Synthesis, molecular modeling and evaluation of α-glucosidase inhibition activity of 3,4-dihydroxy piperidines

Kasturi, Siva Prasad; Surarapu, Sujatha; Srinivas, U.; Dwivedi, Shubham; Yogeeswari, Perumal; Sigalapalli, Dilep Kumar; Babu, Bathini Nagendra; Ethiraj, K. S.; Anireddy, Jaya Shree

doi:10.1016/j.ejmech.2018.02.072

Cited by 29 publications

(8 citation statements)

References 41 publications

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“…[90,91] Diabetes mellitus (DM) is a metabolic sickness described by elongated hyperglycemia, which can lead to a high threat of carcinoma, nephropathy, heart disease, retinopathy, and metabolic disorders. [92][93][94][95] WHO reported that about 420 million population is suffering from diabetes, and the cases would rise to 642 million by 2040. [96,97] According to reports, about 90% of cases of diabetes are Type 2 diabetes (T2D) which can be referred to as Noninsulin-dependent diabetes mellitus.…”

Section: Development Of Antimalarial and Antidiabetic Agents Using Cà...mentioning

confidence: 99%

C−H Functionalized Molecules: Synthesis, Reaction Mechanism, and Biological Activity

et al. 2023

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Replacement of traditionally unreactive CÀ H bond with CÀ C or CÀ X (X=Hetero atom) has emerged as one of the widely accepted methods over the last few decades for the synthesis of complex organic molecules which can act as important intermediates for the synthesis of biologically active compounds. Selective functionalization of the CÀ H bond especially in the presence of a more reactive CÀ H bond has remained one of the biggest challenges for synthetic organic chemists. The hybridization state of the CÀ H bond, substitution pattern, and presence of directive groups are some of the factors which have been exploited by researchers over the years for achieving fruitful results. A considerable amount of work has been reported in the literature on the use of metal catalysts for CÀ H bond functionalization leading to the formation of a CÀ M (carbon-metal) bond which is also known as CÀ H bond activation. This review aims to summarize various synthetic strategies reported for the CÀ H functionalization, which has led to the development of targeted complex molecules with medicinal properties.

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Section: Development Of Antimalarial and Antidiabetic Agents Using Cà...mentioning

confidence: 99%

C−H Functionalized Molecules: Synthesis, Reaction Mechanism, and Biological Activity

et al. 2023

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“…In diabetes mellitus, the pancreas prepares insulin but body cells do not recognize it. As a result, food intake causes hyperglycemia and body cells suffer glucose deficiency [ 4 ]. Early symptoms of diabetes are excessive thirst, nausea, shortness of breath, fatigue and frequent urination, but unattended prolonged hyperglycemia can cause other aberrations, including leg amputation, blindness, nerve damage, kidney failure and cardiovascular complications [ 1 , 5 ].…”

Section: Introductionmentioning

confidence: 99%

Experimental and Computational Analysis of Newly Synthesized Benzotriazinone Sulfonamides as Alpha-Glucosidase Inhibitors

et al. 2022

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Diabetes mellitus is a chronic metabolic disorder in which the pancreas secretes insulin but the body cells do not recognize it. As a result, carbohydrate metabolism causes hyperglycemia, which may be fatal for various organs. This disease is increasing day by day and it is prevalent among people of all ages, including young adults and children. Acarbose and miglitol are famous alpha-glucosidase inhibitors but they complicate patients with the problems of flatulence, pain, bloating, diarrhea, and loss of appetite. To overcome these challenges, it is crucial to discover new anti-diabetic drugs with minimal side effects. For this purpose, benzotriazinone sulfonamides were synthesized and their structures were characterized by FT-IR, 1H-NMR and 13C-NMR spectroscopy. In vitro alpha-glucosidase inhibition studies of all synthesized hybrids were conducted using the spectrophotometric method. The synthesized compounds revealed moderate-to-good inhibition activity; in particular, nitro derivatives 12e and 12f were found to be the most effective inhibitors against this enzyme, with IC50 values of 32.37 ± 0.15 µM and 37.75 ± 0.11 µM. In silico studies, including molecular docking as well as DFT analysis, also strengthened the experimental findings. Both leading compounds 12e and 12f showed strong hydrogen bonding interactions within the enzyme cavity. DFT studies also reinforced the strong binding interactions of these derivatives with biological molecules due to their lowest chemical hardness values and lowest orbital energy gap values.

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“…Some commercially available α-glucosidase inhibitors, including miglitol, voglibose, and acarbose, have been used in the clinical treatment of T2DM, but they still show several adverse effects ( Chai et al, 2015 ; Khursheed et al, 2019 ; Rocha et al, 2019 ). In addition, α-glucosidase is closely related to hepatitis, cancer, and Pompe disease ( Kasturi et al, 2018 ; Gulcin et al, 2019 ). Therefore, it is always beneficial in medicinal chemistry to develop potent α-glucosidase inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Coumarin-Chalcone Derivatives as α-Glucosidase Inhibitors

Luo

Wang

et al. 2022

Front. Chem.

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Coumarin and chalcone, two important kinds of natural product skeletons, both exhibit α-glucosidase inhibitory activity. In this work, coumarin-chalcone derivatives 3 (a∼v) were synthesized, and their α-glucosidase inhibitory activity was screened. The results showed that all synthetic derivatives (IC50: 24.09 ± 2.36 to 125.26 ± 1.18 μM) presented better α-glucosidase inhibitory activity than the parent compounds 3-acetylcoumarin (IC50: 1.5 × 105 μM) and the positive control acarbose (IC50: 259.90 ± 1.06 μM). Among them, compound 3t displayed the highest α-glucosidase inhibitory activity (IC50: 24.09 ± 2.36 μM), which was approximately 10 times stronger than that of acarbose. The kinetic assay of 3t (KI = 18.82 μM, KIS = 59.99 μM) revealed that these compounds inhibited α-glucosidase in a mixed-type manner. Molecular docking was used to simulate the interaction between α-glucosidase and compound 3t.

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Synthesis, molecular modeling and evaluation of α-glucosidase inhibition activity of 3,4-dihydroxy piperidines

Cited by 29 publications

References 41 publications

C−H Functionalized Molecules: Synthesis, Reaction Mechanism, and Biological Activity

C−H Functionalized Molecules: Synthesis, Reaction Mechanism, and Biological Activity

Experimental and Computational Analysis of Newly Synthesized Benzotriazinone Sulfonamides as Alpha-Glucosidase Inhibitors

Synthesis and Evaluation of Coumarin-Chalcone Derivatives as α-Glucosidase Inhibitors

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