Synthesis, antimicrobial and α-glucosidase inhibition of new benzimidazole-1,2,3-triazole-indoline derivatives: a combined experimental and computational venture

Deswal, Laxmi; Verma, Vikas; Kumar, Devinder; Deswal, Yogesh; Kumar, Ashwani; Kumar, Rajnish; Parshad, Mahavir; Bhatia, Meenakshi

doi:10.1007/s11696-022-02436-1

Cited by 18 publications

(7 citation statements)

References 39 publications

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“…The third stage corresponds to the loss of C 7 H 4 N 4 S fragment (observed mass loss = 42.83%, calculated = 42.80%). The same behavior was observed for the zinc complex (5). Complex decomposes in 100-690 C temperature range, leaving ZnO as the residue.…”

Section: Thermal Studiessupporting

confidence: 74%

“…The 13 C NMR spectra of the ligand (1) and its zinc(II) complex (5) were recorded in DMSO-d 6 solution at 300 K (Figures S7 and S9 of supplementary). In the spectrum of ligand, azomethine carbon atom resonates at δ 155.1 ppm, while in the spectrum of complex it undergoes downfield shifting up to δ 157.6 ppm, thereby implying the coordination through lone pair electrons of nitrogen to the metal atom.…”

Section: C Nmr Spectramentioning

confidence: 99%

“…[4] Hyperglycaemia is usually associated with symptoms such as fatigue, thirst, frequent urination, recurring infections, blurred vision, and dysfunction of a variety of organs including the kidneys, blood vessels, heart, and nerves. [5,6] Diabetes is primarily classified into two types; Type-I and Type-II. [7] Type-II diabetes is the most frequent form of DM, accounting for 95% of total diabetes cases.…”

Section: Introductionmentioning

confidence: 99%

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Instigating the in vitro antidiabetic activity of new tridentate Schiff base ligand appended M(II) complexes: From synthesis, structural characterization, quantum computational calculations to molecular docking, and molecular dynamics simulation studies

Deswal

Asija

Tufail³

et al. 2023

Applied Organom Chemis

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In search of novel medications that could be effective in preventing and treating diabetes, four new [Co(L)(H 2 O) 3 ] (2), [Ni(L)(H 2 O) 3 ] (3), [Cu(L)(H 2 O)] (4) and [Zn(L)(H 2 O)] (5) complexes were synthesized from 4-Chloro-2-(((3-mercapto-5-[pyridin-4-yl]-4H-1,2,4-triazol-4-yl)imino)methyl)phenol ligand (H 2 L),which is obtained by the condensation of 5-chlorosalicylaldehyde with 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol in 1:1 ratio. The Fouriertransform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR)( 1 H and 13 C), elemental analyses, UV-visible, electron spin resonance (ESR), thermogravimetric analysis (TGA), scanning electron microscopy, energy dispersive X-ray analysis (EDAX), and X-ray diffraction (XRD) studies were used to successfully characterize the compounds. The ligand act in a tridentate manner and coordinates to the metal ions through N azomethine , O phenolic and S thiol functionalities. On the premise of their spectral and physico-analytical data; octahedral geometry for complex 2 and 3, while square planar and tetrahedral geometry for complex 4 and 5 was proposed. Theoretical calculations of the synthesized compounds have been performed by using density functional theory (DFT)/B3LYP method and parameters such as HOMO-LUMO energy values and MESP were calculated. In vitro examinations against α-amylase and α-glucosidase reveal promising results for the compounds. Nickel (II) complex(3) against α-amylase and zinc (II) complex (5) against α-glucosidase were found to be good inhibitors. Molecular docking experiments against the receptors 1BSI and 5ZCC were done to support the observation and considerable

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Section: Thermal Studiessupporting

confidence: 74%

Section: C Nmr Spectramentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Instigating the in vitro antidiabetic activity of new tridentate Schiff base ligand appended M(II) complexes: From synthesis, structural characterization, quantum computational calculations to molecular docking, and molecular dynamics simulation studies

Deswal

Asija

Tufail³

et al. 2023

Applied Organom Chemis

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“…Potato dextrose broth and nutrient broth were utilized as the growth media for fungal and bacterial species, respectively. Initially, the stock solutions of synthesized compounds with a concentration of 100 µg/mL were prepared in dimethylsulphoxide, and the solutions were again serially diluted to obtain concentrations of 50, 25, 12.5, 6.25, 3.12, 1.56 µg/mL [ 35 ]. 1 mL of the above prepared solutions was poured into each test tube containing 1 mL of nutrient broth and potato dextrose broth for antibacterial and antifungal activity, respectively.…”

