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Novel 4‐Aminoquinolines through Microwave‐Assisted S N Ar Reactions: a Practical Route to Antimalarial Agents
Author(s) -
Melato Sergio,
Coghi Paolo,
Basilico Nicoletta,
Prosperi Davide,
Monti Diego
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700612
Subject(s) - aminoquinolines , chemistry , combinatorial chemistry , reagent , artemisinin , flash (photography) , organic chemistry , plasmodium falciparum , malaria , art , visual arts , immunology , biology
Abstract 4‐Aminoquinolines have recently been indicated to be an important class of chemotherapeutic agents for artemisinin‐based antimalarial combination therapy. A rapid, cheap, possibly clean and scalable route to 4‐aminoquinolines endowed with multiple diversity is therefore badly needed. Classically, they have been prepared by means of S N Ar reactions, 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 yields and purities, with no need for further purification steps and requiring very short reaction times. Some of the compounds in this library were active against chloroquine‐sensitive and chloroquine‐resistant parasite strains.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)