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Chemical Compound Review

Phenyl     cyclohexatriene

Synonyms: Phenyl radical, AC1L3VZC, AR-1L0506, FT-0614985, AC1Q1H6J
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Disease relevance of cyclohexatriene

  • Such a conformation is found for 7,8-benzoflavone with a torsion angle of 23 degrees between the phenyl group and the rest of the molecule [1].
  • Interestingly bacterial MAOs are no more closely related to PPOs, PHDs, and animal MAO's than they are to the unrelated Pseudomonas phenyl hydroxylase [2].
  • When tested for their effects on mucin glycosylation in a mucin-producing colon cancer cell line, LS174T, benzyl-, phenyl-, and p-nitrophenyl-N-acetyl-alpha-galactosaminide inhibited the formation of fully glycosylated mucin in a dose-dependent manner [3].
  • The unexpected finding was that phenyl Ox was also a (2.5-fold) more efficient challenge compound for mice that had been primed with propenyl Ox (a heteroclitic contact sensitivity) [4].
  • In addition to its known substrate activity with p-nitrophenyl beta-cellobioside, the exoglucanase from Cellulomonas fimi has been shown to utilize substituted phenyl beta-glucosides as substrates, of which the best is 2',4'-dinitrophenyl beta-D-glucopyranoside [5].

Psychiatry related information on cyclohexatriene


High impact information on cyclohexatriene


Chemical compound and disease context of cyclohexatriene

  • In E. coli R2 this channel is blocked by the phenyl ring of a tyrosine residue, which in mouse R2 is a serine [16].
  • Calculated and observed log P values are reported and compared with in vivo and in vitro biological action (L1210 leukemia ILS % and ribonucleotide reductase ID50) for hydroxyurea, the 1-N methyl and ethyl, and the 3-N ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, and p-chlorophenyl analogues [17].
  • The compound 2-amino-1-(isopropyl sulfonyl)-6-benzimidazole phenyl ketone oxime (LY122771-72) at a concentration of 0.2 microgram/ml completely inhibited rhinovirus replication in human embryonic nasal organ cultures, although in the absence of virus the compound did not inhibit ciliary activity when used at a concentration of 25 micrograms/ml [18].
  • In order to assess the orientation of the carbocyclic ring with respect to the phenyl group hydroxyl oxygen in each optimized structure, the following nonbonded torsion angles were measured: C10-C10a-C1-O, C8-C7-C1-O, C11-C9-C1-O, and C9-Q-C1-O (where Q is a dummy atom placed midway between C8 and C10).(ABSTRACT TRUNCATED AT 400 WORDS)[19]
  • A protease produced by a clinical isolate of Vibrio cholerae non-O1 was purified to apparent homogeneity by ammonium sulfate fractionation and successive column chromatography on DEAE-Sephadex A25, Sephadex G100, Mono Q, and Phenyl Superose [20].

Biological context of cyclohexatriene

  • These results indicate that change of the phenol side chains in the NPXY motifs to phenyl groups (which cannot be phosphorylated) has major effects on the organization of focal contacts and cytoskeleton and on directed cell motility [21].
  • In the presence of hormone-binding proteins, the phenyl radical thus formed, and possibly also the iodine radical, can establish a covalent bond with certain amino acid residues in the binding site [22].
  • The data also indicate formation of an oriented pi-complex involving phenyl participation (as contrasted with complete phenonium ion formation) in the alkylation intermediates of the beta-phenylethylation reactions [23].
  • Tyrosine phosphorylation of these proteins was increased as judged by immunoprecipitation of 32Pi-labeled cells and immunoblotting of unlabeled cells with monoclonal antiphosphotyrosine antibodies, elution with phenyl phosphate, and phospho amino acid analysis [24].
  • We have constructed and analyzed two derivatives of CAP: one having a phenyl azide photoactivatable crosslinking agent at amino acid 2 of the helix-turn-helix motif of CAP, and one having a phenyl azide photoactivatable crosslinking agent at amino acid 10 of the helix-turn-helix motif of CAP [25].

Anatomical context of cyclohexatriene

  • Zeolites, Nafion membranes, and microemulsions as microreactors remarkably control chemo-, regio-, and stereoselectivity in the photochemical reaction of phenyl phenylacetates, photocycloaddition of anthracenes, and photocyclization of azobenzene and stilbazole [26].
  • The high selectivity of phenyl ketone 1 for AKR1C2 over the many endogenous reductases present in mammalian cells was established by a quantitative comparison of the metabolic rates between null control cells (COS-1) and AKR1C2-transfected cells [27].
  • In vitro, NTE potently catalyses hydrolysis of phenyl valerate: however, its physiological substrate is likely to be a metabolite of a much longer chain carboxylic acid, possibly associated with cell membranes [28].
  • Mild chronic oxidative stress induced by hydrogen peroxide increased the rate of telomere shortening in A-T cells but not in normal fibroblasts and the telomere shortening rate decreased in both normal and A-T fibroblasts if cultures were supplemented with the anti-oxidant phenyl-butyl-nitrone [29].
  • Furamidine and its phenyl-substituted analogue that accumulate in the cell nuclei and mitochondria, respectively, share a common selectivity for AT sites and bind equally tightly to these sites [30].

Associations of cyclohexatriene with other chemical compounds

  • To test the role of peripheral olfactory receptors in odorant memory retention, we imprinted coho salmon (Oncorhynchus kisutch) to micromolar concentrations of phenyl ethyl alcohol during parr-smolt transformation [31].
  • The aromatic portion of the inhibitor binds to the adenine-binding pocket of CDK2, and the position of the phenyl group of the inhibitor enables the inhibitor to make contacts with the enzyme not observed in the ATP complex structure [32].
  • The analysis of the position of this phenyl ring not only explains the great differences of kinase inhibition among the flavonoid inhibitors but also explains the specificity of L868276 to inhibit CDK2 and CDC2 [32].
  • The protein that specifically binds 12-O-[3H]tetradecanoyl-phorbol-13-acetate was solubilized from mouse brain particulate protein with detergents and purified to apparent homogeneity by chromatograph on diethylaminoethyl-cellulose, hydroxylapatite, phenyl agarose, and gel filtration [33].
  • This is also the case for a guanidine derivative but not for the phenyl-substituted compound DB569, which essentially localizes in cytoplasmic granules [30].

Gene context of cyclohexatriene

  • The two additional phenyl and piperidyl ring substituents of the inhibitor bind into the S1' and S2' pockets of MMP-8, respectively [34].
  • Several retinoids and related synthetic compounds, including 13-cis RA, TTNPB, Ch55, Am80, and the trifluoromethyl nonyloxyphenyl analog of RA, also induced RAR beta mRNA, whereas a 24-h treatment with 10(-6) M retinol, TTNP (a decarboxylated analog of TTNPB), or the phenyl analog of RA failed to induce RAR beta mRNA [35].
  • Based on this study and on observations by other researchers, we postulate that P-glycoprotein-mediated resistance to paclitaxel could probably be eliminated by proper substitution of its benzamido and phenyl groups [36].
  • The CPP analogs with an ethyl, a phenyl, or an n-propyl group in place of the methyl group on the asymmetric center showed a scale of potency and a stereoselective behavior on ClC-1 similar to that observed for blocking gCl in native muscle fibers [37].
  • PON1 activity was monitored by the hydrolysis rate of paraoxon, diazoxon, and phenyl acetate [38].

Analytical, diagnostic and therapeutic context of cyclohexatriene


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