: 30 June 2015 / Published: 8 July 2015
(This article belongs to the Special Issue Microwave-Assisted Organic Synthesis)
View Full-Text   |   Download PDF [847 KB, uploaded 8 July 2015]   |  

Abstract

A new route to 3-(4-arylmethylamino)butyl-5-arylidene-2-thioxo-1,3-thiazolidine-4-one 9 was developed in six steps from commercial 1,4-diaminobutane 1 as starting material. The key step of this multi-step synthesis involved a solution phase “one-pot two-steps” approach assisted by microwave dielectric from N-(arylmethyl)butane-1,4-diamine hydrochloride 6af (as source of the first point diversity) and commercial bis-(carboxymethyl)-trithiocarbonate reagent 7 for construction of the rhodanine platform. This platform was immediately functionalized by Knoevenagel condensation under microwave irradiation with a series of aromatic aldehydes 3 as second point of diversity. These new compounds were prepared in moderate to good yields and the fourteen synthetic products 9an have been obtained with a Z-geometry about their exocyclic double bond. These new 5-arylidene rhodanines derivatives 9an were tested for their kinase inhibitory potencies against four protein kinases: Human cyclin-dependent kinase 5-p25, HsCDK5-p25; porcine Glycogen Synthase Kinase-3, GSK-3α/β; porcine Casein Kinase 1, SsCK1 and human HsHaspin. They have also been evaluated for their in vitro inhibition of cell proliferation (HuH7 D12, Caco 2, MDA-MB 231, HCT 116, PC3, NCI-H727, HaCat and fibroblasts). Among of all these compounds, 9j presented selective micromolar inhibition activity on SsCK1 and 9i exhibited antitumor activities in the HuH7 D12, MDA-MBD231 cell lines. View Full-Text
Keywords: one-pot two-steps; Knoevenagel condensation; 5-arylidene rhodanine; protein kinase; inhibitor; SsCK1; HsCDK5-p25; cell lines; Alzheimer’s disease; cancer one-pot two-steps; Knoevenagel condensation; 5-arylidene rhodanine; protein kinase; inhibitor; SsCK1; HsCDK5-p25; cell lines; Alzheimer’s disease; cancer
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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

Dago, C.D.; Ambeu, C.N.; Coulibaly, W.-K.; Békro, Y.-A.; Mamyrbékova, J.; Defontaine, A.; Baratte, B.; Bach, S.; Ruchaud, S.; Guével, R.L.; Ravache, M.; Corlu, A.; Bazureau, J.-P. Synthetic Development of New 3-(4-Arylmethylamino)butyl-5-arylidene-rhodanines under Microwave Irradiation and Their Effects on Tumor Cell Lines and against Protein Kinases. Molecules 2015, 20, 12412-12435.

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