Fe–SBA-15 catalyzed synthesis of 2-alkoxyimidazo[1,2-a]pyridines and screening of their in silico selectivity and binding affinity to biological targets

Payra, Soumen; Saha, Arijit; Wu, Chia-Ming; Selvaratnam, Balaranjan; Dramstad, Thorn; Mahoney, Luther; Verma, Sant Kumar; Thareja, Suresh; Koodali, Ranjit T.; Banerjee, Subhash

doi:10.1039/c6nj02134d

Cited by 21 publications

(12 citation statements)

References 79 publications

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“…During this computational process, the maximum numbers of cavities were set to five, the grid resolution to 0.80 Å, and the probe size to 1.2 Å, while the other parameters were taken as default. 30 The docking scores indicate the significant binding interactions, i.e., hydrogen-bonding and steric interactions that take place between the ligand of different conformations and key amino acid residues in the binding pocket of the target. Furthermore, the Mol Dock score is the sum of internal ligand energies, protein interaction energies, and soft penalties.…”

Section: Methodsmentioning

confidence: 99%

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Molecular Iodine-Catalyzed Synthesis of Imidazo[1,2-a]Pyridines: Screening of Their In Silico Selectivity, Binding Affinity to Biological Targets, and Density Functional Theory Studies Insight

2022

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The present paper discloses an ultrasonication strategy assisted by molecular iodine as an environmentally benign catalyst leading to the synthesis of pharmacologically significant imidazo[1,2- a ]pyridine scaffolds. The molecular-iodine-catalyzed approach for the synthesis of biologically active synthetic equivalents was achieved through three-component coupling embracing 2-aminopyridine derivatives, pertinent acetophenones, and dimedone in water medium under aerobic conditions. The higher product yield (up to 96%) with a miniature reaction time and modest catalyst loading as demonstrated by higher ecological compatibility and sustainability factors are fascinating features of this protocol. The structures of synthesized compounds were accomplished through FT-IR, 1 H NMR, 13 C NMR, mass, and elemental analysis data. The virtual screening of synthetic moieties was performed to ascertain the in silico selectivity and binding affinities against several biological targets. Lipinski’s rules of five, ADMET, and TOPKAT descriptors were used to evaluate the drug-likeness assets. Furthermore, a quantum computational study was computed at the B3LYP/6-311G++(d,p) level of theory to investigate the density functional theory-based chemical reactivity parameters and HOMO–LUMO energy gap of the synthesized derivatives. The present studies open the way for in vitro and in vivo testing of synthesized derivatives as potent inhibitors with an improved pharmacological profile against farnesyl diphosphate synthase, phosphodiesterase III, CXCR4, and GABAa receptor agonists.

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Section: Methodsmentioning

confidence: 99%

“…In general, the rerank score is better than the docking score function for determining the best pose among the various poses derived from the identical ligand. 30 , 31 …”

Section: Methodsmentioning

confidence: 99%

Molecular Iodine-Catalyzed Synthesis of Imidazo[1,2-a]Pyridines: Screening of Their In Silico Selectivity, Binding Affinity to Biological Targets, and Density Functional Theory Studies Insight

2022

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“…The software Molegro also allows the analysis of ligand interactions with protein amino acid residues: hydrogen bonds (blue dashed lines), steric interactions (red dashed lines) [12] and electrostatic interactions (green dashed lines) [13]. Therefore, the types of interactions of 5 poses for each protein were obtained.…”

Section: Methodsmentioning

confidence: 99%

In silico study of various compounds from essential oil of Cymbopogon winterianus against Pseudomonas aeruginosa targets

Moura

Monteiro

Maia

et al. 2019

Proceedings of MOL2NET 2019, International Conference on Multidisciplinary Sciences, 5th Edition

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Graphical Abstract AbstractPseudomonas aeruginosa is a gramnegative bacterium that can be found in soil, aquatic environments or on the surface of animals, plants and humans [1]. It is commonly isolated in immunocompromised patients in intensive care units and can cause urinary tract infections, pneumonia, folliculitis, otitis, keratitis, osteomyelitis and meningitis [2,3]. The compounds present in oils of species of the genus Cymbopogon are known to present several activities, including antimicrobial activity [4]. This work aims to perform a multitarget molecular modeling of essential oil components from citronella (Cymbopogon winterianus) against P. aeruginosa.

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“…The regioselective synthesis of novel 2-alkoxyimidazopyridine derivatives 305 via an one-pot three-component reaction of 2-AP, nitrostyrene 303 and alcohol 304 using Fe-SBA-15 as a catalyst was reported by Payra et al (Scheme 101) [175]. Various iron catalysts viz., FeCl 3 , FeSO 4, and nano-Fe 3 O 4 have been employed for this reaction but they resulted in a poor yield of about 37, 19 and 41%, respectively.…”

Section: Reviewmentioning

confidence: 99%

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

Reen

Kumar

Sharma

2019

Beilstein J. Org. Chem.

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A comprehensive account of recent advances in the synthesis of imidazopyridines, assisted through transition-metal-catalyzed multicomponent reactions, C–H activation/functionalization and coupling reactions are highlighted in this review article. The basic illustration of this review comprises of schemes with concise account of explanatory text. The schemes depict the reaction conditions along with a quick look into the mechanism involved to render a deep understanding of the catalytic role. At some instances optimizations of certain features have been illustrated through tables, i.e., selectivity of catalyst, loading of the catalyst and percentage yield with different substrates. Each of the reported examples has been rigorously analyzed for reacting substrates, reaction conditions and transition metals used as the catalyst. This review will be helpful to the chemists in understanding the challenges associated with the reported methods as well as the future possibilities, both in the choice of substrates and catalysts. This review would be quite appealing to a wider range of organic chemists in academia and industrial R&D sectors working in the field of heterocyclic syntheses. In a nutshell, this review will be a guiding torch to envisage: (i) the role of various transition metals in the domain dedicated towards method development and (ii) for the modifications needed thereof in the R&D sector.

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Fe–SBA-15 catalyzed synthesis of 2-alkoxyimidazo[1,2-a]pyridines and screening of their in silico selectivity and binding affinity to biological targets

Abstract: Regioselective synthesis of 2-alkoxyimidazopyridines by Fe-SBA-15 and screening of their in silico binding affinity to biological targets.

Cited by 21 publications

References 79 publications

Molecular Iodine-Catalyzed Synthesis of Imidazo[1,2-a]Pyridines: Screening of Their In Silico Selectivity, Binding Affinity to Biological Targets, and Density Functional Theory Studies Insight

Molecular Iodine-Catalyzed Synthesis of Imidazo[1,2-a]Pyridines: Screening of Their In Silico Selectivity, Binding Affinity to Biological Targets, and Density Functional Theory Studies Insight

<em>In silico </em>study of various compounds from essential oil of <em>Cymbopogon winterianus</em> against <em>Pseudomonas aeruginosa </em>targets

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

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