Facile synthesis of oxo-/thioxopyrimidines and tetrazoles C–C linked to sugars as novel non-toxic antioxidant acetylcholinesterase inhibitors

Figueiredo, José A.; Ismael, Maria I.; Pinheiro, Jorge M.; Silva, A.M.S.; Justino, Jorge; Silva, F.V.M.; Goulart, Margarida; Mira, D.; Araújo, Maria Eduarda; Campoy, R.; Rauter, Amélia P.

doi:10.1016/j.carres.2011.11.006

Cited by 22 publications

(7 citation statements)

References 47 publications

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“…Among these compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14), compound 2 with 3-methyl phenyl substitution and compound 3 with 3-chloro phenyl substitution were found as the most active compounds. The inhibition percentages were calculated as 29.56% and 14.53% at 1 and 0.1 mM concentrations for compound 2 and the inhibition percentages were calculated 24.38% and 12.96% at 1 and 0.1 mM concentrations for compound 3.…”

Section: Resultsmentioning

confidence: 99%

“…Objectives: In this study, we aimed to synthesize fourteen different 2-[(1-methyl-1H-tetrazole-5-yl) thio]-1-(substituted phenyl) ethanone derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) and to investigate their anticholinesterase activities. Method: 1-(Substituted phenyl)-2-[(1-methyl-1H-tetrazol-5-yl) thio]ethanone compounds were synthesized by reacting 1-methyl-1H-tetrazol-5-thiol with some phenacyl bromide derivatives.…”

Section: Biological Evaluation Of Some Tetrazole Derivatives As Cholimentioning

confidence: 99%

“…Tetrazoles have a wide variety of applications as pharmaceutical products and explosives, in cholinesterase inhibitor activity (8).…”

Section: Introductionmentioning

confidence: 99%

“…The medicinal, biochemical and pharmacological properties of tetrazole compounds support a vast progress in their chemistry over the last years (5)(6)(7). Tetrazoles have a wide variety of applications as pharmaceutical products and explosives, in cholinesterase inhibitor activity (8).…”

Section: Introductionmentioning

confidence: 99%

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Biological Evaluation Of Some Tetrazole Derivatives As Cholinesterase Inhibitors

Mohsen¹,

Yurttaş

Özdemır³

et al. 2014

MUSBED

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Section: Resultsmentioning

confidence: 99%

Section: Biological Evaluation Of Some Tetrazole Derivatives As Cholimentioning

confidence: 99%

“…Tetrazoles have a wide variety of applications as pharmaceutical products and explosives, in cholinesterase inhibitor activity (8).…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Biological Evaluation Of Some Tetrazole Derivatives As Cholinesterase Inhibitors

Mohsen¹,

Yurttaş

Özdemır³

et al. 2014

MUSBED

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“…Very recently, Figueiredo et al synthesized C-nucleosides 83 with the C-4 substituted 3,4-dihydropyrimidin-2(1 H )-thione as a nucleobase (Scheme 31) [104]. The products were obtained as the C-4-( R ) single diastereoisomers.…”

Section: Reviewmentioning

confidence: 99%

Multicomponent reactions in nucleoside chemistry

Koszytkowska‐Stawińska¹,

Buchowicz²

2014

Beilstein J. Org. Chem.

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SummaryThis review covers sixty original publications dealing with the application of multicomponent reactions (MCRs) in the synthesis of novel nucleoside analogs. The reported approaches were employed for modifications of the parent nucleoside core or for de novo construction of a nucleoside scaffold from non-nucleoside substrates. The cited references are grouped according to the usually recognized types of the MCRs. Biochemical properties of the novel nucleoside analogs are also presented (if provided by the authors).

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Vinyl Selenones Derived from d‐Fructose: A New Platform for Fructochemistry

2016

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d-Fructose, an inexpensive biomass precursor available on al arge scale, has been used for the generation of enantiomerically pure chemical entities. Construction of vinyl selenone moieties on cyclic skeletons of d-fructose led to the highly reactive synthetic intermediates comprisingo f an electron-deficient double bond along with an excellent leaving group. Reactions of these Michael acceptors with dif-ferent nucleophiles afforded aziridines, thiiranes,c yclopropanes, dihydrofurans, dihydroisoxazole, dibenzyloxymethylfuran, and isonucleosides in moderate to good yields. This powerful and practical route provides an ew platform for synthetic applicationso fr enewable biomass precursors and adds to the toolbox for chemists interested in new chemical entities. Supportinginformation for this article can be found under http:// dx.doi.org/10.1002/ajoc.201600183.I tc ontains 1 Ha nd 13 CNMR spectra of all new compounds, COSYs pectra( for 18 b, 20 a, 24,a nd 27 c), NOESY spectrum(for 17 c), 1D NOE difference spectra (for 18 b, 20 a,and 24), and ORTEP diagrams (for 15 h, 17 a, 22,and 30 b).populara ldoses such as d-glucose, d-mannose, d-ribose, dxylose, etc. Ac hiral ketones ynthesized from d-fructose [9] rapidly developed into an ew class of asymmetric epoxidation catalyst forthe epoxidation of olefins ( Figure 2). [10] Fructose-derived chiral 1,3-oxazolidine-2-thiones (OZTs) are also used as chiral substrates in coupling reactions ( Figure 2). [11] 1,5-Anhydro-dfructose( 1,5-AnFru) [12] and di-d-fructose dianhydrides (DFAs) [2, 13] are important precursors for the synthesis of new carbohydrate derivatives (Figure 2).We have been designing methodsf or accessing enantiopure oxaheterocycles, [14] carbocycles, [15, 16] aza-and thia-heterocycles, [16, 17] pyrroles, [18] and 1,5-disubstituted-1,2,3-triazoles [19] from monosaccharides. In line with the utilization of sugar molecules as "chiral pools"i ns ynthetic chemistry, [20] our strategy wast ou se highlyr eactive vinyl sulfone-and vinyl sulfoxide-modified carbohydrates, [21] which are powerful Michael acceptors ande fficient partners in cycloaddition reactions. [15, 19] More recently,w eh ave introduced vinyl selenone-modified carbohydrates as efficient Michael acceptors in diversity oriented synthesis (DOS) to generate complex molecular scaffolds. [22] The aryl selenoyl functionality of vinyl selenone plays ad ual role as an efficient electron-withdrawing group as well as al eaving group, allowing Michael addition followed by elimination in tandem fashion. [22] Although vinyl selenones are widely used in simple systems [23] and nucleosides, [24] vinyl selenones derived from carbohydrates have rarely been utilized partly because of the notoriously unpredictable stability of carbohydrate selenones or selenoxides. [25,26] Nevertheless,w e have designed and used stable vinyl selenone-modified furanosides for generating new molecules. [22,26] As d-fructose is now considered as an intermediate for generating small molecules such as 2,5-dimethylfuran, 5-hydroxymethy...

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Facile synthesis of oxo-/thioxopyrimidines and tetrazoles C–C linked to sugars as novel non-toxic antioxidant acetylcholinesterase inhibitors

Cited by 22 publications

References 47 publications

Biological Evaluation Of Some Tetrazole Derivatives As Cholinesterase Inhibitors

Biological Evaluation Of Some Tetrazole Derivatives As Cholinesterase Inhibitors

Multicomponent reactions in nucleoside chemistry

Vinyl Selenones Derived from d‐Fructose: A New Platform for Fructochemistry

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