The syntheses of biologically active 2-(4-hydroxybenzyl)-1-cyclohexanone derivatives

Wimmer, Zdeněk; Romaňuk, M.

doi:10.1135/cccc19812573

Cited by 20 publications

(8 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Likewise, the 7-isopropyl-4-methyl derivative 6e was prepared from (±)-menthone ( 3 , R = i -Pr, R‘ = Me); the synthesis commenced from Baeyer−Villiger oxidation. The species 3b , 3c , 3d , 4a , 6a , and 4e 16 exhibited known 1 H and IR spectral characteristics. The structures of all other intermediates were secured firmly from spectroscopic data and elemental analyses (vide infra).…”

Section: Starting Materialsmentioning

confidence: 98%

DBU-Catalyzed Deconjugation of 7-Substituted 3,4-Didehydro-2-oxepanones. Deuterium Incorporation, Significance of the Imine Double Bond, and Application to the Synthesis of a Key Pharmacophore

et al. 1998

View full text Add to dashboard Cite

7-Substituted 3,4-Didehydro-2-oxepanones are conveniently deconjugated to the 4,5-didehydro derivatives by DBU. The isomerization of 7-benzyl-substituted 2-oxepanones proceeds to the extent of 90% over the initial 3 h; the concentration falls gradually thereafter to achieve, in 25 h, a 3:2 equilibrium in favor of deconjugation. Such an equilibrium does not exist for the 7-methyl and the 7-(2-phenethyl) derivatives. The significance of the imine double bond in DBU has been explored. The isomerization in CDCl3 causes deuterium incorporation at positions 3 and 5 of the 2-oxepanones examined and at position 6 of DBU. The mechanistic rationales for these deuterium incorporations are advanced. The transformation of 7-benzyl-3,4-didehydro-2-oxepanone into a bicyclo[3.3.0] skeleton that is present in a diverse class of biologically active natural products is described as a possible potential use of the present deconjugation methodology.

show abstract

Section: Starting Materialsmentioning

confidence: 98%

DBU-Catalyzed Deconjugation of 7-Substituted 3,4-Didehydro-2-oxepanones. Deuterium Incorporation, Significance of the Imine Double Bond, and Application to the Synthesis of a Key Pharmacophore

et al. 1998

View full text Add to dashboard Cite

show abstract

“…The first structural type consists of a series of α, β‐unsaturated esteric juvenoids [the ( E )‐isomers] (Fig. 1a), bearing hydroxyl functionality at the 1,2‐disubstituted cyclohexane ring, which results in synthesis and separation of the cis ‐ and trans ‐isomers of the alcoholic juvenoids ( 1 and 2 ) 28. The alcoholic juvenoids were transformed into their alkyl β‐ D ‐glucopyranoside derivatives ( 3 and 4 )18 and β‐ D ‐galactopyranoside derivatives ( 5 and 6 ) 29.…”

Section: Methodsmentioning

confidence: 99%

“…By 1975, several series of aliphatic juvenoid compounds had been prepared and their biological effects investigated at the Institute of Organic Chemistry and Biochemistry (IOCB) in Prague 11, 12. In the search for more stable compounds, attention was focused on derivatives of 2‐(4‐hydroxybenzyl)cyclohexanone 13. Similarly, in commercially available juvenoids, increased metabolic and environmental stability was obtained with successive replacement of isoprene units by aromatic rings (e.g.…”

Section: Introductionmentioning

confidence: 99%

The systemic effects of juvenoids on the red firebug Pyrrhocoris apterus and on the pea aphid Acyrthosiphon pisum with data on life table response

Jedlička

Kuldová

Wimmer

2007

Pest Management Science

Self Cite

View full text Add to dashboard Cite

Expected systemic activity of glycosidic juvenogens in P. apterus was not confirmed by exposure of the pea aphid on broad bean treated with aqueous solutions of the compounds. Nevertheless, the carbamate juvenoid alcohol 8 displayed a considerable juvenilizing effect on A. pisum in screening tests. Furthermore, this compound indicated a sublethal effect as the realized fecundity U(x) decreased disproportionately to the age-specific survival L(x) with increased concentration. The population parameters are compared with the data in similar demographic studies and are discussed together with the possibilities of using the compounds of this structural type in practice.

