B. Venugopalan et al., ANTIMALARIAL ACTIVITY OF NOVEL RING-CONTRACTED ARTEMISININ DERIVATIVES, Journal of medicinal chemistry, 38(11), 1995, pp. 1922-1927
Bromoacetal 2 undergoes a novel ring-contracted reaction to give the a
ldehyde 3 in the presence of DBU or triethylamine. The aldehyde 3 is r
educed to the alcohol 4 and oxidized to the carboxylic acid 5. The alc
ohol 4 reacts with dihydroartemisinin to give the two diastereoisomers
38 and 39. All the compounds were tested for antimalarial activity in
mice infected with chloroquine sensitive Plasmodium berghei. If the a
ctivity of a compound was comparable to that of the standard compound,
such as arteether, it was tested against chloroquine resistant NS str
ain infection in mice. Initially the compounds were administered subcu
taneously, and if found to be active, they were tested by oral route.
The antimalarial activity of compounds 19, 38, and 39 was found to be
comparable to that of arteether when tested in K-173-infected mice. Th
ey were also active against chloroquine resistant NS strain infection
in mice.