Design, synthesis, α-glucosidase inhibitory activity, molecular docking and QSAR studies of benzimidazole derivatives

Dinparast, Leila; Valizadeh, Hassan; Bahadori, Mir Babak; Soltani, Somaieh; Asghari, Behvar; Rashidi, Mohammad‐Reza

doi:10.1016/j.molstruc.2016.02.005

Cited by 46 publications

(19 citation statements)

References 48 publications

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“…The spectral data of all the products are in accordance with the literature [16][17][18][19][20][21][22] values. A plausible reaction mechanism for the domino annulation of ortho-phenylenediamine with β-oxodithioester is shown in Scheme 2.…”

Section: Resultssupporting

confidence: 83%

“…13 Owing to the vast importance of benzimidazoles in drug discovery and other fields, enormous efforts have been made to develop the operationally simple and efficient synthetic methods for their construction. [14][15][16][17][18][19][20][21][22] Classical approaches to benzimidazoles derivatives involve coupling of 1,2-phenylenediamines with aldehydes/carboxylic acids/nitriles/ortho-esters and their derivatives under varying conditions. 23 …”

Section: Introductionmentioning

confidence: 99%

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Brønsted acid-catalyzed metal-free one-pot synthesis of benzimidazoles via [4+1] heteroannulation of ortho-phenylenediamines with β-oxodithioesters

Srivastava¹,

Shukla²,

Yadav³

et al. 2017

Arkivoc

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An operationally simple and user-friendly one-pot domino protocol for the synthesis of 2-aryl/hetaryl benzimidazoles has been devised from easily available and inexpensive 1,2-phenylenediamines and β-oxodithioesters. The strategic [4+1] heteroannulation initiated by Brønsted acid PTSA relies on remarkable domino sequence of condensation, cyclization, and elimination. The current approach enables N-H/N-H functionalization under solventless and metal-free conditions leading to diverse benzimidazoles. The reactions proceeded smoothly affording the desired products in good to excellent yields, exhibiting gram-scale ability and broad functional groups tolerance. Notably, the approach is highly chemo-and regioselective.

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Section: Resultssupporting

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Brønsted acid-catalyzed metal-free one-pot synthesis of benzimidazoles via [4+1] heteroannulation of ortho-phenylenediamines with β-oxodithioesters

Srivastava¹,

Shukla²,

Yadav³

et al. 2017

Arkivoc

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“…Benzimidazole derived compounds are class of N‐comprising heterocyclic motifs widely used in organic and medicinal chemistry as imperative pharmacophore exhibiting various biological activities . These compounds are bicyclic in nature which consists of the fusion of benzene .…”

Section: Introductionmentioning

confidence: 99%

“…Recently, benzimidazole and its derivatives have attained considerable attention due to their potential applications as antiulcer (omeprazole), tubulin polymerization inhibitor, antihypertensive, antifungal, anticancer, anthelmintic, antibacterial, cytotoxicity, antimicrobial, anti‐inflammatory, antitumor, Trypanosomacruzi (Tc) infection, histamine‐H3 antagonist, antioxidant, gastro protective and anti‐parasitic, DNA binding and DNA‐encoded library (DEL) technology, enzyme inhibition, Alzheimer disease (AD) and HIV‐1 induced inhibitor for cytopathic activity. Furthermore, these derivatives have been employed as organic ligands, corrosion science, functional materials, catalysis, chemosensing, fluorescence signaling, self‐aggregation and dye sensitized solar cells (DSSCs) …”

Section: Introductionmentioning

confidence: 99%

Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole‐based hydrazones: A synergistic experimental‐computational analysis

Rafiq

Khalid

Tahir

et al. 2019

Applied Organom Chemis

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Present study advocates the joint experimental and computational studies of two potent benzoimidazole-based hydrazones with chemical formula C 23 H 18 F 2 N 4 O (5a) and C 25 H 22 FN 5 O 3 (5b). Both 5a and 5b were synthesized and resolved into their crystal structures using SC-XRD for the assessment of bond lengths, bond angles, unit cells and space groups. The structures of 5a and 5b were chemically characterized using infrared (FT-IR), UV-Visible, nuclear magnetic resonance ( 1 H-NMR and 13 C-NMR), EIMS and elemental analysis. DFT at M06-2X/6-31G(d,p) level of theory was performed to get optimized structures and countercheck the experimental findings. Overall, DFT findings show excellent concurrence with the experimental data which confirms the purity of both compounds. FMO, NBO analysis, MEP surfaces and nonlinear optical (NLO) properties were explored at same level of theory. UV-Vis analysis at TDDFT/M06-2X/6-31G(d,p) level of theory showed that 5b is red shifted with λ max 331.69 nm as compared to 5a with λ max 240.25 nm. Global reactivity parameters were estimated using energy of FMOs indicated the greater harness value than the softness values of 5a and 5b. NBO analysis confirmed that the presence of non-covalent interactions, hydrogen bonding and hyper conjugative interactions are pivotal cause for the existence of 5a and 5b in the solid-state. NLO results of 5a and 5b were observed better than standard molecule recommended the NLO activity of said molecules for optoelectronic applications. Highlights• Two novel benzoimidazole-based hydrazones were synthesized.• XRD, NMR, FT-IR, UV-Vis, EIMS and elemental analysis were performed for the characterization.

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“…Benzimidazole has structural similarity to purine, and its analogs could compete with purines [6]. Many benzimidazolescontaining drugs such as thiabendazole (antiparasitic), norastemizole (antihistaminic), telmisartan (antihypertensive) and omeprazole (antiulcer) are used widely to treat the said ailments [7,8].…”

Section: Introductionmentioning

confidence: 99%

Antidepressant, Analgesic Activity and SAR Studies of Substituted Benzimidazoles

Siddiqui¹,

Alam²,

Sahu³

et al. 2016

Asian Jour. Pharmac. Rese.

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ABSTRACT:Purpose. Benzimidazole class of compound is found to have diverse biological properties. From the literature study, it is observed that depression is a severe mental disease affecting a huge population and pain is affecting about 20% of world population. In continuation of our previous research work, we selected benzimidazole pharmacophore to further explore its pharmacological activities. Methods. Forced swim test and Thermal stimulus test were used to assess the antidepressant and analgesic activity of synthesized benzimidazole analogs. Results. The antidepressant activity results showed that compound 3j was found most potent having Mean ± SEM value 21.6 ± 0.8 for treated group. Furthermore, in the analgesic test, 3b, 3j, and 3o showed Mean ± SEM values; 1.8 ± 0.10, 2.3 ± 0.10 and 2.2 ± 0.10, respectively. The study results suggested that these compounds could be explored further for the development of better antidepressant and analgesic agents. Conclusion. From the present study, it may be concluded that these active benzimidazole derivatives have been found to possess potential antidepressant and analgesic activity.

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Design, synthesis, α-glucosidase inhibitory activity, molecular docking and QSAR studies of benzimidazole derivatives

Cited by 46 publications

References 48 publications

Brønsted acid-catalyzed metal-free one-pot synthesis of benzimidazoles via [4+1] heteroannulation of ortho-phenylenediamines with β-oxodithioesters

Brønsted acid-catalyzed metal-free one-pot synthesis of benzimidazoles via [4+1] heteroannulation of ortho-phenylenediamines with β-oxodithioesters

Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole‐based hydrazones: A synergistic experimental‐computational analysis

Antidepressant, Analgesic Activity and SAR Studies of Substituted Benzimidazoles

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