Synthesis of new arylaminoquinoxalines and their antimalarial activity in mice

2‐Arylaminoquinoxalines were prepared by the condensation of 2‐chloroquinoxaline with the appropriate Mannich bases in the presence of HCl. To synthesize the Mannich bases, 4‐acetamidophenol was reacted with formaldehyde and dialkylamine to yield 3‐[(dialkylamino) methyl]‐4‐hydroxyacetanilide, follo...

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Bibliographic Details
Published in:Journal of pharmacy and pharmacology 2001-10, Vol.53 (10), p.1409-1413
Main Authors: Rangisetty, J. B., Gupta, C. N. V. H. B., Prasad, A. L., Srinivas, P., Sridhar, N., Parimoo, P., Veeranjaneyulu, A.
Format: Article
Language:English
Subjects:
Animals
Antimalarials - chemical synthesis
Antimalarials - pharmacology
Chloroquine - pharmacology
Indicators and Reagents
Malaria - blood
Malaria - drug therapy
Malaria - parasitology
Mannich Bases
Mice
Plasmodium yoelii
Plasmodium yoelii - drug effects
Quinoxalines - chemical synthesis
Quinoxalines - pharmacology
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Summary:2‐Arylaminoquinoxalines were prepared by the condensation of 2‐chloroquinoxaline with the appropriate Mannich bases in the presence of HCl. To synthesize the Mannich bases, 4‐acetamidophenol was reacted with formaldehyde and dialkylamine to yield 3‐[(dialkylamino) methyl]‐4‐hydroxyacetanilide, followed by hydrolysis. Antimalarial activities of the new arylaminoquinoxalines were evaluated against the rodent malaria parasite Plasmodium yoelii at a dose of 75 mg kg−1. Three compounds synthesized (2‐[3‐[(diethylamino) methyl]‐4‐hydroxy‐anilino]‐quinoxaline dihydrochloride (2b), 2‐[3‐[(pyrrolidinyl) methyl]‐4‐hydroxyanilino]‐quinoxaline dihydrochloride (2f), and 2‐[3‐[(piperidinyl) methyl]‐4‐hydroxyanilino]‐quinoxaline dihydrochloride (2g)) showed moderate antimalarial activity.
ISSN:0022-3573
2042-7158
DOI:10.1211/0022357011777765