2006
DOI: 10.1584/jpestics.g06-11
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Affinity of 3-benzylidene- and 3-cinnamylidenemyosmine analogues for Periplaneta americana nicotinic acetylcholine receptors

Abstract: 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 [ 3 H]epibatidine. Of the compounds tested, 3-(2,4-dihydroxybenzylidene)myosmine 3 … Show more

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Cited by 6 publications
(5 citation statements)
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“…In contrast, an analogue (6) with a parahydroxyl group displayed the highest potency among the analogues synthesized, with an IC 50 value of 3.6 nM for Pa-nAChRs. The potency of 6 was 4-and 86-fold higher than those of the previously reported para-hydroxyl counterparts of CBA 7) and BM, 8) respectively. These results suggest that (i) the para-hydroxyl group that has a sufficient electron-donating effect increases its negative charge on the imine nitrogen atom by a resonance effect via the conjugated double-bond system, which eventually enhances the affinity for Pa-nAChRs, (ii) the ortho-hydroxyl group is not as effective as the para-hydroxyl group, and (iii) the para-methoxy group rather lowers the affinity of BA, although the decrease in affinity is somewhat compensated for by the introduction of an electron- donating group at the ortho-position.…”
Section: Resultscontrasting
confidence: 54%
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“…In contrast, an analogue (6) with a parahydroxyl group displayed the highest potency among the analogues synthesized, with an IC 50 value of 3.6 nM for Pa-nAChRs. The potency of 6 was 4-and 86-fold higher than those of the previously reported para-hydroxyl counterparts of CBA 7) and BM, 8) respectively. These results suggest that (i) the para-hydroxyl group that has a sufficient electron-donating effect increases its negative charge on the imine nitrogen atom by a resonance effect via the conjugated double-bond system, which eventually enhances the affinity for Pa-nAChRs, (ii) the ortho-hydroxyl group is not as effective as the para-hydroxyl group, and (iii) the para-methoxy group rather lowers the affinity of BA, although the decrease in affinity is somewhat compensated for by the introduction of an electron- donating group at the ortho-position.…”
Section: Resultscontrasting
confidence: 54%
“…On the basis of our previous findings that the introduction of a para-hydroxyl group into the benzene ring of BM increased the binding affinity for Pa-nAChRs, whereas BM analogues with a meta-hydroxyl group or a meta-methoxy group showed little affinity, 8) we synthesized BA analogues (1-6) with electrondonating ortho-and/or para-substituents on the benzene ring, and examined the affinity for Pa-nAChRs. All test compounds inhibited the specific binding of [ 3 H]epibatidine to P. americana nerve cord membranes in the nanomolar range.…”
Section: Resultsmentioning
confidence: 99%
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“…Pyrrole derivatives are regarded as privileged structural motifs found in numerous bioactive compounds and functional materials. Among them, 4‐alkylidene‐3,4‐dihydro‐2 H ‐pyrroles have an inhibitory activity on lanosterol synthase [1a] and an affinity for nicotinic acetylcholine receptors [1b] . In addition, their benzylidene analogues can serve as a molecular switch based on rhodopsin‐like E / Z photoisomerization [2] .…”
Section: Introductionmentioning
confidence: 99%
“…In addition, their benzylidene analogues can serve as a molecular switch based on rhodopsin‐like E / Z photoisomerization [2] . These compounds have been synthesized by intramolecular aza‐Wittig reactions of α ‐azidoethyl‐ α , β ‐enones using Ph 3 P, [1a,2a,b] by cyclization reactions of nitrilium ions (nitrilium cyclization) derived from homoallyl carboxamides, [2c,3a] by metathesis reactions of alkynyl Fischer carbene complexes with imines [2d] and by condensation reactions of dihydropyrroles with aldehydes [1b,4] . As the alternative methods, the cyclization of other acyclic precursors, [3] nitrilium cyclization of 1,3‐diols [5a,b] or vinylidenecyclopropanes [5c] with nitriles, and miscellaneous methods [6] have been known.…”
Section: Introductionmentioning
confidence: 99%