title: Efficient electrochemical N-alkylation of N-boc-protected 4-aminopyridines: towards new biologically active compounds.
abstract: The use of electrogenerated acetonitrile anion allows the alkylation of N-Boc-4-aminopyridine in very high yields, under mild conditions and without by-products. The high reactivity of this base is due to its large tetraethylammonium counterion, which leaves the acetonitrile anion "naked." The deprotection of the obtained compounds led to high yields in N-alkylated 4-aminopyridines. Nonsymmetrically dialkylated 4-aminopyridines were obtained by subsequent reaction of monoalkylated ones with t-BuOK and alkyl halides, while symmetrically dialkylated 4-aminopyridines were obtained by direct reaction of 4-aminopyridine with an excess of t-BuOK and alkyl halides. Some mono- and dialkyl-4-aminopyridines were selected to evaluate antifungal and antiprotozoal activity; the dialkylated 4-aminopyridines 3ac, 3ae and 3ff showed antifungal towards Cryptococcus neoformans; whereas 3cc, 3ee and 3ff showed antiprotozoal activity towards Leishmania infantum and Plasmodium falciparum.
authors: Department of Basic and Applied Sciences for Engineering, Sapienza University of Rome, Via Castro Laurenziano 7, 00161 Rome, Italy.
authors: Marta
authors: 0000-0002-3673-6509
authors: M
authors: Feroci
authors: Department of Basic and Applied Sciences for Engineering, Sapienza University of Rome, Via Castro Laurenziano 7, 00161 Rome, Italy.
authors: Isabella
authors: I
authors: Chiarotto
authors: Department of Basic and Applied Sciences for Engineering, Sapienza University of Rome, Via Castro Laurenziano 7, 00161 Rome, Italy.
authors: Gianpiero
authors: 0000-0003-4720-4054
authors: G
authors: Forte
authors: Department of Public Health and Infectious Diseases, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
authors: Giovanna
authors: G
authors: Simonetti
authors: Department of Public Health and Infectious Diseases, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
authors: Felicia Diodata
authors: 0000-0002-0998-9818
authors: FD
authors: D'Auria
authors: Laboratory for Microbiology, Parasitology and Hygiene (LMPH), Faculty of Pharmaceutical, Biomedical and Veterinary Sciences, Antwerp University, 2610 Antwerp, Belgium.
authors: Louis
authors: L
authors: Maes
authors: "Istituto Pasteur-Fondazione Cenci Bolognetti", Department of "Chimica e Tecnologie del Farmaco", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
authors: Daniela
authors: D
authors: De Vita
authors: "Istituto Pasteur-Fondazione Cenci Bolognetti", Department of "Chimica e Tecnologie del Farmaco", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
authors: Luigi
authors: L
authors: Scipione
authors: "Istituto Pasteur-Fondazione Cenci Bolognetti", Department of "Chimica e Tecnologie del Farmaco", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
authors: Laura
authors: L
authors: Friggeri
authors: "Istituto Pasteur-Fondazione Cenci Bolognetti", Department of "Chimica e Tecnologie del Farmaco", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
authors: Roberto
authors: R
authors: Di Santo
authors: "Istituto Pasteur-Fondazione Cenci Bolognetti", Department of "Chimica e Tecnologie del Farmaco", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
authors: Silvano
authors: S
authors: Tortorella