Synthesis of sugars embodying conjugated carbonyl systems and related triazole derivatives from carboxymethyl glycoside lactones. Evaluation of their antimicrobial activity and toxicity

Xavier, Nuno M.; Goulart, Margarida; Neves, Ana; Justino, Jorge; Chambert, Stéphane; Rauter, Amélia P.; Queneau, Yves

doi:10.1016/j.bmc.2010.11.060

Cited by 15 publications

(8 citation statements)

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“…With reference to the biological safety profile of sugar conjugates derived from natural and synthetic agents [ 18 – 20 ], and in continuation with our earlier studies on quinoxaline [ 21 – 25 ], herein we report some saccharide (sugar) linked quinoxaline. In this work, the hydrazino intermediate was preferred to achieve sugar conjugates in order to mimic the structural resemblance to nucleosides and other active hydrazide drugs.…”

Section: Introductionmentioning

confidence: 64%

New Conjugates of Quinoxaline as Potent Antitubercular and Antibacterial Agents

Peraman¹,

Kuppusamy

Killi

et al. 2016

International Journal of Medicinal Chemistry

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Considering quinoxaline as a privileged structure for the design of potent intercalating agents, some new sugar conjugates of quinoxaline were synthesized and characterized by IR, 1HNMR, 13C NMR, and mass spectral data. In vitro testing for antitubercular and antimicrobial activities was performed against Mycobacterium tuberculosis H 37 Rv and some pathogenic bacteria. Results revealed that conjugate containing ribose moiety demonstrated the most promising activity against Mycobacteria and bacteria with minimum inhibitory concentrations (MIC) of 0.65 and 2.07 μM, respectively. Other conjugates from xylose, glucose, and mannose were moderately active whilst disaccharides conjugates were found to be less active. In silico docking analysis of prototype compound revealed that ATP site of DNA gyrase B subunit could be a possible site for inhibitory action of these synthesized compounds.

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Section: Introductionmentioning

confidence: 64%

New Conjugates of Quinoxaline as Potent Antitubercular and Antibacterial Agents

Peraman¹,

Kuppusamy

Killi

et al. 2016

International Journal of Medicinal Chemistry

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“…In the framework of our research dedicated to the use of carbohydrates as organic raw materials [1,2,43,44], our group has also investigated some applications of isomaltulose [45][46][47] and reported an oxidative degradation of isomaltulose leading to carboxymethyl glucoside (CMG), a precursor of a bicyclic lactone which was further used as a scaffold offering alternative routes towards pseudoglycoconjugates [48][49][50][51][52][53][54][55][56][57].…”

Section: Occurrence and Synthesis Of Gmf And Analogous Glycosylated Dmentioning

confidence: 99%

Glucosyloxymethylfurfural (GMF): a creative renewable scaffold towards bioinspired architectures

Tan

Ahmar

Queneau

2015

Pure and Applied Chemistry

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Glucosyloxymethylfurfural (GMF) is the glucosylated analogue of hydroxymethylfurfural (HMF), and is obtained in one step from the very available disaccharide isomaltulose. This account gives an overview on the preparation and the uses of GMF towards architectures containing a carbohydrate moiety and shows that rather elaborated targets can be synthesized from GMF in very short sequences. A special focus is made on carbon-carbon formation on the aldehyde group leading to new biobased acrylic derivatives by the Baylis-Hillman reaction.

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“…6 However, in a few instances, a side-reaction was reported in low percentage: namely iodination at the 5-position of the 1,4-isomer of the formed 1,2,3-triazole. [7][8][9][10] Since this iodination was observed in a few cases, and that we did not detect it to the best of our knowledge, we became interested in identifying the origins of this side-reaction. We made the hypotheses that the iodination may be due to different reagents and providers, catalyst preparation, substrate, or reaction conditions.…”

Section: Introductionmentioning

confidence: 99%