New phthalimide-benzamide-1,2,3-triazole hybrids; design, synthesis, α-glucosidase inhibition assay, and docking study

Sadat-Ebrahimi, Seyed Esmaeil; Rahmani, Abbas; Mohammadi‐Khanaposhtani, Maryam; jafari, Negar; Mojtabavi, Somayeh; Faramarzi, Mohammad Ali; Emadi, Mehdi; Yahya-Meymandi, Azadeh; Larijani, Bagher; Biglar, Mahmoud; Mahdavi, Mohammad

doi:10.1007/s00044-020-02522-7

Cited by 15 publications

(7 citation statements)

References 20 publications

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“…In this study, we established some novel structures to discover lead prospects for further sophisticated studies in the field, as a continuation of our attempts to build newer α‐glucosidase inhibitors via molecular hybridization and to broaden the chemical domain. [ 98–100 ] Apart from that, a recent study has demonstrated that various pyrazole derivatives display antidiabetic activity [ 101–103 ] and hypoglycemic properties. [ 104,105 ] We were motivated to continue research on pyrazole scaffolds by the above‐mentioned essential ways, as well as the important physiological stability and therapeutical efficacy of pyrazole analogs as antidiabetic medicines, as well as the FDA approval of “teneligliptin,” a pyrazole motif‐containing antidiabetic medicine.…”

Section: Future Perspectivementioning

confidence: 99%

Pyrazole scaffold‐based derivatives: A glimpse of α‐glucosidase inhibitory activity, SAR, and route of synthesis

Firdaus

Siddiqui

Alam

et al. 2023

Archiv der Pharmazie

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The α-glucosidase is a validated target to develop drugs for treating type 2 diabetes mellitus. The existing α-glucosidase inhibitors have certain shortcomings related to side effects and route of synthesis. Accordingly, it is inevitable to develop new chemical templates as α-glucosidase inhibitors. Pyrazole derivatives have a special place in medicinal chemistry because of various biological activities. Recently, pyrazole-based heterocyclic compounds have emerged as a promising scaffold to develop α-glucosidase inhibitors. This study focuses on the recently reported pyrazole-based α-glucosidase inhibitors, including their biological activity (in vivo, in vitro, and in silico), structure-activity relationship, and ways of synthesis. The literature revealed the development of several promising pyrazole-based α-glucosidase inhibitors and new synthetic routes for their preparation. The encouraging α-glucosidase inhibitory results of the pyrazole-based heterocyclic compounds make them an attractive target for further research. The authors also foresee the arrival of the pyrazole-based α-glucosidase inhibitors in clinical practice.

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Section: Future Perspectivementioning

confidence: 99%

Pyrazole scaffold‐based derivatives: A glimpse of α‐glucosidase inhibitory activity, SAR, and route of synthesis

Firdaus

Siddiqui

Alam

et al. 2023

Archiv der Pharmazie

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“…Thus, we used in silico approaches to predict the pharmacokinetics and the toxicological potential of 101 phthalimide-1,2,3-triazole derivatives, aiming to identify leader compounds against SARS-CoV-2 ( Figure 1 ). These compounds were categorized according to the radicals attached to the 1,2,3-triazole-phthalimide nucleus into groups A-H, as showed in supplementary material ( Tables S1–S8 ): ( A ) derivatives containing benzyl substituents (Tehrani et al, 2019 ); ( B ) derivatives containing phenyl or benzothiazole groups (Da Silva et al, 2019); ( C ) derivatives containing carbohydrate groups and an additional phthalimide (Assis et al, 2012 ); ( D ) compounds with N -phenylacetamides substituents (Phatak et al, 2019 ); ( E ) presence of benzimidazole group between phtalimide-triazole nucleus and three radicals variations (Singh et al, 2020 ); ( F ) thalidomide derivative analogues (Ronnebaum & Luzzio, 2016 ); ( G ) derivatives of phthalimide-benzamide-1,2,3-triazole (Sadat-Ebrahimi et al, 2020 ); and ( H ) derivatives with an additional phthalimide (López-González et al, 2016 ).…”

Section: Resultsmentioning

confidence: 99%

“…; (B) derivatives containing phenyl or benzothiazole groups(Da Silva et al, 2019); (C) derivatives containing carbohydrate groups and an additional phthalimide(Assis et al, 2012); (D) compounds with N-phenylacetamides substituents(Phatak et al, 2019); (E) presence of benzimidazole group between phtalimide-triazole nucleus and three radicals variations(Singh et al, 2020); (F) thalidomide derivative analogues(Ronnebaum & Luzzio, 2016); (G) derivatives of phthalimide-benzamide-1,2,3-triazole(Sadat- Ebrahimi et al, 2020); and (H) derivatives with an additional phthalimide(L opez-Gonz alez et al, 2016).…”