Section: Methodsmentioning

confidence: 99%

Development of new tridentate ligands bearing hydrazone motif and their diorganotin(IV) complexes: Synthesis, spectral, antimicrobial and molecular docking studies

et al. 2022

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Current antimicrobial drug discovery and advancement attempts are aimed to identify new complexes that can work effectively against the infections caused by microbes. The aim of present study was to synthesize new diorganotin(IV) complexes of N' -((8-hydroxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)methylene)-2-nitrobenzohydrazide (H 2 L 1 ), N' -((8-hydroxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)methylene)-3-methoxybenzohydrazide (H 2 L 2 ) and N' -((8-hydroxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)methylene)-4-methylbenzohydrazide (H 2 L 3 ) Schiff base ligands with formula R 2 SnL 1−3 (where R = Me, Et, Bu and Ph). Various spectral and physico-analytical techniques such as elemental analysis, FT-IR, multinuclear ( 1 H, 13 C, 119 Sn) NMR, HRMS and XRD were utilized to structurally elucidate the prepared compounds. Based on the spectral data, it was concluded that ligands behave in a tridentate manner and coordinates to the central tin atom through ONO donor atoms. Furthermore, the synthesized compounds were examined for in vitro antimicrobial activity against four bacterial and two fungal strains. Among the examined compounds, Ph 2 SnL 1 complex (MIC = 0.0095 µmol/mL) was found to be the most active. To rationalize the preferred mode of interactions of the most active compound, a molecular docking study of compound Ph 2 SnL 1 was executed in the binding site of 3-oxoacyl-[acyl-carrier-protein] synthase 2 (FabF) of E. coli and sterol 14-alpha demethylase of C. albicans . Compound Ph 2 SnL 1 inhibits the microbes effectively and it could be an effective and new candidate for the modulation of various infections. Graphical Abstract New diorganotin(IV) complexes ( 4–15 ) were prepared from tridentate Schiff base hydrazones ( 1–3 ). The compounds were examined for in vitro antimicrobial activity. Further, molecular docking study of the most potent compound Ph 2 SnL 1 ( 7 ) was performed against the enzyme 3-oxoacyl-[acyl-carrier-protein] synthase 2 (FabF) of E. coli and sterol 14-alpha demethylase of C. albicans . Supplementary Information The online version contains supplementary material avail...

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“…Many of the prepared derivatives have efficacy comparable or superior to the standard drugs used for the same purpose. [138][139][140][141][142][143][144][145][146][147][148][149][150][151][152][153]…”

Section: Review Synopenmentioning

confidence: 99%

A Review on Benzimidazole Heterocyclic Compounds: Synthesis and Their Medicinal Activity Applications

Alheety,

Mohammed,

Farhan

et al. 2023

SynOpen

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Benzimidazole is a heterocyclic compound formed by fusing the benzene ring with an imidazole ring that contains two nitrogen atoms. Benzimidazole and its derivatives are prepared in different ways, including condensation of o-phenylenediamine with carbonyl compounds (aldehydes and ketones) or with carboxylic acids and their derivatives. The benzimidazoles can also be prepared by rearranging other heterocyclic compounds such as quinoxaline derivatives, triazole derivatives, etc. In recent decades, benzimidazoles were prepared using green methods such as microwaves, ultrasound, and the use of an environmentally friendly catalyst, as well as photochemical reactions. Benzimidazoles have attracted the interest of scientists and researchers due to the great medical efficacy shown by them for various diseases. The benzimidazole derivatives show many pharmacological activities such as anticancer, anti-inflammatory, antioxidant, anticoagulant, antiviral, etc. This review focuses on shedding light on benzimidazole and its derivatives, the most important methods used to prepare it, as well as the biological applications in our daily lives.

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Synthesis, antimicrobial and α-glucosidase inhibition of new benzimidazole-1,2,3-triazole-indoline derivatives: a combined experimental and computational venture

Cited by 18 publications

References 39 publications

Instigating the in vitro antidiabetic activity of new tridentate Schiff base ligand appended M(II) complexes: From synthesis, structural characterization, quantum computational calculations to molecular docking, and molecular dynamics simulation studies

Instigating the in vitro antidiabetic activity of new tridentate Schiff base ligand appended M(II) complexes: From synthesis, structural characterization, quantum computational calculations to molecular docking, and molecular dynamics simulation studies

Development of new tridentate ligands bearing hydrazone motif and their diorganotin(IV) complexes: Synthesis, spectral, antimicrobial and molecular docking studies

A Review on Benzimidazole Heterocyclic Compounds: Synthesis and Their Medicinal Activity Applications

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