Disease relevance of cyclohexene

• The binding of both cyclohexene nucleosides in the active site of HSV-1 thymidine kinase was investigated, and a model for the binding of both enantiomers is proposed [1].
• Breaks induced in the deoxyribonucleic acid of aerosolized Escherichia coli by ozonized cyclohexene [2].
• Short-term inhalation studies of EVK were conducted to provide toxicity data for comparison with the related alpha,beta-unsaturated ketones 2-cyclohexene-1-one (CHX) and methyl vinyl ketone (MVK) [3].
• Biosynthesis of ansatrienin by Streptomyces collinus: cell-free transformations of cyclohexene- and cyclohexadienecarboxylic acids [4].
• In contrast, the DNA from phage phiX174 inactivated by ozonized cyclohexene is broken [5].

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

• No alteration of small ovarian follicle counts occurred following treatment with structural analogues of VCH (vinylcyclohexane, ethylcyclohexene, and cyclohexene) that contain only a single unsaturated site [18].
• Hydroxylation of cyclohexene at the allylic position has been shown to occur in hepatic microsomes and 9000 g supernatant fractions of rats and rabbits [19].

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].

References