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.
Comment
HCQ is synthesized by reacting a diamine with 4,7-dichloroquinoline in an S N Ar 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).
References
- Surrey A R, Hammer H F.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. 1950721814–1815. [Google Scholar]