Dihydropyridines as potential α-amylase and α-glucosidase inhibitors: Synthesis, in vitro and in silico studies

Yousuf, Hina; Shamim, Shahbaz; Khan, Khalid Mohammed; Chigurupati, Sridevi; Kanwal,; Hameed, Shehryar; Khan, Muhammad Naseem; Taha, Muhammad; Arfeen, Minhajul

doi:10.1016/j.bioorg.2020.103581

Cited by 51 publications

(22 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cytotoxicity evaluations lead us to the conclusion that compound 5e with meta substituted fluoro derivatives having thio linkage possessed the highest IC 50 compared to control, as shown in Figure 10 . All this structure activity relationship provided us with the conclusion that meta substitution of halogenated derivatives with either oxo or thio linkages provided promising results after in vitro analysis [ 16 , 17 , 18 , 19 , 20 ].…”

Section: Resultsmentioning

confidence: 99%

Structure-Based Designing, Solvent Less Synthesis of 1,2,3,4-Tetrahydropyrimidine-5-carboxylate Derivatives: A Combined In Vitro and In Silico Screening Approach

et al. 2021

View full text Add to dashboard Cite

Objective: In this study, small molecules possessing tetrahydropyrimidine derivatives have been synthesized having halogenated benzyl derivatives and carboxylate linkage. As previously reported, FDA approved halogenated pyrimidine derivatives prompted us to synthesize novel compounds in order to evaluate their biological potential. Methodology: Eight pyrimidine derivatives have been synthesized from ethyl acetoacetate, secondary amine, aromatic benzaldehyde by adding catalytic amount of CuCl2·2H2O via solvent less Grindstone multicomponent reagent method. Molecular structure reactivity and virtual screening were performed to check their biological efficacy as an anti-oxidant, anti-cancer and anti-diabetic agent. These studies were supported by in vitro analysis and QSAR studies. Results: After combined experimental and virtual screening 5c, 5g and 5e could serve as lead compounds, having low IC50 and high binding affinity.

show abstract

Section: Resultsmentioning

confidence: 99%

Structure-Based Designing, Solvent Less Synthesis of 1,2,3,4-Tetrahydropyrimidine-5-carboxylate Derivatives: A Combined In Vitro and In Silico Screening Approach

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Molecular docking was conducted to explore the interaction of inhibitors with α-glucosidase and α- amylase using Sybyl (Version 2.1.1, Tripos, US) according to our previous report. 33 The crystal structure of α-glucosidase (PDB: 3AJ7) 33 , 35 and α-amylase (PDB: 3BAJ) 36 , 37 were obtained from the Protein Data Bank. Compounds were prepared with addition of hydrogen atoms, addition of charge with Gasteiger-Hückle mode, and energy minimisation.…”

Section: Methodsmentioning

confidence: 99%

In vitro and in silico studies of bis (indol-3-yl) methane derivatives as potential α-glucosidase and α-amylase inhibitors

Zheng

Xiong

Liao

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

In this paper, bis (indol-3-yl) methanes (BIMs) were synthesised and evaluated for their inhibitory activity against α-glucosidase and α-amylase. All synthesised compounds showed potential α-glucosidase and α-amylase inhibitory activities. Compounds 5 g (IC 50 : 7.54 ± 1.10 μM), 5e (IC 50 : 9.00 ± 0.97 μM), and 5 h (IC 50 : 9.57 ± 0.62 μM) presented strongest inhibitory activities against α-glucosidase, that were ∼ 30 times stronger than acarbose. Compounds 5 g (IC 50 : 32.18 ± 1.66 µM), 5 h (IC 50 : 31.47 ± 1.42 µM), and 5 s (IC 50 : 30.91 ± 0.86 µM) showed strongest inhibitory activities towards α-amylase, ∼ 2.5 times stronger than acarbose. The mechanisms and docking simulation of the compounds were also studied. Compounds 5 g and 5 h exhibited bifunctional inhibitory activity against these two enzymes. Furthermore, compounds showed no toxicity against 3T3-L1 cells and HepG2 cells. Highlights A series of bis (indol-3-yl) methanes (BIMs) were synthesised and evaluated inhibitory activities against α -glucosidase and α-amylase. Compound 5g exhibited promising activity (IC 50 = 7.54 ± 1.10 μM) against α -glucosidase. Compound 5s exhibited promising activity (IC 50 = 30.91 ± 0.86 μM) against α-amylase. In silico studies were performed to confirm the binding interactions of synthetic compounds with the enzyme active site.

show abstract

“…Cyclohexane‐1,3‐diones are key intermediates for the synthesis of several natural products and heterocycles [1–7] . These molecules show diverse kinds of biological activities such as anticancer, [8] antiviral, [9] antioxidant, [10] and are used in different photophysical studies [11–17] .…”

Section: Introductionmentioning

confidence: 99%

“…Cyclohexane-1,3-diones are key intermediates for the synthesis of several natural products and heterocycles. [1][2][3][4][5][6][7] These molecules show diverse kinds of biological activities such as anticancer, [8] antiviral, [9] antioxidant, [10] and are used in different photophysical studies. [11][12][13][14][15][16][17] In addition, these compounds serve as an important substrate for the synthesis of six-membered Nheterocycles for instance 1,4-dihydropyridine, acridine-1,8-diones, benzoacridinones, quinolones, and pyridine derivatives (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

Sharma¹,

Kumar

et al. 2022

ChemistrySelect

View full text Add to dashboard Cite

Cyclohexane‐1,3‐dione and its derivatives are imperative precursors in synthetic organic chemistry as they are useful intermediates for the synthesis of a wide range of biologically active natural products, heterocycles and pharmaceuticals. Recently, cyclohexane‐1,3‐diones have been used for the synthesis of varied array of six‐membered nitrogen‐containing heterocycles in the presence of aldehydes, acetoacetic esters, malononitrile, chalcones, coumarins, acetophenones, amino acids, amines, etc. under catalytic and non‐catalytic conditions. Newest studies on the importance of these heterocycles motivated us to compile all the recently developed processes which include the fabrication of six‐membered nitrogen heterocycles. This article is mainly focused on the efficient synthesis of six‐membered N‐heterocycles i. e. 1,4‐dihydropyridine, acridine‐1,8‐diones, benzoacridinones, quinolones and pyridine derivatives from cyclohexane‐1,3‐diones as one of the substrates, published for the last ten years.

show abstract

Dihydropyridines as potential α-amylase and α-glucosidase inhibitors: Synthesis, in vitro and in silico studies

Cited by 51 publications

References 28 publications

Structure-Based Designing, Solvent Less Synthesis of 1,2,3,4-Tetrahydropyrimidine-5-carboxylate Derivatives: A Combined In Vitro and In Silico Screening Approach

Structure-Based Designing, Solvent Less Synthesis of 1,2,3,4-Tetrahydropyrimidine-5-carboxylate Derivatives: A Combined In Vitro and In Silico Screening Approach

In vitro and in silico studies of bis (indol-3-yl) methane derivatives as potential α-glucosidase and α-amylase inhibitors

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

Contact Info

Product

Resources

About