Synthesis of 5-substituted analogues of huperzine A.
Three 5-isosteres of huperzine A (2-4) were first synthesized. The key intermediate 10 was prepared by the reaction of acid 13 with LTA. The compounds 2 and 3 had 50% inhibition by 35 and 47 microM, respectively, which still retained antiacetylcholinesterase activity.
Zhou
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GC
State Key Laboratory for Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, People's Republic of China.
Zhu
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DY
D000110:Acetylcholinesterase / Q000378:metabolism; D000470:Alkaloids; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000470:Alkaloids; D002800:Cholinesterase Inhibitors; D012717:Sesquiterpenes; C050426:huperzine A; D000110:Acetylcholinesterase