Design and synthesis of thiazole-5-hydroxamic acids as novel histone deacetylase inhibitors

Anandan, Sampath-Kumar; Ward, John S.; Brokx, Richard D.; Denny, Trisha A.; Bray, Mark R.; Patel, Dinesh V.; Xiao, Xiao-Yi

doi:10.1016/j.bmcl.2007.07.050

Cited by 28 publications

(16 citation statements)

References 23 publications

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“…The sym-triazine ester derivatives (III) were treated with three equivalents of freshly prepared hydroxyl amine in dry methanol to produce the final products [12,[32][33][34][35]. The final yields under these conditions were 38-66%.…”

Section: Resultsmentioning

confidence: 99%

“…The most common method of HA synthesis is treating the ester derivatives with hydroxyl amine [12,[30][31][32][33][34][35]. Although some sym-triazine containing esters have been described, which were synthesized through a multistep synthesis using melamine and isocyanates [30], only one article was found where the sym-triazine based hydroxamic acids have been described [31].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of new 4,6-disubstituted-1,3-5-triazin-2-yloxy esters and N-hydroxyamides

et al. 2010

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A convenient method for synthesis of new sym-triazine ester and hydroxamate derivatives has been developed. Various reaction conditions were studied and optimized, and a series of new 1,3,5-triazine based esters and N-hydroxyamides were obtained with good yields (38-80%). The reaction between oxo-derivatives of 4,6-disubstituted-1,3,5-triazines and halogenated carboxylic esters derivatives using Cs2CO3 as a catalyst was found to be the most convenient method for 4,6-disubstituted-1,3,5-triazine-2-yloxy esters synthesis. These 1,3,5-triazin based esters served as precursors for the synthesis of 4,6-disubstituted-1,3,5-triazin-2-yloxy-N-hydroxybutanamides using solution of hydroxylamine hydrochloride in dry methanol and KOH at room temperature. Structures of the newly synthesized compounds were obtained by 1 H NMR, 13 C NMR, MS, IR spectral data and elemental analysis.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of new 4,6-disubstituted-1,3-5-triazin-2-yloxy esters and N-hydroxyamides

et al. 2010

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“…Thus the thiazole nucleus has been much studied in the field of organic and medicinal chemistry [6]. Several methods for the synthesis of thiazole derivatives have been developed [7][8][9][10][11], the most widely used method *Address correspondence to this author at the Chemistry Department, Faculty of Sciences, Shahid Rajaee Teacher Training University, P.O. Box 16785-163, Tehran, Iran; Tel: +98-21-22970003; Fax: +98-21-22970033; E-mail: sabbaghan@srttu.edu, msaba16us@yahoo.com being the Hantzsch's synthesis, in which an -halocarbonyl compound is condensed with a thioamides, thioureas, thiocarbamic acids, or dithiocarbamic acids [12][13][14].…”

Section: Introductionmentioning

confidence: 99%

A Rapid, Four-Component Synthesis of Functionalized Thiazoles

Sabbaghan

Alidoust²,

Hossaini³

2011

CCHTS

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“…Several methods for the synthesis of thiazole derivatives have been developed [8][9][10][11][12], the most widely used method being the Hantzsch's synthesis utilizing thioamides and α-halocarbonyl compounds as the starting materials [13]. Also the factors which affect on the orientation of cyclization reactions of functionalized 1,2,4-triazine derivatives with α-halocarbonyl compounds were reviewed [14].…”

Section: Introductionmentioning

confidence: 99%