Synthesis, antiprotozoal activity, and chemoinformatic analysis of 2-(methylthio)-1H-benzimidazole-5-carboxamide derivatives: Identification of new selective giardicidal and trichomonicidal compounds
| Autor: | Rafael Castillo, Alicia Hernández-Campos, Rodrigo Aguayo-Ortiz, Paulina Flores-Carrillo, Pedro Josué Trejo-Soto, José Miguel Velázquez-López, Lilián Yépez-Mulia |
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| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Benzimidazole medicine.drug_class Antiparasitic Stereochemistry Antiprotozoal Agents Carboxamide medicine.disease_cause 01 natural sciences Albendazole 03 medical and health sciences chemistry.chemical_compound Entamoeba histolytica Structure-Activity Relationship Parasitic Sensitivity Tests Drug Discovery medicine Trichomonas vaginalis Pharmacology biology Dose-Response Relationship Drug Molecular Structure 010405 organic chemistry Chemistry Organic Chemistry Nitazoxanide General Medicine biology.organism_classification 0104 chemical sciences 030104 developmental biology Antiprotozoal Benzimidazoles Giardia lamblia medicine.drug |
| Zdroj: | European journal of medicinal chemistry. 137 |
| ISSN: | 1768-3254 |
| Popis: | A series of twelve new 2-(methylthio)-1 H -benzimidazole-5-carboxamide derivatives ( 1 − 12 ) were synthesized and their antiparasitic activity was tested in vitro against Giardia intestinalis , Trichomonas vaginalis and Entamoeba histolytica . Experimental evaluations showed IC 50 values within the nanomolar range for all tested compounds, some showing higher activity than metronidazole and albendazole. A chemoinformatic study was used to compare the structure-activity relationship of the synthesized carboxamides with those of 91 previously studied benzimidazoles, and with some Nitazoxanide– N -methylbenzimidazole hybrids recently synthetized by our group. Compounds 1 and 3 were identified as prominent selective compounds against T. vaginalis and G. intestinalis , respectively, while compound 4 was found to be of broad spectrum against the three protozoans. |
| Databáze: | OpenAIRE |
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