show abstract

“…Unfortunately, the rewards, uncommon for the communist bloc, of bi-lateral American-Czechoslovak cooperation was suddenly discontinued in 1980 for political reasons. Since then, the research on JH analogues has greatly decreased (Wimmer & Romaňuk, 1981;Sehnal, 1982Sehnal, , 1984Sláma, 1985Sláma, , 1999Wimmer et al, 1997) and ambitious projects discontinued.…”

Section: Final Considerationsmentioning

confidence: 99%

A new look at the nature of insect juvenile hormone with particular reference to studies carried out in the Czech Republic

Sláma¹

2015

Eur. J. Entomol.

View full text Add to dashboard Cite

This article is a comprehensive summary of the 50-year history of physiological investigations in the Czech Republic into the mode of action of the corpus allatum hormone (CAH) in insects, which is commonly known as the juvenile hormone (JH). During this period 4000 synthetic JH-mimetic bioanalogues were tested. The sesquiterpenoid epoxy-homofarnesoate (JH-I), which is generally thought to be the true JH of insects, is an excretory product of the male colleterial gland, not an insect hormone. There are two principal hormones produced by the insect neuroendocrine system: activation hormone (AH) produced by neurosecretory cells in the brain and JH secreted by the corpora allata. The prothoracic glands are a subordinated target of JH, not PTTH; they are not involved in the regulation of moulting in insects. The development of larval, pupal and adult structures depends primarily on inherited instructions encoded within the genome, not on high, medium or low concentrations of JH. At the level of epidermal cells, the responses to JH are always "all-or-none" with intermediate forms mosaic mixtures of cells of previous and future developmental stages. There are two alternative theorical explanations of the action of insect hormones. The Gilbert-Riddiford theory proposes that insect development is stimulated by a moulting hormone (ecdysone) released from the PG in response to the prothoracicotropic hormone (PTTH) from the brain. Formation of larval, pupal and adult epidermal strucures depends, respectively, on high, medium or low concentrations of JH. The alternative hormonal theory of Novák-Sláma argues that PG is not involved in the regulation of insect moults. High, medium or low concentrations of JH have nothing in common with the selective formation of larval, pupal or adult structural characters. The immature stages of certain insect groups undergo an autonomic (hormone independent), genetically programmed morphogenesis, which can be extended over several moulting cycles. Comparative endocrinological studies revealed several common evolutionary links between the neuroendocrine systems of insects and humans. The neurosecretory cells (NSC) in the insect brain and the NSC in the human hypothalamus are homologous as are the neurohaemal organs (CC) in insects and the neurohypophysis in humans, and the glandular CA in insects is anatomically and physiologically homologous with the human adenohypophysis. The centrally produced hormones (AH and CAH) alter the transcriptional potential the cellular genome. AH switches on genes at the most suitable moments for initiating inherited developmental programmes; JH determines in which direction the development should proceed, i.e. larval somatic growth or morphogenesis.

show abstract

The syntheses of biologically active 2-(4-hydroxybenzyl)-1-cyclohexanone derivatives

Abstract: The syntheses of various 2-(4-hydroxybenzyl)-1-cyclohexanone derivatives are described in connection with the development of the research of substances with juvenile hormone activity.

Cited by 20 publications

References 0 publications

DBU-Catalyzed Deconjugation of 7-Substituted 3,4-Didehydro-2-oxepanones. Deuterium Incorporation, Significance of the Imine Double Bond, and Application to the Synthesis of a Key Pharmacophore

DBU-Catalyzed Deconjugation of 7-Substituted 3,4-Didehydro-2-oxepanones. Deuterium Incorporation, Significance of the Imine Double Bond, and Application to the Synthesis of a Key Pharmacophore

The systemic effects of juvenoids on the red firebug Pyrrhocoris apterus and on the pea aphid Acyrthosiphon pisum with data on life table response

A new look at the nature of insect juvenile hormone with particular reference to studies carried out in the Czech Republic

Contact Info

Product

Resources

About