Synthesis of novel 5-(2,5-bis(2,2,2-trifluoroethoxy)phenyl)-1,3,4-oxadiazole-2-thiol derivatives as potential glucosidase inhibitors

Gani, Ramesh S.; Kudva, Avinash K.; Timanagouda, Karabasanagouda; Raghuveer,; Mujawar, Salma Begum Hussain; Joshi, Shrinivas D.; Raghu, Shamprasad Varija

doi:10.1016/j.bioorg.2021.105046

Cited by 34 publications

(26 citation statements)

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“…Multiple chromatographic approaches of the leaf extract led to the isolation of 14 compounds, including 4 flavone glycosides (1-4) and 10 dihydrochalcone glycosides (5)(6)(7)(8)(9)(10)(11)(12) with two non-separable mixtures, including four newly described compounds, i.e., 1, 8, 11a, and 11b were reported for the first time in the literature. Further, in vitro α-glucosidase inhibitory activity assessment of isolated compounds revealed the strong potency of isolated flavone glycosides, viz., compounds 1, 2, 3, and 4, as α-glucosidase inhibitors, compared to dihydrochalcone glycosides, except for compound 12.…”

Section: Discussionmentioning

confidence: 99%

“…Furthermore, some white fat storage areas in the body are more directly associated to metabolic consequences of obesity, such as diabetes, than others [2]. Obesity-related problems, viz., diabetes has been associated with decreased life expectancy [4] as well as imparting various clinical disorders such as renal disease, blindness, and amputation of lower limbs, among others [5].…”

Section: Introductionmentioning

confidence: 99%

“…Likewise, α-glucosidase inhibitors as typical anti-diabetic medicines reported to possess side effects despite their important function in lowering blood glucose levels [7]. Only three α-glucosidase inhibitors are currently used in clinical practice including acarbose, miglitol, and voglibose [5,7], warranting for the development of natural medicines that comprise medicinal herbs, either as pure components or as extracts, as an alternative therapy for obesity [3,7].…”

Section: Introductionmentioning

confidence: 99%

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Anti-Obesity Evaluation of Averrhoa carambola L. Leaves and Assessment of Its Polyphenols as Potential α-Glucosidase Inhibitors

et al. 2022

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Averrhoa carambola L. is reported for its anti-obese and anti-diabetic activities. The present study aimed to investigate its aqueous methanol leaf extract (CLL) in vivo anti-obese activity along with the isolation and identification of bioactive compounds and their in vitro α-glucosidase inhibition assessment. CLL improved all obesity complications and exhibited significant activity in an obese rat model. Fourteen compounds, including four flavone glycosides (1–4) and ten dihydrochalcone glycosides (5–12), were isolated and identified using spectroscopic techniques. New compounds identified in planta included (1) apigenin 6-C-(2-deoxy-β-D-galactopyranoside)-7-O-β-D-quinovopyranoside, (8) phloretin 3′-C-(2-O-(E)-cinnamoyl-3-O-β-D-fucopyranosyl-4-O-acetyl)-β-D-fucopyranosyl-6′-O-β-D fucopyranosyl-(1/2)-α-L arabinofuranoside, (11a) phloretin3′-C-(2-O-(E)-p-coumaroyl-3-O-β-D-fucosyl-4-O-acetyl)-β-D-fucosyl-6′-O-(2-O-β-D-fucosyl)-α-L-arabinofuranoside, (11b) phloretin3′-C-(2-O-(Z)-p-coumaroyl-3-O-β-D-fucosyl-4-O-acetyl)-β-D-fucosyl-6′-O-(2-O-β-D-fucosyl)-α-L-arabinofuranoside. Carambolaside M (5), carambolaside Ia (6), carambolaside J (7), carambolaside I (9), carambolaside P (10a), carambolaside O (10b), and carambolaside Q (12), which are reported for the first time from A. carambola L. leaves, whereas luteolin 6-C-α-L-rhamnopyranosyl-(1-2)-β-D-fucopyranoside (2), apigenin 6-C-β-D-galactopyranoside (3), and apigenin 6-C-α-L-rhamnopyranosyl-(1-2)-β-L-fucopyranoside (4) are isolated for the first time from Family. Oxalidaceae. In vitro α-glucosidase inhibitory activity revealed the potential efficacy of flavone glycosides, viz., 1, 2, 3, and 4 as antidiabetic agents. In contrast, dihydrochalcone glycosides (5–11) showed weak activity, except for compound 12, which showed relatively strong activity.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Anti-Obesity Evaluation of Averrhoa carambola L. Leaves and Assessment of Its Polyphenols as Potential α-Glucosidase Inhibitors

