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Chemical Compound Review

Zyklohexen     cyclohexene

Synonyms: cyclohexen, CYCLOHEXENE, Cykloheksen, Cyclohex-1-ene, CHEMBL16396, ...
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Disease relevance of cyclohexene


Psychiatry related information on cyclohexene

  • The chlorinated cyclohexene derivatives limit the quantitative and qualitative analysis of compounds eluting at Kovát's index less than 700-1000 and the use of these extracts for organoleptic and mutagenic studies [6].

High impact information on cyclohexene

  • Of particular interest, however, the T303A mutation of P450 2E1 resulted in enhanced epoxidation of all of the model olefins along with decreased allylic hydroxylation of cyclohexene and butene [7].
  • In order to prepare a completely light-stable rhodopsin, we have synthesized an analog, II, of 11-cis retinal in which isomerization at the C11-C12 cis-double bond is blocked by formation of a cyclohexene ring from the C10 to C13-methyl [8].
  • In contrast, analogous poisoning effects were not detected for the catalytic hydrogenation of cyclohexene using Rh/Al2O3 or the Pd-catalyzed Suzuki cross-coupling of PhB(OH)2 and PhI [9].
  • However, the same methods reveal that the cyclohexene hydrogenation catalyst derived from 1 at the milder conditions of 22 degrees C and 3.7 atm H2 is a nonnanocluster, homogeneous catalyst, most likely the previously identified complex, [Rh(eta5-C5Me5)(H)2(solvent)] (Gill, D. S.; White, C.; Maitlis, P. M J. C. S. Dalton Trans. 1978, 617) [10].
  • Kinetic analyses of cyclohexene epoxidation confirmed that the active sites were anchored on the silica surface and were significantly more active than their homogeneous analogues [11].

Chemical compound and disease context of cyclohexene

  • Because these epoxides have never been isolated or synthesized for direct evaluation of their toxicity we have determined the toxicity toward isolated rat hepatocytes of a series of cyclohexene and cyclohexadiene derivatives containing epoxide and/or alpha, beta-unsaturated nitrile functional groups [12].

Biological context of cyclohexene

  • In order to probe important structure-activity relationships, we evaluated a homologous series of four 6-s-trans-retinoids that are 8-(2'-cyclohexen-1'-ylidene)-3,7-dimethyl-2,4,6-octatrienoic acids with different substituents at 2' (R2) and 3' (R1) positions on the cyclohexene ring [13].
  • Diastereoselective double Heck cyclizations of cyclohexene diamides 1 and 3 form contiguous quaternary stereocenters, with diastereoselection being controlled by the trans-diol protecting group [14].
  • The cyclohexene and cyclopentene analogs, 3-hydroxycyclohex-1-enecarboxylic acid [(RS)-HOCHCA] and 3-hydroxycyclopent-1-enecarboxylic acid [(RS)-HOCPCA], were found to be high-affinity GHB ligands, with IC50 values in the nanomolar range, and had 9 and 27 times, respectively, higher affinity than GHB [15].
  • Optically active cyclohexene derivative as a new antisepsis agent: an efficient synthesis of ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate (TAK-242) [16].
  • SAR studies to replace the cyclohexene-linker of FR181157 led to the discovery of compound 1i (FR207845) as a potent non-prostanoid PGI2 mimetic with good oral bioavailability [17].

Anatomical context of cyclohexene


Associations of cyclohexene with other chemical compounds

  • The metabolism of benzoate, cyclohex-1-ene carboxylate, and cyclohexane carboxylate by "Syntrophus aciditrophicus" in cocultures with hydrogen-using microorganisms was studied [20].
  • Early molecular modeling studies with Delta9-tetrahydrocannabinol (Delta9-THC) reported that three discrete regions which interact with brain cannabinoid (CB1) receptors corresponded to the C-9 position of the cyclohexene ring, the phenolic hydroxyl and the carbon side chain at the C3 position [21].
  • A thermosensitive nanocatalyst was prepared in the reaction of water-soluble iron(III) porphyrins and thermosensitive polymeric nanospheres with a core-shell structure; its catalytic activity in cyclohexene oxidation by iodosylbenzene was dependent markedly on reaction temperatures in aqueous solution [22].
  • [structure: see text] Fifteen novel dimeric amide alkaloids possessing a cyclohexene ring, nigramides A-O (1-15), as well as four novel dimeric amide alkaloids possessing a cyclobutane ring, nigramides P-S (17-20), have been isolated from the roots of Piper nigrum [23].
  • Cross-reactions between cumene hydroperoxide and cyclohexene hydroperoxide show that similarity in the overall structure and the way of antigen formation are needed [24].