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confidence: 99%

Identification of 1,2,3-triazole-phthalimide derivatives as potential drugs against COVID-19: a virtual screening, docking and molecular dynamic study

Holanda

Lima

Silva

et al. 2021

Journal of Biomolecular Structure and Dynamics

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In this work we aimed to perform an in silico predictive screening, docking and molecular dynamic study to identify 1,2,3-triazole-phthalimide derivatives as drug candidates against SARS-CoV-2. The in silico prediction of pharmacokinetic and toxicological properties of hundred one 1,2,3-triazole-phtalimide derivatives, obtained from SciFinderV R library, were investigated. Compounds that did not show good gastrointestinal absorption, violated the Lipinski's rules, proved to be positive for the AMES test, and showed to be hepatotoxic or immunotoxic in our ADMET analysis, were filtered out of our study. The hit compounds were further subjected to molecular docking on SARS-CoV-2 target proteins. The ADMET analysis revealed that 43 derivatives violated the Lipinski's rules and 51 other compounds showed to be positive for the toxicity test. Seven 1,2,3-triazole-phthalimide derivatives (A7, A8, B05, E35, E38, E39, and E40) were selected for molecular docking and MFCC-ab initio analysis. The results of molecular docking pointed the derivative E40 as a promising compound interacting with multiple target proteins of SARS-CoV-2. The complex E40-M pro was found to have minimum binding energy of À10.26 kcal/mol and a general energy balance, calculated by the quantum mechanical analysis, of À8.63 eV. MD simulation and MMGBSA calculations confirmed that the derivatives E38 and E40 have high binding energies of À63.47 ± 3 and À63.31 ± 7 kcal/mol against SARS-CoV-2 main protease. In addition, the derivative E40 exhibited excellent interaction values and inhibitory potential against SAR-Cov-2 main protease and viral nucleocapsid proteins, suggesting this derivative as a potent antiviral for the treatment and/or prophylaxis of COVID-19.

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“…34 Then, derivatives 5a-c were synthesized with three ortho, meta, and para substituted azido-benzaldehydes 4a-c via 1,3-dipolar cycloaddition in high yields and purity, using CuSO 4 ⋅5H 2 O and sodium ascorbate as catalysts at room temperature. 35 In the following, a series of α-aminonitriles were produced by adopting three-component Strecker reaction in the presence of various amines, potassium cyanide, and compounds 5a-c as the aldehyde source. 36 Reagents and conditions: a) succinic anhydride, DMAP, CHCl To synthesize a diverse range of products, three different azido benzaldehydes, i.e., 4a-b were employed.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis of novel menthol derivatives containing 1,2,3-triazole group and their in vitro antibacterial activities

Karbasi

Salehi

Aliahmadi

et al. 2023

JSCS

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New N-substituted ?-aminonitrile derivatives from menthol were synthesized by consecutive succinic ester formation, propargylation, 1,3-dipolar Huisgen cycloaddition and Strecker reaction. The structures of the synthesized compounds were confirmed by diverse spectroscopic techniques including 1HNMR, 13C-NMR, ESI-MS, and IR. The novel synthesized compounds were evaluated for their in vitro antibacterial activities against Staphylococcus aureus as Gram-positive and Escherichia coli as Gram-negative bacteria. These compounds demonstrated a strong inhibitory effect against S. aureus with the minimum inhibitory concentration (MIC) values ranged from 32-128 ?g mL-1. Derivatives 6a2, 6b1, 6b4, and 6b5 with a MIC value of 32 ?g mL-1 exhibited the best inhibitory effects.

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New phthalimide-benzamide-1,2,3-triazole hybrids; design, synthesis, α-glucosidase inhibition assay, and docking study

Cited by 15 publications

References 20 publications

Pyrazole scaffold‐based derivatives: A glimpse of α‐glucosidase inhibitory activity, SAR, and route of synthesis

Pyrazole scaffold‐based derivatives: A glimpse of α‐glucosidase inhibitory activity, SAR, and route of synthesis

Identification of 1,2,3-triazole-phthalimide derivatives as potential drugs against COVID-19: a virtual screening, docking and molecular dynamic study

Synthesis of novel menthol derivatives containing 1,2,3-triazole group and their in vitro antibacterial activities

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