Microwaves in Heterocyclic Chemistry

Bazureau, Jean Pierre; Paquin, Ludovic; Carrié, Daniel; L'Helgoual'ch, Jean Martial; Guihéneuf, Solène; Coulibaly, Karime Wacothon; Burgy, Guillaume; Komaty, Sarah; Limanton, Emmanuelle

doi:10.1002/9783527651313.ch16

Cited by 9 publications

(3 citation statements)

References 158 publications

(143 reference statements)

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“…A detailed account of condensation reactions as applied to heterocyclic chemistry is given in Section 10.4 and in Chapter 16 [97], and for cycloaddition reactions in Chapter 17 [98]. …”

Section: Condensation Reactions 441mentioning

confidence: 99%

“…An exhaustive overview was provided in chapters in the previous edition [97,98], with limited solvent-free chemistry utilizing mineral supported reagents being covered in this section. An exhaustive overview was provided in chapters in the previous edition [97,98], with limited solvent-free chemistry utilizing mineral supported reagents being covered in this section.…”

Section: Synthesis Of Heterocyclic Compoundsmentioning

confidence: 99%

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Organic Synthesis Using Microwaves and Supported Reagents

Varma

Baig

2012

Microwaves in Organic Synthesis

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“…A detailed account of condensation reactions as applied to heterocyclic chemistry is given in Section 10.4 and in Chapter 16 [97], and for cycloaddition reactions in Chapter 17 [98]. …”

Section: Condensation Reactions 441mentioning

confidence: 99%

Section: Synthesis Of Heterocyclic Compoundsmentioning

confidence: 99%

Organic Synthesis Using Microwaves and Supported Reagents

Varma

Baig

2012

Microwaves in Organic Synthesis

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“…Owing to the fact that none of the unsymmetrical linked bis-5-arylidene rhodanines presented a significant activity against representative tumoral cell lines, we decided to change one of the two heterocyclic platforms by various (arylmethyl)aminobutyl moieties grafted on N -3 position of 5-arylidene-rhodanine derivatives in order to obtain significant potential biological activities on tumoral cell lines and effects on some protein kinases ( Hs CDK5-p25, Ss GSK3α/β, Ss CK1 and Hs Haspin). Herein, we present the building of this 3-(4-arylmethylamino)butyl-5-arylidene-rhodanine library in which the 5-arylidene-2-thioxo-1,3-thiazolidine-4-one moiety was mostly carried out under microwave irradiation [24] and the biological activities of these compounds.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2015

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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 OPEN ACCESSMolecules 2015, 20 12413 two-steps" approach assisted by microwave dielectric from N-(arylmethyl)butane-1,4-diamine hydrochloride 6a-f (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 9a-n have been obtained with a Z-geometry about their exocyclic double bond. These new 5-arylidene rhodanines derivatives 9a-n 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.

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