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Synfacts 2020; 16(06): 0716
DOI: 10.1055/s-0040-1706950
Chemistry in Medicine and Biology
© Georg Thieme Verlag Stuttgart · New York

Hydroxychloroquine – An Antimalarial to Fight COVID-19?

Contributor(s):
Dirk Trauner
,
Alexander J. E. Novak
Surrey AR, Hammer HF. Sterling-Winthrop Research Institute, Rensselaer, USA
The Preparation of 7-Chloro-4-(4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino)-quinoline and Related Compounds.

J. Am. Chem. Soc. 1950;
72: 1814-1815
Further Information

Publication History

Publication Date:
15 May 2020 (online)

 
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Key words

SARS-CoV-2 - COVID-19 - antimalarial

Significance

Hydroxychloroquine (HCQ) and chloroquine (CQ) have long been used as treatments for malaria and autoimmune diseases. Surrey and Hammer detailed the synthesis of HCQ, a potent antimalarial in 1950. In an effort to identify available drugs to fight SARS-CoV-2 it has been reported that CQ and HCQ in combination with azithromycin might have the potential to combat COVID-19.


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Comment

HCQ is synthesized by reacting a diamine with 4,7-dichloroquinoline in an SNAr reaction. The diamine is synthesized by condensing 5-chloro-2-pentanone with N-ethylethanolamine, followed by reductive amination with ammonia. HCQ showed good antimalarial activity and recently has been found to inhibit SARS-CoV-2 infection in vitro (Cell Discovery 2020, 6, 16).


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