Regioselective Mannich reaction of phenolic compounds and its application to the synthesis of new chitosan derivatives
A regioselective aminomethylation of 2,4-dihydroxybenzoyl compounds at the C(3) position was accomplished through a Mannich reaction of phenolic substrates with formaldehyde and secondary amines in methanol, whereas the reaction with primary amines included a subsequent cyclization step to yield the 1,3-benzoxazine derivatives. This sequence was successfully applied to the one-pot introduction of N-benzyl side chains to chitosan, a natural polyaminosaccharide, to afford a new chitosan derivative with improved solubility in an organic solvent.
Synthesis and biological evaluation of phenolic Mannich bases of benzaldehyde and (thio)semicarbazone derivatives against the cysteine protease falcipain-2 and a chloroquine resistant strain of Plasmodium falciparum
A targeted series of phenolic Mannich bases of benzaldehyde and (thio)semicarbazone derivatives were synthesized and evaluated in vitro against the malarial cysteine protease falcipain-2 and a chloroquine resistant strain (W2) of Plasmodium falciparum. A
Chipeleme, Alex,Gut, Jiri,Rosenthal, Philip J.,Chibale, Kelly
p. 273 - 282
(2008/02/03)
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