4-Aminoquinolines have been recently indicated as an important class of chemotherapeutic agents for artemisinin-based antimalarial combination therapy. Therefore, a rapid, cheap, possibly clean and scalable access to 4-aminoquinolines endowed with multiple diversity is largely requested. Classically, they have been prepared via SNAr requiring hazardous or costly reagents and conditions, and complex purification procedures. In this paper, microwave flash-heating chemistry is shown to allow the efficient conversion of the available 4,7-dichloroquinoline into a library of aminoquinolines in high yield and purity, without further purification steps and requiring very short reaction times. Some of the compounds among this library were active against chloroquine-sensitive and chloroquine-resistant parasite strains.

Melato, S., Coghi, P., Basilico, N., Prosperi, D., & Monti, D. (2007). Novel 4-aminoquinolines by microwave-assisted SNAr reaction: a practical route to antimalarial agents. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007(36), 6118-6123 [10.1002/ejoc.200700612].

Novel 4-aminoquinolines by microwave-assisted SNAr reaction: a practical route to antimalarial agents

PROSPERI, DAVIDE;
2007

Abstract

4-Aminoquinolines have been recently indicated as an important class of chemotherapeutic agents for artemisinin-based antimalarial combination therapy. Therefore, a rapid, cheap, possibly clean and scalable access to 4-aminoquinolines endowed with multiple diversity is largely requested. Classically, they have been prepared via SNAr requiring hazardous or costly reagents and conditions, and complex purification procedures. In this paper, microwave flash-heating chemistry is shown to allow the efficient conversion of the available 4,7-dichloroquinoline into a library of aminoquinolines in high yield and purity, without further purification steps and requiring very short reaction times. Some of the compounds among this library were active against chloroquine-sensitive and chloroquine-resistant parasite strains.
Articolo in rivista - Articolo scientifico
Heterocycles; Aromatic substitution; Antimalarial agents; Microwave irradiation; Aminoquinolines
English
Melato, S., Coghi, P., Basilico, N., Prosperi, D., & Monti, D. (2007). Novel 4-aminoquinolines by microwave-assisted SNAr reaction: a practical route to antimalarial agents. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007(36), 6118-6123 [10.1002/ejoc.200700612].
Melato, S; Coghi, P; Basilico, N; Prosperi, D; Monti, D
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10281/7905
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