Synthesis and Antiplasmodial Activity of 4-Alkylidene(arylidene)hydrazono-1,3-oxazinan-2-ones and 3-Hydroxy-N′-alkylidene(arylidene)propanehydrazonamides
Mehdi Khankischpur A , Rolf D. Walter B and Thomas Kurz C DA Institute of Pharmacy, University of Hamburg, Bundesstr. 45, 20146 Hamburg, Germany.
B Bernhard Nocht Institute for Tropical Medicine, Bernhard-Nocht-Str. 74, 20359 Hamburg, Germany.
C Institute of Pharmaceutical and Medicinal Chemistry, Heinrich-Heine Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany.
D Corresponding author. Email: Thomas.Kurz@uni-duesseldorf.de
Australian Journal of Chemistry 63(10) 1430-1436 https://doi.org/10.1071/CH10052
Submitted: 28 January 2010 Accepted: 21 April 2010 Published: 1 October 2010
Abstract
Previously unreported 6-substituted 4-alkylidene(arylidene)hydrazono-1,3-oxazinan-2-ones and a series of open-chained 3-hydroxy-N′-alkylidene(arylidene)propanehydrazonamides were synthesized and evaluated for their in vitro antiplasmodial activity. The most active 3-hydroxy-N′-alkylidene(arylidene)propanehydrazonamide exhibits potent in vitro antiplasmodial activity against the chloroquine-sensitive strain 3D7 of Plasmodium falciparum and demonstrates an IC50 value of 0.2 µM.
Acknowledgements
The authors thank Miss Isabelle Nevoigt for her valuable help in the preparation of the X-ray crystal structure. Moreover, the authors thank Mrs. Baerbel Bergmann for performing the biological testing.
[1]
(a) J. A. Furch,
D. G. Kuhn,
D. A. Hunt,
M. Asselin,
S. P. Baffic,
R. E. Diehl,
Y. L. Palmer,
S. H. Trotto,
ACS Symp. Ser. 1998, 686, 178.
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