3-Benzylideneanabaseine analogues with electron-donating
ortho- and/or
para-substituents on the benzene ring were synthesized. The affinity of the analogues for nicotinic acetylcholine receptors in the nerve cord of the American cockroach (
Periplaneta americana L.) was determined by the radioligand binding assay using [
3H]epibatidine. Among the compounds tested, 3-(4-hydroxybenzylidene)anabaseine (
6) displayed the highest potency, with IC
50 values of 3.6 nM. In contrast, 3-(4-methoxybenzylidene)anabaseine (
5) showed the lowest potency (IC
50=188.3 nM). Compound
6 was found to have 52-fold higher affinity than
5. 3-(2,4-Dimethoxybenzylidene)anabaseine (
1) and 3-(2-hydroxy-4-methoxybenzylidene)anabaseine (
2) showed higher potency than
5, with IC
50 values of 41.6 and 63.5 nM, respectively. Compound
6 might prove to be a good lead compound for the development of novel insecticides.
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