Gene context of cyclohexene

  • A novel cyclohexene derivative, ethyl (6R)-6-[N-(2-Chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate (TAK-242), selectively inhibits toll-like receptor 4-mediated cytokine production through suppression of intracellular signaling [25].
  • A series of influenza neuraminidase inhibitors with the cyclohexene scaffold containing lipophilic side chains have been synthesized and evaluated for influenza A and B neuraminidase inhibitory activity [26].
  • The lowest energy structure contains a half chair-type cyclohexene A ring, while two structures whose energies are approximately 3-4 kcal/mol higher are boat-type [27].
  • A highly stereospecific retro-Diels-Alder process was observed in the cyclohexene-fused isomers under the EI conditions, and a corresponding (although less specific) fragmentation was observed in their FAB spectra [28].
  • The proposed mechanism for formation of cyclohexene cation in the gas phase is analogous to that determined for this process under matrix isolation conditions, where it proceeds via a Cope rearrangement to the cyclohexane-1,4-diyl cation, followed by isomerization to cyclohexene cation [29].

Analytical, diagnostic and therapeutic context of cyclohexene

  • Moreover, adducts isolated from the plant and cell culture showed not only a different cyclohexene ring substitution but also a different stereochemistry, that was found CIS-TRONS in the metabolites isolated from callus, and TRANS-TRANS in those isolated from the root bark [30].


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  8. Light-stable rhodopsin. II. An opsin mutant (TRP-265----Phe) and a retinal analog with a nonisomerizable 11-cis configuration form a photostable chromophore. Ridge, K.D., Bhattacharya, S., Nakayama, T.A., Khorana, H.G. J. Biol. Chem. (1992) [Pubmed]
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  10. Is it homogeneous or heterogeneous catalysis? Compelling evidence for both types of catalysts derived from [Rh(eta5-C5Me5)Cl2]2 as a function of temperature and hydrogen pressure. Hagen, C.M., Widegren, J.A., Maitlis, P.M., Finke, R.G. J. Am. Chem. Soc. (2005) [Pubmed]
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  14. Diastereoselection in the formation of spirocyclic oxindoles by the intramolecular heck reaction. Overman, L.E., Watson, D.A. J. Org. Chem. (2006) [Pubmed]
  15. Novel cyclic gamma-hydroxybutyrate (GHB) analogs with high affinity and stereoselectivity of binding to GHB sites in rat brain. Wellendorph, P., Høg, S., Greenwood, J.R., de Lichtenberg, A., Nielsen, B., Frølund, B., Brehm, L., Clausen, R.P., Bräuner-Osborne, H. J. Pharmacol. Exp. Ther. (2005) [Pubmed]
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  19. Microsomal metabolism of cyclohexene. Hydroxylation in the allylic position. Leibman, K.C., Ortiz, E. Drug Metab. Dispos. (1978) [Pubmed]
  20. Metabolism of benzoate, cyclohex-1-ene carboxylate, and cyclohexane carboxylate by "Syntrophus aciditrophicus" strain SB in syntrophic association with H(2)-using microorganisms. Elshahed, M.S., Bhupathiraju, V.K., Wofford, N.Q., Nanny, M.A., McInerney, M.J. Appl. Environ. Microbiol. (2001) [Pubmed]
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  25. A novel cyclohexene derivative, ethyl (6R)-6-[N-(2-Chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate (TAK-242), selectively inhibits toll-like receptor 4-mediated cytokine production through suppression of intracellular signaling. Ii, M., Matsunaga, N., Hazeki, K., Nakamura, K., Takashima, K., Seya, T., Hazeki, O., Kitazaki, T., Iizawa, Y. Mol. Pharmacol. (2006) [Pubmed]
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