A Series of Bicyclic Insect Juvenile Hormone Analogs of Czech Origin: Twenty Years of Development

Wimmer, Zdeněk; Rejzek, Martin; Zarevúcká, Marie; Kuldová, Jelena; Hrdý, Ivan; Němec, Václav; Romaňuk, M.

doi:10.1023/b:joec.0000006399.07779.16

Cited by 45 publications

(36 citation statements)

References 25 publications

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“…These substrates were chosen because of their close structural relationship with the insect juvenile hormone bioanalogs of the 2-(4-hydroxybenzyl)cyclo hexanone series, showing promising biological activity on several non-related insect species [13,14].…”

Section: Introductionmentioning

confidence: 99%

Lipase Activity Enhancement by SC-CO₂ Treatment

2008

Zeitschrift Für Naturforschung B

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The activity of lipases from porcine pancreas, Candida antartica recombinant from Aspergillus oryzae, Candida cylindracea (immobilized), Penicilium roqueforti, Aspergillus niger, Rhizopus arrhizus, Mucor miehei (two types of immobilization), and Pseudomonas cepacia (two types of immobilization) was studied after using them as biocatalysts of blackcurrant oil hydrolysis under SC-CO 2 conditions. The reaction was performed at 40 • C and 15 MPa in a continuous-flow reactor. Increased relative activity of all used lipases after the hydrolytic reaction was observed. The most remarkable increase in the activity was noted for the lipase from Rhizopus arrhizus which was increased by more than 50 times. The highest activity was shown by Lipozyme R , lipase from Mucor miehei immobilized on macroporous resin. Both treated and untreated Lipozyme R were used as biocatalysts in hydrolytic resolution of the racemic cis-or trans-isomers of 2-(4-methoxybenzyl)cyclohexyl acetates. Satisfactory reaction yields (40 %) and excellent enantiomeric purity of the products (E = 472) were obtained when hydrolysis of the trans-isomer of 2-(4-methoxybenzyl)cyclohexyl acetate was catalyzed by Lipozyme R treated with SC-CO 2 .

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Section: Introductionmentioning

confidence: 99%

Lipase Activity Enhancement by SC-CO₂ Treatment

2008

Zeitschrift Für Naturforschung B

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“…More than 20 years ago, we had used cadmium carbonate [6] for a successful synthesis of 2-[4-(3-ethoxy-3-methyl-1-butoxy)benzyl]cyclohexyl-β-D-glucopyranosides, derived from the separated racemic cis and trans isomers of 2-[4-(3-ethoxy-3-methyl-1-butoxy)benzyl]cyclohexanol, insect juvenile hormone bioanalogs [7]. At that time, only 100 MHz NMR spectra of 2-[4-(3-ethoxy-3-methyl-1-butoxy)benzyl]cyclohexyl-β-D-glucopyranoside products were measured, which ultimately were not published [6].…”

Section: Introductionmentioning

confidence: 99%

Koenigs-Knorr Synthesis of Cycloalkyl Glycosides

2004

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Cadmium carbonate was found to be a useful promoter in the Koenigs-Knorr synthesis of 2-(4-methoxybenzyl)cyclohexyl-β-D-glycopyranosides. Using this promoter model glucoside and galactoside derivatives of cyclic (i.e., secondary) alcohols were synthesized in 50-60 % overall yields. Diastereoisomeric mixtures of products were obtained in these syntheses, which started from racemic isomers of 2-(4-methoxybenzyl)cyclohexanol. The prepared compounds have been purified and characterized by their 1 H-and 13 C-NMR spectra, as well as by their IR and MS spectra, in order to use them as reference compounds in planned subsequent research.

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“…1) was developed as a part of a series of insect juvenile hormone analogs (juvenoids), structurally derived from 2-(4-hydroxybenzyl)-1-cycloalkanones (Wimmer et al, 1985;. After 20 years of investigation of these compounds, a review has been recently published covering the key results (Wimmer et al, 1997). The principal achievements are the augmentation of what is known about the structure-activity relationships of the compounds and their effects on non-related insect species, the selection of compounds displaying potentially practical applicability, and the establishment of a basis for future investigation of juvenile hormone analog/binding protein complexes.…”

Section: Introductionmentioning

confidence: 99%

Degradation of a radiolabeled juvenile hormone analog using two insect species

Wimmer

Tykva

Bennettová

et al. 1997

Invertebrate Neuroscience

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A synthetic insect juvenile hormone analog (a juvenoid), ethyl N-[2-[4-[[2,2-(ethylenedioxy)cyclohexyl]methyl]phenox]ethyl]carbam ate, which has displayed high biological activity against different insect species and high stability under field conditions, was selected as a biologically active model compound for a study of a juvenile hormone analog degradation. The biologically active compound itself and its three diversely radiolabeled derivatives were applied to the flesh fly (Sarcophaga bullata) or the tsetse fly (Glossina palpalis), respectively. Monitoring of a fate of the applied juvenile hormone analog was carried out using a detection method of the radioactivity microdistribution within the whole insect body in combination with a radio high performance liquid chromatography (radio-HPLC), both of whole-body extracts made in different, but in advance scheduled, time intervals, and of extracts of insect excreta accumulated over an eight-day experiment.

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A Series of Bicyclic Insect Juvenile Hormone Analogs of Czech Origin: Twenty Years of Development

Cited by 45 publications

References 25 publications

Lipase Activity Enhancement by SC-CO₂ Treatment

Lipase Activity Enhancement by SC-CO₂ Treatment

Koenigs-Knorr Synthesis of Cycloalkyl Glycosides

Degradation of a radiolabeled juvenile hormone analog using two insect species

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A Series of Bicyclic Insect Juvenile Hormone Analogs of Czech Origin: Twenty Years of Development

Cited by 45 publications

References 25 publications

Lipase Activity Enhancement by SC-CO2 Treatment

Lipase Activity Enhancement by SC-CO2 Treatment

Koenigs-Knorr Synthesis of Cycloalkyl Glycosides

Degradation of a radiolabeled juvenile hormone analog using two insect species

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Product

Resources

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Lipase Activity Enhancement by SC-CO₂ Treatment

Lipase Activity Enhancement by SC-CO₂ Treatment