3-Benzylidenemyosmine analogues with substituents at the
ortho-,
meta-, and
para-positions of the phenyl ring and 3-cinnamylidenemyosmine analogues with substituents at a
para-position of the phenyl ring were synthesized. The affinity of the synthesized compounds for nicotinic acetylcholine receptors (nAChRs) in the nerve cord of the American cockroach (
Periplaneta americana L.) was determined by radioligand binding assay using [
3H]epibatidine. Of the compounds tested, 3-(2,4-dihydroxybenzylidene)myosmine
3 and 3-(4-hydroxybenzylidene)myosmine
4 displayed the highest potency, with IC
50 values of 0.120 and 0.310 μM, respectively. 3-(4-Dimethylaminobenzylidene)myosmine
15 with a
para-dimethylamino group on the benzylidene moiety displayed moderate affinity (IC
50=5.49 μM). On the other hand, cinnamylidene analogues, 3-(4-dimethylaminocinnamylidene)myosmine
16 and 3-cinnamylidenemyosmine
17, displayed moderate affinity, with IC
50 values of 2.07 and 3.52 μM, respectively.
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