Potent α-amylase inhibitors and radical (DPPH and ABTS) scavengers based on benzofuran-2-yl(phenyl)methanone derivatives: Syntheses, in vitro, kinetics, and in silico studies

Ali, Irfan; Rafique, Rafaila; Khan, Khalid Mohammed; Chigurupati, Sridevi; Ji, Xiangming; Wadood, Abdul; Rehman, Ashfaq Ur; Salar, Uzma; Iqbal, Muhammad Shahid; Taha, Muhammad; Perveen, Shahnaz; Ali, Bakhat

doi:10.1016/j.bioorg.2020.104238

Cited by 23 publications

(6 citation statements)

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“…The present study used various photochemical methods to analyze and derive the 3D structures of 22 compounds from A. paniculate, 4 from T. laurifolia, 9 from T. crispa L, 11 from S. suberosa and 15 from C. verum and examined the effects of these compounds on blood glucose levels and the inhibition of AG using AutoDock, AutoDock Vina and ArgusLab [32,33,34,35,36]. Chemical binding was visualized by Discovery Studio [37].…”

Section: Introductionmentioning

confidence: 99%

Computational study and in vitro alpha-glucosidase inhibitory effects of medicinal plants from a Thai folk remedy

Eawsakul

Panichayupakaranant

Ongtanasup

et al. 2021

Heliyon

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The number of patients with type 2 diabetes mellitus (T2DM) has increased worldwide. Although an instant cure was achieved with the standard treatment acabose, unsatisfactory symptoms associated with cardiovascular disease after acabose administration have been reported. Therefore, it is important to explore new treatments. A Thai folk recipe has long been used for T2DM treatment, and it effectively decreases blood glucose. However, the mechanism of this recipe has never been proven. Therefore, the potential anti-T2DM effect of this recipe, which is used in Thai hospitals, was determined to involve alpha-glucosidase (AG) inhibition with a half maximal inhibitory concentration (IC 50 ). In vitro experiments showed that crude Cinnamomum verum extract (IC 50 ¼ 0.35 AE 0.12 mg/mL) offered excellent inhibitory activity, followed by extracts from Tinospora crispa (IC 50 ¼ 0.69 AE 0.39 mg/ mL), Stephania suberosa (IC 50 ¼ 1.50 AE 0.17 mg/mL), Andrographis paniculate (IC 50 ¼ 1.78 AE 0.35 mg/mL), and Thunbergia laurifolia (IC 50 ¼ 4.66 AE 0.27 mg/mL). However, the potencies of these extracts were lower than that of acabose (IC 50 ¼ 0.55 AE 0.11 mg/mL). Therefore, this study investigated and developed a formulation of this recipe using computational docking. Among 61 compounds, 7 effectively inhibited AG, including chlorogenic acid (IC 50 ¼ 819.07 pM) through 5 hydrogen bonds (HBs) and 2 hydrophobic interactions (HIs); β-sitosterol (IC 50 ¼ 4.46 nM, 6 HIs); ergosterol peroxide (IC 50 ¼ 4.18 nM, 6 HIs); borapetoside D (IC 50 ¼ 508.63 pM, 7 HBs and 2 HIs); borapetoside A (IC 50 ¼ 1.09 nM, 2 HBs and 2 His), stephasubimine (IC 50 ¼ 285.37 pM, 6 HIs); and stephasubine (IC 50 ¼ 1.09 nM, 3 HBs and 4 HIs). These compounds bind with high affinity to different binding pockets, leading to additive effects. Moreover, the pharmacokinetics of six of these seven compounds (except ergosterol peroxide) showed poor absorption in the gastrointestinal tract, which would allow for competitive binding to AG in the small intestine. These results indicate that the development of these 6 compounds into oral antidiabetic agents is promising.

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Section: Introductionmentioning

confidence: 99%

Computational study and in vitro alpha-glucosidase inhibitory effects of medicinal plants from a Thai folk remedy

Eawsakul

Panichayupakaranant

Ongtanasup

et al. 2021

Heliyon

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“…In particular, the protocol used in the Method D in which TEA used as a base catalyst in the absence of any solvents at 130 °C significantly enhances the yields considerably in a shorter span of time compared to the reported routes and has a certain value from the green chemistry principles. On this basis, it [35] , 78 [36,37] 2 Br H H CH 3 Cl 3 b 87 85 [36,37] , 91 [38] [39] , 41 [40] , 81 [41] [39] , 93 [41] 13 Br H H p-BrC 6 H 5 Br 3 m 94 88 [17] , 89 [42] 14 Br H H p-CH 3 C 6 H 5 Br 3 n 95 87 [17] , 86 [40] [43] , 68 [44] [45] could be utilized as general synthetic routes for the preparation of many benzofurans and their derivatives or the construction of novel heterocyclic compounds having pharmaceutical importance. Furthermore, the use of TEA as a novel base catalyst for the synthesis of benzofurans in the developed methods offers numerous advantages such as being solventfree, involving clean reaction procedures, having high conversion rates and being free of wasteful of byproducts and solvents for the prospective future studies.…”

