α-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives

Raju, B. China; Tiwari, Ashok Kumar; Jaladi, Ashok Kumar; Ali, Amtul Z.; Agawane, Sachin B.; Saidachary, Gannerla; Kuncha, Madhusudana

doi:10.1016/j.bmc.2009.10.047

Cited by 93 publications

(50 citation statements)

References 33 publications

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“…A series of 3-styrylchromone derivatives (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were synthesized and evaluated for DPPH free radical scavenging and α-glucosidase inhibitory activities. As a result, compounds 15 and 20, possessing a catechol moiety in the B-ring, showed potent activity in both assays.…”

Section: Resultsmentioning

confidence: 99%

“…4) Recently, several researchers have evaluated α-glucosidase inhibitors possessing free-radical scavenging activity. [5][6][7][8][9][10][11] 4H-1-Benzopyran-4-ones (chromones) are an important class of oxygenated heterocyclic compounds, and have attracted the attention of organic chemists and biochemists due to their biological activities and occurrence in natural products. This chromone core structure is found in flavones, isoflavones, and 2-styrylchromones.…”

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confidence: 99%

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Synthesis and Biological Evaluation of 3-Styrylchromone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

Takao

Ishikawa

Sugita

2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of 3-styrylchromone derivatives (4-20) were synthesized and the structure-activity relationships for α-glucosidase inhibition and antioxidant activities were analyzed. Among the synthesized compounds, compounds 15 and 20, which contain a catechol moiety, showed both potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (15: EC 50 17 µM; 20: EC 50 23 µM) and α-glucosidase inhibitory activity (15: IC 50 16 µM; 20: IC 50 10 µM). Our data suggest that 3-styrylchromone derivatives are novel α-glucosidase inhibitors that have the potential to counteract diet-induced hyperglycemia in diabetes.Key words 3-styrylchromone; α-glucosidase inhibitor; antioxidant; structure-activity relationship Diabetes mellitus is a metabolic disorder characterized by hyperglycemia resulting from insufficiency of secretion or action of endogenous insulin. α-Glucosidase has been recognized as a therapeutic target for modulation of postprandial hyperglycemia. α-Glycosidase inhibitors act to delay glucose absorption, making them potent drugs to control blood glucose levels.1) On the other hand, antioxidants function as free radical scavengers, chelating agents for pro-oxidant metals, quenchers of singlet oxygen formation, and reducing agents. 2,3)Because of their antioxidant characteristics, antioxidants are important in the prevention of human diseases. The accumulated evidence suggests that diabetic patients are under oxidative stress and that oxidative stress plays a major role in the pathogenesis of diabetes mellitus. 4) Recently, several researchers have evaluated α-glucosidase inhibitors possessing free-radical scavenging activity. 5-11)4H-1-Benzopyran-4-ones (chromones) are an important class of oxygenated heterocyclic compounds, and have attracted the attention of organic chemists and biochemists due to their biological activities and occurrence in natural products. This chromone core structure is found in flavones, isoflavones, and 2-styrylchromones. Flavones and isoflavones are distributed in several species of plants. In contrast, 2-styrylchromones constitute a small group of naturally occurring chromones. Synthetic 2-styrylchromones possess a number of biological activities, including antioxidant, 12,13) anti-allergic, 14) anti-inflammatory, 15) antitumor, [16][17][18] and antiviral [19][20][21] effects. The synthesis and evaluation of biological activities of 2-styrylchromones has been extensively investigated, while studies dealing with 3-styrylchromones are few. Moreover, although there are some examples of the synthesis of 3-styrylchromones, [22][23][24][25][26][27] only a few studies have evaluated the biological activity of 3-styrylchromones. 22,28) In order to further explore novel biological activities, a series of 3-styrylchromone derivatives were synthesized, containing newly prepared compounds, and structure-activity relationships in regards to antioxidant activity and α-glycosidase inhibition were investigated. Results and DiscussionChemistry 3-Styrylchromone derivatives presented in this...

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Synthesis and Biological Evaluation of 3-Styrylchromone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

Takao

Ishikawa

Sugita

2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…We synthesized a series of 3-benzylidene-4-chromanone derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) and evaluated their potential for DPPH free radical scavenging and α-glucosidase inhibitory activity. As a result, compounds 5, 13, 18, which possess a catechol moiety on the B-ring, were found to exhibit potent DPPH free radical scavenging and α-glucosidase inhibitory activities.…”

Section: Resultsmentioning

confidence: 99%

“…Compound 1a was commercially available and compounds 1b and c were synthesized from resorcinol according to the procedure of Foroumadi et al 21) With 1a-c in hand, each was condensed with benzaldehyde derivatives (2a-h) in the presence of piperidine to provide the 3-benzylidene-4-chromanone derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20).…”

Section: =H Oh Andmentioning

confidence: 99%

“…Recently, several researchers have evaluated α-glucosidase inhibitors exhibiting free-radical scavenging activity. [4][5][6][7][8][9] (3E)-3-Benzylidene-2,3-dihydro-4H-1-benzopyran-4-ones (3-benzylidene-4-chromanones) constitute a small class of natural products primarily isolated from Hyacinthaceae and Caesalpinioideae. [10][11][12][13][14] Several natural and synthetic 3-benzylidene-4-chromanones are related structurally to flavonoids and were found to possess various biological properties such as antioxidant, antifungal, antiviral, anti-mutagenic, antiproliferative, anti-allergic, antihistaminic, anti-inflammatory, and monoamine oxidase inhibitory activity.…”

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confidence: 99%

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Synthesis and Biological Evaluation of 3-Benzylidene-4-chromanone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

Takao

Yamashita

Yashiro

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of 3-benzylidene-4-chromanone derivatives (3-20) were synthesized and the structure-activity relationships for antioxidant and α-glucosidase inhibitory activities were evaluated. Among synthesized compounds, compounds 5, 13, 18, which contain catechol moiety, showed the potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (5: EC 50 13 µM; 13: EC 50 14 µM; 18: EC 50 13 µM). The compounds 12, 14, 18 showed higher α-glucosidase inhibitory activity (12: IC 50 15 µM; 14: IC 50 25 µM; 18: IC 50 28 µM). The compound 18 showed both of potent DPPH radical scavenging and α-glucosidase inhibitory activities. These data suggest that 3-benzylidene-4-chromanone derivatives, such as compound 18, may serve as the lead compound for the development of novel α-glucosidase inhibitors with antioxidant activity.

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Aromatic Electrophilic Substitution Reactions

2020

Applied Organic Chemistry

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α-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives

Cited by 93 publications

References 33 publications

Synthesis and Biological Evaluation of 3-Styrylchromone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

Synthesis and Biological Evaluation of 3-Styrylchromone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

Synthesis and Biological Evaluation of 3-Benzylidene-4-chromanone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

Aromatic Electrophilic Substitution Reactions

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