Synthesis and Biological Evaluation of 2H-Indazole Derivatives: Towards Antimicrobial and Anti-Inflammatory Dual Agents

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Jaime Pérez-VillanuevaDante B Estrada-Castro

Abstract

Indazole is considered a very important scaffold in medicinal chemistry. It is commonly found in compounds with diverse biological activities, e.g., antimicrobial and anti-inflammatory agents. Considering that infectious diseases are associated to an inflammatory response, we designed a set of 2H-indazole derivatives by hybridization of cyclic systems commonly found in antimicrobial and anti-inflammatory compounds. The derivatives were synthesized and tested against selected intestinal and vaginal pathogens, including the protozoa Giardia intestinalis, Entamoeba histolytica, and Trichomonas vaginalis; the bacteria Escherichia coli and Salmonella enterica serovar Typhi; and the yeasts Candida albicans and Candida glabrata. Biological evaluations revealed that synthesized compounds have antiprotozoal activity and, in most cases, are more potent than the reference drug metronidazole, e.g., compound 18 is 12.8 times more active than metronidazole against G. intestinalis. Furthermore, two 2,3-diphenyl-2H-indazole derivatives (18 and 23) showed in vitro growth inhibition against Candida albicans and Candida glabrata. In addition to their antimicrobial activity, the anti-inflammatory potential for selected compounds was evaluated in s...Continue Reading

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Citations

Jun 5, 2018·ChemMedChem·Jinyun DongShaoshun Li
Nov 26, 2019·Current Pharmaceutical Design·Jéssika de Oliveira VianaMarcus Tullius Scotti
Nov 7, 2019·Organic & Biomolecular Chemistry·Kim Christopher C AgandaAnna Lee
Apr 30, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Abida KhanMd Afroz Bakht
Dec 29, 2020·European Journal of Medicinal Chemistry·Jaime Pérez-VillanuevaOlivia Soria-Arteche
Mar 7, 2021·Pharmaceuticals·Karen Rodríguez-VillarJaime Pérez-Villanueva
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Karen Rodríguez-VillarJaime Pérez-Villanueva
Aug 29, 2021·Pharmaceuticals·Jaime Pérez-VillanuevaOlivia Soria-Arteche

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Methods Mentioned

BETA
nuclear magnetic resonance
column chromatography

Software Mentioned

AutoDock Vina
Autodock Tools
YASARA
Maestro
ChemBioDraw Ultra
UCSF Chimera package
OriginPro

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