et al. 2022

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“…The optimized structures of potent derivatives were docked into the selective pocket of the α-glucosidase enzyme (N-terminal maltase glucoamylase (PDB ID: 2QMJ)) [16,61], and it was observed that most of the derivatives showed good docking scores and binding interactions with the selective residues (Asp327, Asp203, Arg526, Asp542, His600) (Table 1, Figure 2). The ligands 12a, 12c, 12g, 12i and 12k, having docking scores from −12.50 to −13.30 Kcal/mol with the RMSD values less than 2 Å, were ranked as the most effective α-glucosidase inhibitors.…”

Section: α-Glucosidase (Molecular Docking)mentioning

confidence: 99%

Identification of Cyclic Sulfonamides with an N-Arylacetamide Group as α-Glucosidase and α-Amylase Inhibitors: Biological Evaluation and Molecular Modeling

et al. 2022

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Diabetes mellitus (DM), a complicated metabolic disorder, is due to insensitivity to insulin function or reduction in insulin secretion, which results in postprandial hyperglycemia. α-Glucosidase inhibitors (AGIs) and α-amylase inhibitors (AAIs) block the function of digestive enzymes, which delays the carbohydrate hydrolysis process and ultimately helps to control the postprandial hyperglycemia. Diversified 2-(3-(3-methoxybenzoyl)-4-hydroxy-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl)-N-arylacetamides were synthesized and evaluated for their in vitro inhibitory potential against α-glucosidase and α-amylase enzymes. The compounds with chloro, bromo and methyl substituents demonstrated good inhibition of α-glucosidase enzymes having IC50 values in the range of 25.88–46.25 μM, which are less than the standard drug, acarbose (IC50 = 58.8 μM). Similarly, some derivatives having chloro, bromo and nitro substituents were observed potent inhibitors of α-amylase enzyme, with IC50 values of 7.52 to 15.06 μM, lower than acarbose (IC50 = 17.0 μM). In addition, the most potent compound, N-(4-bromophenyl)-2-(4-hydroxy-3-(3-methoxybenzoyl)-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl)acetamide (12i), was found to be a non-competitive and competitive inhibitor of α-glucosidase and α-amylase enzymes, respectively, during kinetic studies. The molecular docking studies provided the binding modes of active compounds and the molecular dynamics simulation studies of compound 12i in complex with α-amylase also showed that the compound is binding in a fashion similar to that predicted by molecular docking studies.

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“…Due to the special and interesting properties of elemental sulfur, they play a particularly pivotal role in natural products, agrochemicals, and pharmaceuticals. 1–7 In contrast with the carbonyl group, 8,9 the π bond inside CS exhibits good reactivity, which results from the poor orbital overlap between carbon and sulfur owing to their distinctly different size. 10 Thionoesters are regarded as synthetic isosteres of esters 11–13 and have been readily employed as precursors to construct diverse organic compounds.…”

Section: Introductionmentioning

confidence: 99%

An efficient and straightforward approach for accessing thionoesters via palladium-catalyzed C–N cleavage of thioamides

Liu

Irfan

et al. 2022

Org. Biomol. Chem.

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Synthesis of novel 5-(2,5-bis(2,2,2-trifluoroethoxy)phenyl)-1,3,4-oxadiazole-2-thiol derivatives as potential glucosidase inhibitors

Cited by 34 publications

References 55 publications

Anti-Obesity Evaluation of Averrhoa carambola L. Leaves and Assessment of Its Polyphenols as Potential α-Glucosidase Inhibitors

Anti-Obesity Evaluation of Averrhoa carambola L. Leaves and Assessment of Its Polyphenols as Potential α-Glucosidase Inhibitors

Identification of Cyclic Sulfonamides with an N-Arylacetamide Group as α-Glucosidase and α-Amylase Inhibitors: Biological Evaluation and Molecular Modeling

An efficient and straightforward approach for accessing thionoesters via palladium-catalyzed C–N cleavage of thioamides

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