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  • 1
    ISSN: 1573-1561
    Keywords: Insect juvenile hormone analogs ; 2-(4-hydroxybenzyl)-1-cycloalkanones ; Tenebrio molitor ; Coleoptera ; Tenebrionidae ; Dysdercus cingulatus ; Pyrrhocoris apterus ; Heteroptera ; Pyrrhocoridae ; Acyrthosiphon pisum ; Phorodon humuli ; Homoptera ; Aphididae ; Locusta migratoria migratortorioides ; Orthoptera ; Acrididae ; Reticulitermes lucifugus ; Prorhinotermes simplex ; Isoptera ; Rhinotermitidae ; Blattella germanica ; Blattodea ; Blattidae ; Musca domestica ; Diptera ; Muscidae ; Daphnia magna Cladocera ; Daphnidae ; Trypanosoma cruzi ; Euglenozoa ; Trypanosomatidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Research results are summarized from a series of insect juvenile hormone analogs derived from 2-(4-hydroxybenzyl)-1-cycloalkanones, which have been investigated at the Institute of Organic Chemistry and Biochemistry in Prague during the past 20 years. At present, practical application of several prospective structures for insect control is under investigation. Biological activity values were determined to delineate the most important subseries of compounds and the most promising insect juvenile hormone analogs selected from the subseries. Carbamates, and in particular compound 47 proved to be highly active against aphids, cockroaches, flies, and many other insect species.
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  • 2
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 676-681 
    ISSN: 0899-0042
    Keywords: β-glucosidase from almond ; reverse hydrolysis ; transglucosylation ; enantioselectivity ; enantiomeric excess ; absolute configuration ; alkyl β-D-glucopyranoside ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Almond β-glucosidase was used to catalyze the synthesis of alkyl β-d-glucopyranosides 1b-3b starting from either d-glucose (4) or phenyl-β-d-glucopyranoside (5) and the racemic alcohols 1a-3a. The enzymic reactions were provided in different acetonitrile/water mixtures [9:1 (v/v) for the reverse hydrolysis, and 1:9 (v/v) for the transglycosylation]. Both enzymic reactions, that is, the reverse hydrolysis and the transglucosylation, are enantioselective processes. The enantiomeric purity of products 1b-2b of the enzymic reactions varied between 75 and 86% ee, the values of which were based on the analysis of the aglyconic parts (1c-2c) of the alkyl β-d-glucopyranoside molecules (1b-2b). Chirality 10:676-681, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 502-508 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of insect juvenile hormone analogs (juvenoids) was synthesized and studied. The basic skeleton of these juvenoids contains three rings and a short aliphatic subunit and bears two or three chiral centers (depending on the appropriate structure; see 6-9). The chiral center located in the 1,2-diphenoxypropane subunit has the configuration (RS), (R) (a series), or (S) (b series). The juvenoids were subjected to a biological screening, the preliminary results of which are briefly described.
    Additional Material: 1 Ill.
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  • 4
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 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 (Schemes 2-7, Table 2). 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.
    Additional Material: 2 Tab.
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  • 5
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 561-568 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 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).
    Additional Material: 2 Ill.
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  • 6
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Second derivatives of the UV spectra of 2-(4-alkoxybenzyl)cyclopentan-1-ols and their acetates were used for the quantitative analysis of reaction kinetics of enzyme-mediated hydrolytic process. To determine the enantiomeric purity of the products using non-chiral HPLC columns, their diastereoisomeric esters of 3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid(MTPA) were prepared. The absolute configuration of the products was established using a combination of the results of a HPLC analysis and 1H/19F-NMR measurements of the diastereoisomeric MTP esters. The analytical method described consists of an easy routine HPLC analysis which can sometimes be used as a quick on-line analysis of the reaction kinetics and as a quick stepwise analysis of the optical purity and the absolute configuration of the products.
    Additional Material: 6 Ill.
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  • 7
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 81 (1998), S. 163-173 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The fate of an insect juvenile hormone analog applied to the insect body of the flesh fly (Sarcophaga bullata) or the tsetse fly (Glossina palpalis), respectively, was studied using three different radiolabeled positions in the parent biologically active compound 1. Several metabolites were found and analyzed. A mechanism of degradation of the applied molecule was designed using a combination of several radioanalytical methods. A unique monitoring of the applied compound and its metabolites was provided, based on the different radiolabeling of the structure (cf. 1a-1c), and established their fate in an insect body during a 10-day experiment. A 14C and 3H radiolabeling, respectively, was employed to synthesize three different radiolabeled forms 1a-1c derived from the parent non-labeled 1. A combination of three different ways of radiolabeling resulted in an advantage in tracing the metabolic pathway of degradation of the employed compound 1 in its radiolabeled forms 1a-1c.
    Additional Material: 2 Ill.
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  • 8
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 1091-1094 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 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 synthesis of 11a-14a. The structures of all compounds prepared (5,6,7a-14a, and 7b-10b) were determined spectroscopically, and the respective syn- and anti-isomers of the oxime ethers were identified. A brief survey of their biological activities shows that some of the compounds prepared possess higher activity against Musca domestica and/or Galleria mellonella species than does hydroprene.
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  • 9
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 847-852 
    ISSN: 0170-2041
    Keywords: Juvenoids ; Oxime ethers ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two racemic juvenoids 5 and 6 and their optical isomers 10, 11, 17 and 18 having chiral centres in the aliphatic side chain were synthetized. The second chiral centre in the molecules remained racemic in all derivatives prepared. The absolute configurations of the optically active centres of the enantiomers were determined on the basis of the 1H-NMR spectral evaluation of the diastereoisomeric MTPA esters 12, 13, 19 and 20 derived from the intermediate alcohols 8 and 15. The optical purity was established by an HPLC analysis of the corresponding MTPA esters. The 1H-NMR spectra of all compounds as well as the CD spectra of all chiral isomers were measured and discussed.
    Additional Material: 1 Ill.
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  • 10
    Publication Date: 2009-11-25
    Print ISSN: 0021-8561
    Electronic ISSN: 1520-5118
    Topics: Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition , Process Engineering, Biotechnology, Nutrition Technology
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