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Chemical Compound Review

CYCLOHEXADIENE     cyclohexa-1,3-diene

Synonyms: AG-E-97204, ACMC-209ytb, CHEBI:37610, ANW-49389, AC1L1XPU, ...
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Disease relevance of CYCLOHEXADIENE

  • In the rat acute subdural haematoma model, both the triazole and cyclohexadiene displayed reduction of brain water content (-26% at 0.3 mg/kg and -24% at 0.01 mg/kg) and reduction of the intracranial pressure (-46% at 0.1 mg/kg and -60% at 0.003 mg/kg) after 24 h when administered as a 4-h infusion immediately after brain injury [1].

High impact information on CYCLOHEXADIENE

  • Besides decreasing the extent of cyclohexa-1,3-diene disproportionation at palladium, the combined action of the two metals activates the arene so as to allow the rhodium sites to enter the catalytic cycle and speed up the overall hydrogenation process by rapidly reducing benzene to cyclohexa-1,3-diene [2].
  • The initial addition reaction follows a stepwise diradical pathway to form cyclohexadiene endoperoxide with an activation barrier of 6.5 kcal/mol (standard level = CASPT2(12e,10o)/6-31G(d); geometries and zero-point corrections at B3LYP/6-31G(d)), which is consistent with an experimental value of 5.5 kcal/mol [3].
  • The ground- (S0) and lowest triplet-state (T1) pathways associated with dimerization of cyclohexadiene to give [2+2] and [4+2] cycloadducts have been theoretically studied at the UBLYP and UB3LYP levels of theory with the 6-31G* basis set [4].
  • The absolute stereospecificity of the ring and side-chain hydroxylations of the DbetaM/CHDEA reaction suggests that the side-chain pro-R hydrogen of the enzyme-bound substrate is close to perpendicular to the aromatic ring of the phenylethylamine substrate or cyclohexadiene ring of CHDEA [5].
  • Compared with known KCNN4 blockers, such as clotrimazole (IC50=360 +/- 12 nm) and charybdotoxin (IC50=3.3 +/- 1.9 nm), the triazole and cyclohexadiene were considerably more potent than clotrimazole and displayed similar potencies (IC50=12.1 +/- 8.8 and 13.3 +/- 4.7 nm, respectively) [1].

Biological context of CYCLOHEXADIENE


Anatomical context of CYCLOHEXADIENE


Associations of CYCLOHEXADIENE with other chemical compounds


Gene context of CYCLOHEXADIENE


Analytical, diagnostic and therapeutic context of CYCLOHEXADIENE


  1. Selective intermediate-/small-conductance calcium-activated potassium channel (KCNN4) blockers are potent and effective therapeutics in experimental brain oedema and traumatic brain injury caused by acute subdural haematoma. Mauler, F., Hinz, V., Horváth, E., Schuhmacher, J., Hofmann, H.A., Wirtz, S., Hahn, M.G., Urbahns, K. Eur. J. Neurosci. (2004) [Pubmed]
  2. Hydrogenation of arenes over silica-supported catalysts that combine a grafted rhodium complex and palladium nanoparticles: evidence for substrate activation on Rh(single-site)-Pd(metal) moieties. Barbaro, P., Bianchini, C., Dal Santo, V., Meli, A., Moneti, S., Psaro, R., Scaffidi, A., Sordelli, L., Vizza, F. J. Am. Chem. Soc. (2006) [Pubmed]
  3. Reactions of 1,3-cyclohexadiene with singlet oxygen. A theoretical study. Sevin, F., McKee, M.L. J. Am. Chem. Soc. (2001) [Pubmed]
  4. Exploring two-state reaction pathways in the photodimerization of cyclohexadiene. Domingo, L.R., Pérez-Prieto, J. Chemphyschem : a European journal of chemical physics and physical chemistry. (2006) [Pubmed]
  5. Mode of substrate interaction and energetics of carbon-oxygen bond formation of the dopamine beta-monooxygenase reaction. Wimalasena, K., Alliston, K.R. Biochemistry (1999) [Pubmed]
  6. Kinetics study and theoretical modeling of the Diels-Alder reactions of cyclopentadiene and cyclohexadiene with methyl vinyl ketone. The effects of a novel organotungsten catalyst. Fu, Y.S., Tsai, S.C., Huang, C.H., Yen, S.Y., Hu, W.P., Yu, S.J. J. Org. Chem. (2003) [Pubmed]
  7. Metabolism of 1,3-cyclohexadiene by isolated rat liver cells. Lippi, A., Citti, L., Gervasi, P., Turchi, G., Bellucci, G., Mastrorilli, E. Toxicology (1983) [Pubmed]
  8. Metal complexes with 2,3-bis(diphenylphosphino)-1,4-diazadiene ligands: synthesis, structures, and an intramolecular metal-mediated [4 + 2] cycloaddition employing a benzene ring as a dienophile. Walther, D., Liesicke, S., Böttcher, L., Fischer, R., Görls, H., Vaughan, G. Inorganic chemistry. (2003) [Pubmed]
  9. Photochemistry of 2-hydroxy-4-trifluoromethylbenzoic acid, major metabolite of the photosensitizing platelet antiaggregant drug triflusal. Boscá, F., Cuquerella, M.C., Marín, M.L., Miranda, M.A. Photochem. Photobiol. (2001) [Pubmed]
  10. Rearrangement of 5S, 12S-dihydroxy-6,8,10,14-(E,Z,E,Z)-eicosatetraenoic acid during gas chromatography: formation of a cyclohexadiene derivative. Borgeat, P., Pilote, S. Prostaglandins (1988) [Pubmed]
  11. The metabolism of 1,3-cyclohexadiene by liver microsomal mono-oxygenase. Gervasi, P.G., Citti, L., Turchi, G., Bellucci, G., Berti, G., Mastrorilli, E., Tortello, M.P. Xenobiotica (1982) [Pubmed]
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