Synthesis, α-glucosidase inhibitory and molecular docking studies of prenylated and geranylated flavones, isoflavones and chalcones

Hua, Sun; Li, Yashan; Zhang, Xiaoting; Lei, Yanan; Ding, Weina; Zhao, Xue; Wang, Haomeng; Song, Xiaotong; Yao, Qingwei; Zhang, Yongmin; Ma, Ying; Wang, Run‐Ling; Zhu, Tao; Yu, Peng

doi:10.1016/j.bmcl.2015.08.059

Cited by 53 publications

(39 citation statements)

References 12 publications

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“…[38] Additionally, any modification to the 4'-hydroxy group induces al oss in a-glucosidase inhibitory activity,w hereas modification to the 5-hydroxy group results in moderate activity.B eyond that, some synthetic flavones such as compound 71 with other substituents at the 4'-positiona re also good inhibitors against baker's yeast a-glucosidase, [39] and nitroxy alkylation of the hydroxy group at the C7 position or C4' positiong ives compounds 72 and 73 with increased inhibitory activity as ar esult of the formation of new hydrogen bonds. [37] If the geranyl group is replaced with ap renyl group, the resultant compound shows decreased inhibitory activity. [37] If the geranyl group is replaced with ap renyl group, the resultant compound shows decreased inhibitory activity.…”

Section: Chromonesmentioning

confidence: 99%

“…[43] Amongt he derivatives, compound 79 showst he highest inhibitory activity against baker's yeast a- Table 7. [37][38][39][40][41] glucosidase. [37][38][39][40][41] glucosidase.…”

Section: Macrocyclic Compoundsmentioning

confidence: 99%

“…Among these flavoned erivatives, compound 68 (Table 7) with an 8-geranyl substituent exhibits excellent yeast a-glucosidase inhibitory activity,w hereas the compound obtained by replacing the 8-geranyl group with an 8-prenyl group has lower activity than 68 but is more effective than compound 69,w hich does not have any substituent at the C8 position. [37] However, all of these compounds are much more effective than the standard acarbose (IC 50 = 51.32 mm). The result of modifying the 7-hydroxy group can lead to compound 70 with an onanoic acid group, and this compound exhibits better activity than other carboxylic-acid-substituted derivatives.…”

Section: Chromonesmentioning

confidence: 99%

“…[40] Compound 74 as ad erivative of isoflavone is eightfold more active than unsubstituted genistein,w hichi ndicates that the geranyls ide chain improves the a-glucosidase inhibitory activity.H owever,m ethylation of the phenolic hydroxy groups induces ad ecrease in the inhibitory activity. [37] If the geranyl group is replaced with ap renyl group, the resultant compound shows decreased inhibitory activity. Docking studies demonstrate that there is aweak hydrogen bond between the 7-hydroxy group and the amino residues of the a-glucosidase.…”

Section: Chromonesmentioning

confidence: 99%

“…a-Glucosidase inhibitory activities of chromonederivatives. [37][38][39][40][41] glucosidase. However,t he molecular basis of the inhibitory activity of the zerumbone derivatives remainsu nclear.…”

Section: Macrocyclic 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: Chromonesmentioning

confidence: 99%

“…[43] Amongt he derivatives, compound 79 showst he highest inhibitory activity against baker's yeast a- Table 7. [37][38][39][40][41] glucosidase. [37][38][39][40][41] glucosidase.…”

Section: Macrocyclic Compoundsmentioning

confidence: 99%

Section: Chromonesmentioning

confidence: 99%

Section: Chromonesmentioning

confidence: 99%

Section: Macrocyclic Compoundsmentioning

confidence: 99%

See 3 more Smart Citations

Recent Advances in Synthetic α‐Glucosidase Inhibitors

Liu

2017

ChemMedChem

116

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Advances in the natural α‐glucosidase inhibitors

Şöhretoğlu,

Renda,

Arroo

et al. 2023

eFood

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Abstractα‐Glucosidase (AG) inhibitors, one of the classes of oral antidiabetics used to treat type 2 diabetes mellitus, delay digestion and absorption of glucose, which in turn, has a lowering effect on postprandial blood glucose and insulin levels. Natural products are a great source for the development of new AG inhibitory drug candidates. We aim to summarize advances in natural AG inhibitors according to their secondary metabolite groups in the last decade. Their mechanisms of action and structure–activity relationships will especially be discussed.

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Synthesis of Novel Methylsulfonylacrylimidamide via Click Chemistry Approach, Computational Analysis and α‐ Glucosidase Inhibition Activity

Kumar Surve,

Birmule,

Sankpal

et al. 2023

ChemistrySelect

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A series of Novel Methylsulfonylacrylimidamide analogs (4 a–4 h) were designed, synthesized, and screened for their α‐glucosidase inhibitory activity. The results indicated that some of the synthesized derivatives displayed inhibitory activities against α‐glucosidase with IC50 values ranging from 10.35±0.15 to 60.39±1.77 μM when compared to standard drug acarbose (IC50 832.22±2.00 μM). Among the synthesized derivatives, compounds 4 f and 4 h with a Di cyclohexyl and dioctyl substitution in the acrylimidamide displayed the most significant inhibitory activity with the IC50 value of 14.54±0.19 μM and 10.35±0.15 μM. The inhibitory action of compounds 4 f and 4 h against α‐glucosidase was studied by enzyme kinetic and molecular docking. In vitro, cytotoxicity showed that 4 f and 4 h exhibited low cytotoxicity against human cell lines. The ADME study suggested that most compounds will likely be orally active as they obeyed Lipinski's rule of five. Our studies showed that these derivatives could be considered a new class of α‐glucosidase inhibitors.

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Synthesis, α-glucosidase inhibitory and molecular docking studies of prenylated and geranylated flavones, isoflavones and chalcones

Cited by 53 publications

References 12 publications

Recent Advances in Synthetic α‐Glucosidase Inhibitors

Recent Advances in Synthetic α‐Glucosidase Inhibitors

Advances in the natural α‐glucosidase inhibitors

Synthesis of Novel Methylsulfonylacrylimidamide via Click Chemistry Approach, Computational Analysis and α‐ Glucosidase Inhibition Activity

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