6533b829fe1ef96bd128b023

RESEARCH PRODUCT

Direct synthesis of C3-mono-functionalized oxindoles from N-unprotected 2-oxindole and their antileishmanial activity.

Massimiliano CordaroGiuseppina BarberiFrancesco RisitanoAngela ScalaAnna PipernoGiovanni GrassiAntonio Cascio

subject

DiastereoselectivityLeishmanicidal activityIndolesStereochemistryClinical BiochemistryAntiprotozoal AgentsDrug Evaluation PreclinicalPharmaceutical Science2-oxindoleChemistry Techniques SyntheticBiochemistryCell LineMiceStructure-Activity RelationshipChalconeMichael additionparasitic diseasesDrug DiscoveryToxicity TestsAnimalsLeishmania infantumAmastigoteMolecular BiologyLeishmaniaOxindoles; Michael addition; Leishmania; Leishmanicidal activity; Diastereoselectivity; CyclizationbiologyDose-Response Relationship DrugChemistryOrganic Chemistrybiology.organism_classificationLeishmaniaCombinatorial chemistryIn vitroOxindolesCyclizationMichael reactionMolecular MedicineOxindoleLeishmania infantum

description

A novel approach for the synthesis of unprecedented C3-mono-functionalized indolin-2-ones is reported, starting from 2-oxindole and chalcones. The reactions proceed regioselectively under mild conditions, without di- and tri-alkylated side products. The new compounds have been evaluated in vitro for their antiproliferative effects against the protozoan Leishmania infantum. Interestingly, they appear able to kill L. infantum promastigotes and amastigotes, without significant cytotoxic effects.

yearjournalcountryeditionlanguage
2014-01-01Bioorganicmedicinal chemistry
10.1016/j.bmc.2013.12.039https://pubmed.ncbi.nlm.nih.gov/24433962