Effect of the lipophilic parameter (log P) on the anti-parasitic activity of imidazo[1,2-a]pyridine derivatives

López‐Martínez, Margarita; Salgado-Zamora, Héctor; Campos-Aldrete, Ma. Elena; Trujillo‐Ferrara, José G.; Correa‐Basurto, José; Mexica-Ochoa, Carlos

doi:10.1007/s00044-010-9547-3

Cited by 15 publications

(8 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The high affinity of 7 was expected since the carboxylic group is a common feature in classic NSAIDs, whereas the electro‐withdrawing nitro functionality in compound 1 seems a good alternative. The biological activities of the cyclohexyl or aminocyclohexyl functional groups in compound 15 have been previously evaluated as part of other heterocyclic compounds . Thus, it can be concluded that the electro‐withdrawing, acidic, and volumetric functional groups will favor COX‐1/2 binding.…”

Section: Resultsmentioning

confidence: 99%

Profiling the interaction of 1‐phenylbenzimidazoles to cyclooxygenases

Gómez-Castro

López‐Martínez

Hernández-Pineda

et al. 2019

J of Molecular Recognition

View full text Add to dashboard Cite

In the design of 1-phenylbenzimidazoles as model cyclooxygenase (COX) inhibitors, docking to a series of crystallographic COX structures was performed to evaluate their potential for high-affinity binding and to reproduce the interaction profile of well-known COX inhibitors. The effect of ligand-specific induced fit on the calculations was also studied. To quantitatively compare the pattern of interactions of model compounds to the profile of several cocrystallized COX inhibitors, a geometric parameter, denominated ligand-receptor contact distance (LRCD), was developed. The interaction profile of several model complexes showed similarity to the profile of COX complexes with inhibitors such as iodosuprofen, iodoindomethacin, diclofenac, and flurbiprofen. Shaping of high-affinity binding sites upon ligand-specific induced fit mostly determined both the affinity and the binding mode of the ligands in the docking calculations. The results suggest potential of 1-phenylbenzimidazole derivatives as COX inhibitors on the basis of their predicted affinity and interaction profile to COX enzymes. The analyses also provided insights into the role of induced fit in COX enzymes. While inhibitors produce different local structural changes at the COX ligand binding site, induced fit allows inhibitors in diverse chemical classes to share characteristic interaction patterns that ensure key contacts to be achieved.Different interaction patterns may also be associated with different inhibitory mechanisms.

show abstract

Section: Resultsmentioning

confidence: 99%

Profiling the interaction of 1‐phenylbenzimidazoles to cyclooxygenases

Gómez-Castro

López‐Martínez

Hernández-Pineda

et al. 2019

J of Molecular Recognition

View full text Add to dashboard Cite

show abstract

“…The pest control potency of imidazopyridine was assessed using Trichomonas Vaginalis. GT3 was a highly pathogenic strain isolated in the city of Guanajuato, Mexico in 2012 [94]. Margarita Lopez-Martinez et al showed that most of the synthezisedcompounds got antiparasitic activity after 24 h of treatment.…”

Section: H Imidazo[12-a]pyridine As a Pest Controlmentioning

confidence: 99%

Benzimidazoles and Imidazo[1,2-a]pyridines : Biological Activities, Method of Synthesis and Perspectives on Combination of Deuce Pharmacophore

Coulibaly

Evrard

Kumar

et al. 2023

Preprint

View full text Add to dashboard Cite

The N heterocyclic scaffold has generated a lot of interest among medicinal chemists. Of those potential heterocyclic drugs, benzimidazole and imidazopyridine scaffolds are considerably prevalent. They have gained tremendous importance over the past few decades. Both are an important class of molecules due to their wide spectrum of biological activities and clinical applications. Both are used in fashion design and the development of novel synthetic analogs for various therapeutic disorders. A wide variety of their derivatives have been developed as potential anti-cancer, anti-microbial, anti-viral, and anti-inflammatory besides other chemotherapeutic agents. Benzimidazole core was found in the natural system displaying a wide range of pharmaceutical properties and it gained significant attention in medicinal chemistry reported in several full articles and communications. While imidazopyridines exhibit a vast distribution in many pharmacologically important compounds shown by its frequent occurrence in a large number of marketed drug formulations and drug candidates as well as in other fields such as material and organometallic chemistry. These scaffolds are characterized as structurally potential ligands which can bind to different receptor sites for the discovery of various immerging drugs. They act as key pharmacophore motifs for the identification and optimization of lead structures to increase the medicinal chemistry toolbox. The present review outlines the synthesis and the medicinal significance of benzimidazoles and imidazopyridines for their development as lead molecules with improved therapeutic efficiencies. Here, we cover the various design used to obtain both heterocycles to establish a relationship between their combination to features the biological activities.

show abstract

“…The functionalized heterocycles demonstrate a significant biological activities in medicinal chemistry . Recently, the fused heterocyclic system functionalized imidazo[1,2‐a]pyridine has been recognized as an important pharmacophore, some of them were investigated as lipophilic parameter (log P) on the anti‐parasitic activity, docking simulations and anti‐inflammatory activity evaluation, of 2‐(N‐alkyl)amino‐3‐nitroimidazo[1,2‐a]pyridines, antiproliferative activity against melanoma cells, protein kinase inhibitors, antimicrobial activity and synergistic effects of novel organoselenium based imidazo[1,2‐a]pyridine compounds . The potential antipsychotic activity of fluorinated imidazo[1,2‐a]pyridine derivatives were also recognized as colon cancer cell lines HT‐29, and Caco‐2, antimicrobial screening, urease inhibition of 5‐substituted‐8‐methyl‐2H‐pyrido[1,2‐a]pyrimidine‐2, 4(3H)‐diones, and anticonvulsant studies of 6‐bromoimidazo[1,2‐a]pyridine‐2‐carbohydrazide derivatives …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Imidazo[1,2‐a]pyridines: C‐H Functionalization in the Direction of C‐S Bond Formation

Ravi

Adimurthy

2017

The Chemical Record

View full text Add to dashboard Cite

Imidazo[1,2-a]pyridines play an important role in medicinal chemistry. In spite of very drastic developments on syntheses and functionalization in this area, the use of inexpensive catalysts and mild reaction conditions constitutes an important role in pharmaceutical applications. This account describes our recent efforts on the development of new methods for the synthesis of imidazo[1,2-a]pyridines using readily available starting substrates and catalysts under very mild reaction conditions. In the direction of enhancement of biological activity, we also described the synthesis of functionalized imidazo [1,2-a]pyridine derivatives.

show abstract

Effect of the lipophilic parameter (log P) on the anti-parasitic activity of imidazo[1,2-a]pyridine derivatives

Cited by 15 publications

References 12 publications

Profiling the interaction of 1‐phenylbenzimidazoles to cyclooxygenases

Profiling the interaction of 1‐phenylbenzimidazoles to cyclooxygenases

Benzimidazoles and Imidazo[1,2-a]pyridines : Biological Activities, Method of Synthesis and Perspectives on Combination of Deuce Pharmacophore

Synthesis of Imidazo[1,2‐a]pyridines: C‐H Functionalization in the Direction of C‐S Bond Formation

Contact Info

Product

Resources

About