Structure-Activity Relationships of<i>N</i>-Cinnamoyl and Hydroxycinnamoyl Amides on<i>α</i>-Glucosidase Inhibition

Chochkova, Maya; Petrova, Petranka; Stoykova, Boyka; Ivanova, Galya; Štícha, Martin; Dibó, Gábor; Milkova, Tsenka

doi:10.1155/2017/6080129

Cited by 7 publications

(3 citation statements)

References 35 publications

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“…Chochkova and co-workers reported the inhibitory activity of substituted cinnamic acid on αglucosidase enzyme. The results showed that these compounds have better activity (IC50 values ranging from 0.13±0.02 to 2.45±0.04 µg/mL) than acarbose (IC50 2.50±0.21 µg/mL) and cinnamic acid (IC50 65.1±0.1 µg/mL) [16]. Further, trans-cinnamamide derivatives also showed higher α-glucosidase inhibitory activity (IC50 values ranging from 0.71±0.492 to 0.95±0.008 mM) than acarbose (IC50 1.78±0.727 mM) [17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and α-glucosidase inhibitory activity of cinnnamamides

Aijijiyah

Wati

Rahayu

et al. 2022

Preprint

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Suitably substituted cinnnamamides were successfully synthesized in 11-92% yield. Majority of the cinnnamamides displayed IC50 greater than acarbose. Their α-glucosidase inhibitory activity greatly depended on their structure with electron-withdrawing groups on the cinnamoyl aromatic ring causing increased inhibition activity. The synthesized cinnnamamides showed acceptable physicochemical and pharmacokinetics characteristics with little toxicity indicating their potential use as lead drug candidates. Molecular docking studies of these compounds were also conducted to elucidate their mechanism of action. Overall, these cinnnamamides show potential as lead structures for further optimization as α-glucosidase inhibitors.

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Section: Introductionmentioning

confidence: 99%

Synthesis and α-glucosidase inhibitory activity of cinnnamamides

Aijijiyah

Wati

Rahayu

et al. 2022

Preprint

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“…Accumulated studies indicate that T2DM is usually associated with overnutrition (Silva et al, 2016). In diabetes, the postprandial phase is accompanied by a rapid and large increase in blood glucose levels (Chochkova et al, 2017). Postprandial hyperglycemia affects the development of type II diabetes negatively and causes diabetic complications, including dyslipidemia and hypertension (Baron, 1998).…”

Section: Introductionmentioning

confidence: 99%

Discovery of N‐(phenylsulfonyl)thiazole‐2‐carboxamides as potent α‐glucosidase inhibitors

Liu,

Li,

Zhao

et al. 2023

Drug Development Research

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In a search for novel nonsugar α‐glucosidase inhibitors for diabetes treatment, a series of N‐(phenylsulfonyl)thiazole‐2‐carboxamide derivatives were designed and synthesized, the α‐glucosidase inhibitory activities were then evaluated. Several compounds with promising α‐glucosidase inhibitory effects were identified. Among these, compound W24 which shows low cytotoxicity and good α‐glucosidase inhibitory activity with an IC50 value of 53.0 ± 7.7 μM, is more competitive compared with the commercially available drug acarbose (IC50 = 228.3 ± 9.2 μM). W24 was identified as a promising candidate in the development of α‐glucosidase inhibitors. Molecular docking studies and molecular dynamics simulation were also performed to reveal the binding pattern of the active compound to α‐glucosidase, and the binding free energy of the best compound W24 was 36.3403 ± 3.91 kcal/mol.

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“…For the last ffteen years, the research group has focused the attention on the synthesis of cinnamic acid derivatives, comprising various pharmacophores, and studied them as antioxidants, antiglucosidase inhibitors, antityrosinase inhibitors, and antimicrobials [8,[27][28][29][30][31].…”

Section: Introductionmentioning

confidence: 99%

Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile

Chochkova

Georgieva

Ilieva

et al. 2022

Journal of Chemistry

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A series of seventeen cinnamic acid hybrids (4ai–ci) were obtained through an amidation of aminoadamantanes (amantadine, rimantadine, and memantine) with mixed anhydride generated from different substituted cinnamic acid and ethyl chloroformate. 1H NMR, 13C NMR, IR, and HRMS were used for the confirmation of the structures of the synthesized hybrids. Moreover, the antioxidant profiles of amides were estimated as per five different in vitro methods: 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azinobis-3-ethylbenzothiazoline-6-sulfonic acid cation radical (ABTS⁺), ferric reducing antioxidant power (FRAP), cupric reducing antioxidant capacity (CUPRAC) assay, and inhibition of Fe(III)/asc induced lipid peroxidation (LP) in brain homogenate. For comparison, caffeic acid (CaffA), known as a potent naturally occurring antioxidant, was used as a reference compound in our study. The results revealed that the most prominent antioxidant activity was demonstrated by compound 4b2, with excellent CUPRAC, FRAP, scavenging ABTS+˙ potential, and inhibition of Fe/asc–induced LP, followed by 4c6 > 4a6 > CaffA > 4c5 and 4a5 > 4a7. Overall, the results suggest that the hybrids (4b2, 4c6, and 4a6) consisting of a caffeoyl moiety and lipophilic adamantane core endow the molecules with the higher antioxidant activity than their parent compound (caffeic acid), especially against LP. Thus, these promising antioxidants could have beneficial effects in various pathological conditions, where oxidative stress is implicated.

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Structure-Activity Relationships ofN-Cinnamoyl and Hydroxycinnamoyl Amides onα-Glucosidase Inhibition

Cited by 7 publications

References 35 publications

Synthesis and α-glucosidase inhibitory activity of cinnnamamides

Synthesis and α-glucosidase inhibitory activity of cinnnamamides

Discovery of N‐(phenylsulfonyl)thiazole‐2‐carboxamides as potent α‐glucosidase inhibitors

Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile

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