- Synthesis and structure-activity relationships of juvenoids derived from 2-(4-hydroxybenzyl)cycloalkan-1-ones
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Juvenoids 16-30, 32, 36, 38-41, 44-46, and 49-56 containing carbamate, carbonate, and urea moieties in the molecule were synthesized and subjected to a biological screening. Carbamate juvenoids 1-4 were used as reference compounds for a detailed structure-activity study of their analogues. A clear relationship between the nature of the side chain functional group and the biological activity was found. Surprisingly, not only the juvenoids 1,4 but also 38-41, the compounds with a reversed carbamate N,O-substitution pattern, showed very promising biological activity. In contrast, the carbonate and urea derivatives displayed a remarkably low activity. The relationship between the size and substitution at atoms C(2) and C(3) of the saturated ring and the biological activity is very complex and is still not completely understood.
- Rejzek,Wimmer,Saman,Ricankova,Nemec
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p. 1241 - 1255
(2007/10/02)
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- Carbamate series of juvenoids: Variation of the O-alkyl substituent
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By changing the O-alkyl substituents of the carbamate moiety of alkyl N-{2-{4-[(2-oxocyclohexyl)methyl]phenoxy}ethyl}carbamates and subsequent transformation of the oxo group in the cyclohexyl substituent, the juvenoids 1-20 were synthesized (Scheme). The methyl (1-4), propyl (9-12), isopropyl (13-16), and prop-2-ynylcarbamates (17-20) were subjected to biological screening on several non-related insect species (Tenebrio molitor, Galleria mellonella, Dysdercus cingulatus, and Pyrrhocoris apterus). Some of the juvenoids showed high biological activity and excellent selectivity with respect to target insect species (Table 2).
- Wimmer,Saman,Nemec,Francke
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p. 561 - 568
(2007/10/02)
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- Oxime Ethers as Potential Juvenoids
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The oxime ethers 7a-14a and 7b-10b were synthesized in order to study their potential insecticidal properties.The respective syn- (7a-10a) and anti-isomers (7b-10b) of the oxime ethers were separated.Only syn-isomer formation was observed during the synth
- Wimmer, Zdenek,Saman, David,Smolikova, Jorga,Romanuk, Miroslav
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p. 1091 - 1094
(2007/10/02)
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