title: A new vinyl selenone-based domino approach to spirocyclopropyl oxindoles endowed with anti-HIV RT activity.
abstract: Herein, we disclose a general and flexible access to spirocyclopropyl oxindoles by a domino Michael/intramolecular nucleophilic substitution pathway with variously substituted vinyl selenones and enolizable oxindoles in aqueous sodium hydroxide solution. The spirocyclopropyl oxindole being a privileged scaffold, some of the synthesized compounds were selected for biological evaluation. Compound showed selective anti-HIV-1 activity thanks to its ability to inhibit the reverse transcriptase.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy. francesca.marini@unipg.it.
authors.forename: M
authors.initials: M
authors.lastname: Palomba
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy. francesca.marini@unipg.it.
authors.forename: L
authors.initials: L
authors.lastname: Rossi
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy. francesca.marini@unipg.it.
authors.forename: L
authors.initials: L
authors.lastname: Sancineto
authors.affiliation: Dipartimento di Scienze della Vita e dell'Ambiente, Cittadella Universitaria di Monserrato SS554 - 09042, Monserrato (Cagliari), Italy.
authors.forename: E
authors.initials: E
authors.lastname: Tramontano
authors.affiliation: Dipartimento di Scienze della Vita e dell'Ambiente, Cittadella Universitaria di Monserrato SS554 - 09042, Monserrato (Cagliari), Italy.
authors.forename: A
authors.initials: A
authors.lastname: Corona
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy. francesca.marini@unipg.it.
authors.forename: L
authors.initials: L
authors.lastname: Bagnoli
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy. francesca.marini@unipg.it.
authors.forename: C
authors.initials: C
authors.lastname: Santi
authors.affiliation: KU Leuven, Department of Microbiology and Immunology, Laboratory of Virology and Chemotherapy, Rega Institute for Medical Research, B-3000 Leuven, Belgium.
authors.forename: C
authors.initials: C
authors.lastname: Pannecouque
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy. francesca.marini@unipg.it.
authors.forename: O
authors.initials: O
authors.lastname: Tabarrini
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy. francesca.marini@unipg.it.
authors.forename: F
authors.initials: F
authors.lastname: Marini
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006678:HIV / Q000187:drug effects* / Q000201:enzymology*; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D016566:Organoselenium Compounds / Q000737:chemistry / Q000494:pharmacology; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014753:Vinyl Compounds / Q000737:chemistry / Q000494:pharmacology; D014779:Virus Replication / Q000187:drug effects
chemical_list: D019380:Anti-HIV Agents; D003521:Cyclopropanes; D007211:Indoles; D016566:Organoselenium Compounds; D018894:Reverse Transcriptase Inhibitors; D013141:Spiro Compounds; D014753:Vinyl Compounds; D054303:HIV Reverse Transcriptase