title: Direct synthesis of C3-mono-functionalized oxindoles from N-unprotected 2-oxindole and their antileishmanial activity.
abstract: 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.
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Messina, V.le F.Stagno d'Alcontres 31, Messina 98166, Italy; CNR-ISMN Istituto per lo Studio dei Materiali Nanostrutturati, UOS Palermo, c/o Dip. Scienze Chimiche, Università di Messina, V.le F.Stagno d'Alcontres 31, Messina 98166, Italy.
authors.forename: Angela
authors.initials: A
authors.lastname: Scala
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Messina, V.le F.Stagno d'Alcontres 31, Messina 98166, Italy.
authors.forename: Massimiliano
authors.initials: M
authors.lastname: Cordaro
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Messina, V.le F.Stagno d'Alcontres 31, Messina 98166, Italy.
authors.forename: Giovanni
authors.initials: G
authors.lastname: Grassi
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Messina, V.le F.Stagno d'Alcontres 31, Messina 98166, Italy.
authors.forename: Anna
authors.initials: A
authors.lastname: Piperno
authors.affiliation: Dipartimento di Patologia Umana, Università di Messina, Viale Consolare Valeria 1, Messina 98125, Italy.
authors.forename: Giuseppina
authors.initials: G
authors.lastname: Barberi
authors.affiliation: Dipartimento di Patologia Umana, Università di Messina, Viale Consolare Valeria 1, Messina 98125, Italy.
authors.forename: Antonio
authors.initials: A
authors.lastname: Cascio
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Messina, V.le F.Stagno d'Alcontres 31, Messina 98166, Italy. Electronic address: frisitano@unime.it.
authors.forename: Francesco
authors.initials: F
authors.lastname: Risitano
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line / Q000187:drug effects; D002599:Chalcone; D060326:Chemistry Techniques, Synthetic; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical / Q000379:methods; D007211:Indoles / Q000737:chemistry*; D018314:Leishmania infantum / Q000187:drug effects*; D051379:Mice; D000078183:Oxindoles; D013329:Structure-Activity Relationship; D018675:Toxicity Tests
chemical_list: D000981:Antiprotozoal Agents; D007211:Indoles; D000078183:Oxindoles; C456900:indolin-2-one; C022960:2-oxindole; D002599:Chalcone
keywords: Cyclization; Diastereoselectivity; Leishmania; Leishmanicidal activity; Michael addition; Oxindoles