1,3-Dipolar cycloaddition reactions on carbohydrate-based templates: synthesis of spiro-isoxazolines and 1,2,4-oxadiazoles as glycogen phosphorylase inhibitors

Benltifa, Mahmoud; Vidal, Sébastien; Gueyrard, David; Goekjian, Peter G.; Msaddek, Moncef; Praly, Jean‐Pierre

doi:10.1016/j.tetlet.2006.06.058

Cited by 83 publications

(29 citation statements)

References 29 publications

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“…226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244 245 246 247 248 249 250 251 252 253 254 255 256 257 258 259 260 261 Per-O-benzoylated or -benzylated nitriles 36 were also transformed into two other series of 1,2,4-oxadiazoles (Scheme 6). 1,3-dipolar cycloaddition with nitrile-oxides generated in situ furnished 5-b-D-glucopyranosyl-3-substituted-1,2,4-oxadiazoles 43 [60,62]. Addition of hydroxylamine to 36 produced amidoxime 42 which upon O-acylation with either carboxylic acids or acid chlorides followed by cyclodehydration gave 3-b-D-glucopyranosyl-5-substituted-1,2,4-oxadiazoles 44 [63].…”

Section: C-b-d-glucopyranosyl Derivativesmentioning

confidence: 99%

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Glucose derived inhibitors of glycogen phosphorylase

Somsák

2010

Comptes Rendus. Chimie

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Section: C-b-d-glucopyranosyl Derivativesmentioning

confidence: 99%

“…A series of glucopyranosylidene-spiro-isoxazolines 58 was prepared by 1,3-dipolar cycloaddition of nitrile-oxides to exo-glycals 57 (Scheme 8) [62]. The exomethylene sugars were made by Julia olefination of per-O-benzylated or -silylated lactone 55.…”

Section: Glucopyranosylidene-spiro-heterocyclesmentioning

confidence: 99%

Glucose derived inhibitors of glycogen phosphorylase

Somsák

2010

Comptes Rendus. Chimie

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“…24 1,3-Dipolar cycloaddition of nitrile oxides to nitriles provides an efficient and short route to diversely substituted 1,2,4-oxadiazoles.…”

Section: Q3mentioning

confidence: 99%

“…20,25 Among the first efficient glucose analogs were the N-acyl-glucopyranosylamines, for 70 example, 1a,b,h,i (Chart 1), and further inhibitor design led to the discovery of more potent N-acyl-N 0 -b-D-glucopyranosyl-ureas like 2a,b,h,i. As another class of efficient molecules, we developed several inhibitors having C-glucosyl heterocyclic structural elements such as tetrazole 3, benzimidazole 4, benzothiazole 5, 1,3,4-oxadiazole 21,22 6a and 1,2,4-oxadiazoles 7a,b,i and 8b, 23,24 as well as hydroquinone derivatives. 26 Several of these compounds displayed an inhibition against rabbit muscle glycogen phosphorylase b (RMGPb) in the low micromolar range.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structure–activity relationships of C-glycosylated oxadiazoles as inhibitors of glycogen phosphorylase

Tóth

Kun

Bokor

et al. 2009

Bioorganic & Medicinal Chemistry

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Inhibitors a b s t r a c tA series of per-O-benzoylated 5-b-D-glucopyranosyl-2-substituted-1,3,4-oxadiazoles was prepared by acylation of the corresponding 5-(b-D-glucopyranosyl)tetrazole. As an alternative, oxidation of 2,6-anhydro-aldose benzoylhydrazones by iodobenzene I,I-diacetate afforded the same oxadiazoles. 1,3-Dipolar cycloaddition of nitrile oxides to per-O-benzoylated b-D-glucopyranosyl cyanide gave the corresponding 5-b-D-glucopyranosyl-3-substituted-1,2,4-oxadiazoles. The O-benzoyl protecting groups were removed by base-catalyzed transesterification. The 1,3,4-oxadiazoles were practically inefficient as inhibitors of rabbit muscle glycogen phosphorylase b while the 1,2,4-oxadiazoles displayed inhibitory activities in the micromolar range. The best inhibitors were the 5-b-D-glucopyranosyl-3-(4-methylphenyl-and -2-naphthyl)-1,2,4-oxadiazoles (K i = 8.8 and 11.6 lM, respectively). A detailed analysis of the structureactivity relationships is presented.

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“…The choice of the protective group was important to the outcome of the cycloaddition and for the deprotection of the adducts. Deprotection of 7 by basic hydrolysis followed by acidic treatment [23] provided the known water soluble carbohydrates 8 and 9 in good yields (Table 1).…”

Section: Resultsmentioning

confidence: 99%

Asymmetric one-pot synthesis of cyclopropanes

Hamadi

Guesmi

Nouira

2016

Maced. J. Chem. Chem. Eng.

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Cycloaddition of the diazoalkanes to electron-deficient olefins (in situ) affords polysubstituted cyclopropanes in high yields (up to 85%). Deprotection of the ketal protecting group provided water-soluble cyclopropane-bearing carbohydrate in good yields. Antimicrobial activity screening of the synthesized compounds 8 and 9, utilizing a variety of Gram-positive bacteria (Staphylococcus aureus and Enterococcus fecalis), Gram-negative bacteria (Escherichia coli and Klebsiella pneumoniae) and yeast (Candida albicans), showed that all of the prepared analogues acquire promising activities against both Grampositive and Gram-negative bacteria, especially compounds 9b and 9c (antimicrobial active agents against Gram-negative bacteria).Keywords: asymmetric synthesis; carbohydrate; cyclopropane; antimicrobial АСИМЕТРИЧНА СИНТЕЗА ВО ЕДЕН САД НА ЦИКЛОПРОПАНИЦиклоадицијата на дизоалкани со олефини што имаат недостиг на електрони in situ дава полисупституирани циклопропани во голем принос (до 85%). Со отстранување на кеталната заштитна група се добиваат во вода растворливи циклопропански јаглехидрати со добар принос. Анализата на антимикробното дејство на синтетизираните соединенија 8 и 9 врз разни Грам-позитивни (Staphylococcus aureus и Enterococcus fecalis) и Грам-негативни бактерии (Escherichia coli и Klebsiella pneumoniae), како и врз квасец (Candida albicans), покажува дека сите приготвени аналози можат да дејствуваат врз Грам-позитивни и Грам-негативни бактерии, особено соединенијата 9b и 9c (антимикробни средства против Грам-негативни бактерии).

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1,3-Dipolar cycloaddition reactions on carbohydrate-based templates: synthesis of spiro-isoxazolines and 1,2,4-oxadiazoles as glycogen phosphorylase inhibitors

Cited by 83 publications

References 29 publications

Glucose derived inhibitors of glycogen phosphorylase

Glucose derived inhibitors of glycogen phosphorylase

Synthesis and structure–activity relationships of C-glycosylated oxadiazoles as inhibitors of glycogen phosphorylase

Asymmetric one-pot synthesis of cyclopropanes

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