0000000000390404

AUTHOR

Francesco Risitano

showing 2 related works from this author

Synthesis of C3/C1-Substituted Tetrahydroisoquinolines

2015

A broad biological screening of the natural alkaloid N-methylisosalsoline (2) extracted from Hammada scoparia leaves against a panel of human and parasitic proteases revealed an interesting activity profile of 2 towards human 20S proteasome. This outcome suggests that the 1,2,3,4-tetrahydroisoquinoline skeleton may be exploited as a template for the development of novel anticancer agents. In this article, we report the synthesis and chemical characterization of a new series of isosalsoline-type alkaloids (10-11) with variations at N2 and C3 positions with respect to the natural Compound 2, obtained by a synthetic strategy that involves the Bischler-Napieralski cyclization. The substrate for…

Proteases<i>N</i>-methylisosalsolineStereochemistryPharmaceutical SciencenitroalkeneNitroalkene20s proteasomeArticleAnalytical Chemistrylcsh:QD241-441chemistry.chemical_compoundlcsh:Organic chemistryTetrahydroisoquinolinesN-methylisosalsolineDrug DiscoveryAnimalsHumansParasitesPhysical and Theoretical ChemistryBischler-Napieralski condensationCell ProliferationBischler-Napieralski condensation; N-methylisosalsoline; nitroalkene; proteasome; tetrahydroisoquinolineChemistryTetrahydroisoquinolineAlkaloidOrganic ChemistrySubstrate (chemistry)Hammada scopariaproteasomeChemistry (miscellaneous)Molecular MedicineCattleAmine gas treatingtetrahydroisoquinolinePeptide Hydrolases
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Direct synthesis of C3-mono-functionalized oxindoles from N-unprotected 2-oxindole and their antileishmanial activity.

2014

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.

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 infantumBioorganicmedicinal chemistry
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