Synthesis and evaluation of α-, β-glucosidase inhibition of 1-N-carboxamide-1-azafagomines and 5-epi-1-azafagomines

Mendes, Raquel R.; Duarte, Vera C. M.; Fortes, A. Gil; Alves, M. I. Caetano

doi:10.1016/j.carres.2014.06.015

Cited by 4 publications

(4 citation statements)

References 8 publications

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“…[26] Notably,t he racemate of 50 also possesses higher activity than the levo enantiomer. Compound 50,f or example, is designed on the basis of the polyhydroxy diazine framework, which is an onclassical isostere of glucose.…”

Section: Other Sugar-mimic Compoundsmentioning

confidence: 99%

“…Amonga ll of the N1-substituted derivatives of 50,c ompound 51 displays the highest inhibitory activity. [26] Notably,t he racemate of 50 also possesses higher activity than the levo enantiomer. [26] In addition, compounds 52 and 53 (Table 5), designed on the basis of ac yclitol framework, show excellent inhibitory activity against yeast a-glucosidase.…”

Section: Other Sugar-mimic Compoundsmentioning

confidence: 99%

“…[26] Notably,t he racemate of 50 also possesses higher activity than the levo enantiomer. [26] In addition, compounds 52 and 53 (Table 5), designed on the basis of ac yclitol framework, show excellent inhibitory activity against yeast a-glucosidase. These cyclitols mimic the structureo ft he transition-state analogue during glycoside hydrolysis,a nd this could explain their potent inhibitory activity.…”

Section: Other Sugar-mimic Compoundsmentioning

confidence: 99%

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Recent Advances in Synthetic α‐Glucosidase Inhibitors

Liu

2017

ChemMedChem

116

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Over the past few years, the number of people diagnosed with type 2 diabetes has increased owing to an unhealthy diet, a limited amount of exercise, and obesity. The search for novel and efficient antidiabetes agents has become an urgent task for scientists. Among the antidiabetes drugs, α-glucosidase inhibitor drugs have been proven to have many advantages over other drugs, and therefore, a large number of new compounds as α-glucosidase inhibitors has recently been reported. In this review, we summarize these newly found α-glucosidase inhibitors and their structure-activity relationships in antidiabetic studies and provide better structures for α-glucosidase inhibitors or even preclinical candidates. Beyond that, some enlightening strategies for the synthesis of relevant compounds are highlighted.

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Section: Other Sugar-mimic Compoundsmentioning

confidence: 99%

Section: Other Sugar-mimic Compoundsmentioning

confidence: 99%

Section: Other Sugar-mimic Compoundsmentioning

confidence: 99%

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Recent Advances in Synthetic α‐Glucosidase Inhibitors

Liu

2017

ChemMedChem

116

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“…The dihydroxylation indicated that the chirality leads the OsO 4 to attack at the opposite face (figure ). Hence, the structure flips until the hydroxyl group reaches the equatorial position . Deprotection of compound 6 , which was the last stage of the synthesis, was performed using TFA, but a great deal of decomposition occurred.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Bioactivity of New Analogue of Bicyclic 1‐Azafagomine

et al. 2019

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New (S)‐(1,2,3,6‐tetrahydropyridazin‐3‐yl)methanol was synthesized by Lewis acid catalyzed and self‐assembled Diels‐Alder (LACASA‐DA) cycloaddition reaction using (S)‐BINOL as a chiral inductor. The N‐2 pyridazine position was protected, the hydroxyl group was carbonylated to form the new bicyclic structure. The protective group was removed and the double bond was dihydroxylated leading to the target compound. Removal of the protective group was performed using a newly found ecofriendly catalyst for N‐Boc deprotection. The final iminosugar derivative 7 and all newly synthesized intermediates, were investigated against S. aureus and E. coli bacteria and were found to show promising activity against both gram‐positive and gram‐negative bacteria.

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