A multinuclear NMR study of derivatives of thiazolidine

Barbry, Didier; Ricart, Guy; Couturier, Daniel

doi:10.1039/p29900000133

Cited by 6 publications

(3 citation statements)

References 28 publications

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“…16-18 15 N NMR data were in accord with expected values from the literature. [22][23][24][25] Acridine N-10 at ca. -72 ppm as well as thiazolidinone 2-C=N at ca.…”

Section: Synthesis and Characterization Of 3-(acridin-9-yl) Methyl-2-mentioning

confidence: 99%

Unexpected regiospecific formation and DNA binding of new 3-(acridin-9-yl)methyl-2-iminothiazolidin-4-ones

et al. 2016

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New 3-(acridin-9-yl)methyl-2-substituted imino-1,3-thiazolidin-4-ones were regiospecifically synthesized from unstable (acridin-9-yl)methyl thioureas and methyl bromoacetate (MBA) or bromoacetyl bromide (BAB). Unexpected formation of only one thiazolidinone regioisomer with both the reagents was due to a new mechanism involving a transient spiro 9,10-dihydroacridine intermediate. These results are in contrast with the reactions of acridin-9-yl thioureas with MBA/BAB that afforded two different thiazolidinone regioisomers with these reagents. UV-vis titrations, CD spectra, and fluorescence quenching have shown that new products intercalated into calf thymus (CT) DNA, and displaced ethidium bromide (EB) from a CT DNA-EB complex. Intrinsic binding constants, K b , and Stern-Volmer constants, K SV , were found in the range 0.79×10 5-2.85×10 5 M −1 and 17950-3360 M −1 , respectively. The strongest binding affinity was found for an electrondonated 2-(4-methoxyphenylimino)thiazolidinone. Additional evidence for DNA intercalation was obtained from thermal denaturation studies. Gel electrophoresis has proven that thiazolidinone products nicked the supercoiled plasmid DNA in 5.0 μM concentration.

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“…16-18 15 N NMR data were in accord with expected values from the literature. [22][23][24][25] Acridine N-10 at ca. -72 ppm as well as thiazolidinone 2-C=N at ca.…”

Section: Synthesis and Characterization Of 3-(acridin-9-yl) Methyl-2-mentioning

confidence: 99%

Unexpected regiospecific formation and DNA binding of new 3-(acridin-9-yl)methyl-2-iminothiazolidin-4-ones

et al. 2016

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show abstract

“…While the nitrogen atom is surrounded by trigonal planar coordination in the N-acylated compounds, the free thiazolidinecarboxylic acid contains a pyramidal coordinated nitrogen atom with the amino proton predominantly in pseudo axial position due to an n N -σ* C-S anomeric effect. 33 Each of the coordination types leads to conformational ensembles with different ring puckering.…”

Section: Relative Configuration and 'Upfield Rule'mentioning

confidence: 99%

“…Regarding 1 H NMR spectroscopy, different shift behaviour has been reported for the cis/trans-diastereomers of 2-substituted 1,3-thiazolidine-4-carboxylic acids. [31][32][33][34] The cis/transdifference in chemical shift of 2-H and 4-H of diastereomeric thiazolidinylphosphonates investigated by us depends on the substituents of the N,S-heterocycle and the solvent. The derivatives might be divided into two groups.…”

Section: Relative Configuration and 'Upfield Rule'mentioning

confidence: 99%