Section: Discussionmentioning

confidence: 99%

Rap‐Stoermer Reaction: TEA Catalyzed One‐Pot Efficient Synthesis of Benzofurans and Optimization of Different Reaction Conditions

Koca¹,

Ertürk²,

Bozca³

2022

ChemistrySelect

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The reaction of substituted salicylaldehydes with α‐haloketones to obtain benzofuran‐2‐yl (Alkyl/aryl) ketones, which is a Dickman type aldol condensation product in base, solvent, and temperature environment, is called as Rap‐Stoermer reaction. In this study, a series of Benzofuran‐2‐yl (Alkyl/ aryl) ketones was synthesized by heating substituted salicylaldehydes and α‐haloketones under solvent‐free sealed (closed vessel) conditions by using triethyleamine (TEA) as a novel base catalyst in good to excellent yields (81–97 %) at 130 °C and the obtained results compared with the existing literature. The reaction conditions were optimized in terms of yield, time, base, solvent temperature, stoichiometric ratios, and synthesis environments (open or closed vessels). The optimized protocol offers promising advantages such as solvent‐free and clean reaction media, short reaction time, no byproducts, and appreciable high yields for the prospective studies. Characterization of the synthesized compounds was performed by using spectroscopic methods such as ATR‐FTIR, 1H‐NMR, 13C‐NMR and LC‐MS.

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“…Literature dates indicate that active benzofurans and their derivatives exhibit both oxidant and antioxidant properties [31,[39][40][41]. In the present study ROS generation examination was performed after 6 and 12 h exposure to tested derivatives at IC 50 concentration.…”

Section: Reactive Oxygen Species (Ros) Generationmentioning

confidence: 92%

New Derivatives of 1-(3-Methyl-1-Benzofuran-2-yl)Ethan-1-one: Synthesis and Preliminary Studies of Biological Activity

Napiórkowska,

Kumaravel,

Amboo Mahentheran

et al. 2024

IJMS

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A set of nine derivatives, including five brominated compounds, was synthesized and the structures of these novel compounds were confirmed using 1H and 13C NMR as well as ESI MS spectra. These compounds were tested on four different cancer cell lines, chronic myelogenous leukemia (K562), prostate cancer (PC3), colon cancer (SW620), human kidney cancer (Caki 1), and on healthy human keratocytes (HaCaT). MTT results reveal that two newly developed derivatives (6 and 8) exhibit selective action towards K562 cells and no toxic effect in HaCat cells. The biological activity of these two most promising compounds was evaluated by trypan blue assay, reactive oxygen species generation, and IL-6 secretion. To investigate the proapoptotic activity of selected compounds, the two following types of tests were performed: Annexin V Apoptosis Detection Kit I and Caspase-Glo 3/7 assay. The studies of the mechanism showed that both compounds have pro-oxidative effects and increase reactive oxygen species in cancer cells, especially at 12 h incubation. Through the Caspase-Glo 3/7 assay, the proapoptotic properties of both compounds were confirmed. The Annexin V-FITC test revealed that compounds 6 and 8 induce apoptosis in K562 cells. Both compounds inhibit the release of proinflammatory interleukin 6 (IL-6) in K562 cells. Additionally, all compounds were screened for their antibacterial activities using standard and clinical strains. Within the studied group, compound 7 showed moderate activity towards Gram-positive strains in antimicrobial studies, with MIC values ranging from 16 to 64 µg/mL.

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Potent α-amylase inhibitors and radical (DPPH and ABTS) scavengers based on benzofuran-2-yl(phenyl)methanone derivatives: Syntheses, in vitro, kinetics, and in silico studies

Cited by 23 publications

References 50 publications

Computational study and in vitro alpha-glucosidase inhibitory effects of medicinal plants from a Thai folk remedy

Computational study and in vitro alpha-glucosidase inhibitory effects of medicinal plants from a Thai folk remedy

Rap‐Stoermer Reaction: TEA Catalyzed One‐Pot Efficient Synthesis of Benzofurans and Optimization of Different Reaction Conditions

New Derivatives of 1-(3-Methyl-1-Benzofuran-2-yl)Ethan-1-one: Synthesis and Preliminary Studies of Biological Activity

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