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Chemical Compound Review

Bibenzoyl     1,2-diphenylethane-1,2-dione

Synonyms: Dibenzoyl, BENZIL, SureCN66, B5151_ALDRICH, CHEMBL189886, ...
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Disease relevance of benzil


High impact information on benzil

  • 3D-QSAR analyses of these benzil analogues for three different mammalian CEs demonstrated excellent correlations of observed versus predicted K(i) (r(2) > 0.91), with cross-validation coefficients (q(2)) of 0 [5].
  • Benzil and 30 analogues demonstrated selective inhibition of CEs, with no inhibitory activity toward human acetylcholinesterase or butyrylcholinesterase [5].
  • 1,4-Dimethylputrescine (2,5-hexanediamine) was separated into its racemic and meso isomers by fractional crystallization of its dibenzoyl derivative [6].
  • The addition of water brings about an increase in the dimerization rate constant and an associated increase in the amount of benzil that is produced [7].
  • The benzil concentration, which is approximately 6.2 mol/L in the neat crystals, varies between 1.01 and 1.51 mol/L in the structures studied, corresponding to a 6-fold dilution [8].

Biological context of benzil

  • Other important steps are the highly stereoselective Pd-catalyzed Heck cyclization of N-methylanilide 23a which led to the desired spiro-oxindole 24a, the fully regioselective intramolecular oxymercuration of 25a to the desired cyclic ether, and the remarkable oxindole N-demethylation of 29 via a radical mechanism by using dibenzoyl peroxide [9].
  • Thus, this clone seemed to carry a plasmid encoding a Bacillus cereus benzil reductase [2].
  • Finally, efficient triplet-triplet energy transfer from the benzil-doped polymer to the red-emitting phosphorescent dye Pt(II)octaethylporphyrin is established [10].
  • The cytoplasmic acidophilia of degenerating hippocampal neurons was due to a protein rich in lysine (extinguished by alkalinity, easily prevented by deamination, and unaffected by benzil) [11].
  • Atmospheric pressure chemical ionization in negative ion mode and selected ion monitoring method were developed to determine [M](-) at 186 and 210 for chimaphilin and benzil (internal standard), respectively [12].

Anatomical context of benzil


Associations of benzil with other chemical compounds


Gene context of benzil

  • Asymmetric reduction with B. cereus benzil reductase, yeast YIR036C protein and gerbil sepiapterin reductase will be utilized to produce important chiral compounds [3].
  • Benzil, a potent activator of microsomal epoxide hydrolase in vitro [17].
  • The method developed uses a reversed phase C18 column for the separation of MX derivatives, an internal standard benzil for method calibration, and a UV detector at a wavelength of 310 nm for analyte detection [19].
  • The catalytic activity of immobilized catalase (EC for two model peroxide compounds (dibenzoyl peroxide and 3-chloroperoxibenzoic acid) in a non-aqueous medium was used to prepare an organic-phase enzyme electrode (OPEE) [20].
  • Two phenylated compounds of methylglyoxal bis(guanylhydrazone), potentially inhibitors of diamine oxidase activity, have been synthesized: phenylglyoxal bis(guanylhydrazone) and diphenylglyoxal bis(guanylhydrazone) [21].

Analytical, diagnostic and therapeutic context of benzil

  • The structure of 1 was established by analysis of spectroscopic data, including absolute stereochemistry determined by circular dichroism analysis of the dibenzoyl derivative 2 [22].
  • Radial immunodiffusion revealed similar changes in the amount of enzyme protein present, except for two cases, where the increase in amount was larger; and the enzyme seems to be inhibited by benzil [23].


  1. Structural insights into drug processing by human carboxylesterase 1: tamoxifen, mevastatin, and inhibition by benzil. Fleming, C.D., Bencharit, S., Edwards, C.C., Hyatt, J.L., Tsurkan, L., Bai, F., Fraga, C., Morton, C.L., Howard-Williams, E.L., Potter, P.M., Redinbo, M.R. J. Mol. Biol. (2005) [Pubmed]
  2. Isolation and expression of a Bacillus cereus gene encoding benzil reductase. Maruyama, R., Nishizawa, M., Itoi, Y., Ito, S., Inoue, M. Biotechnol. Bioeng. (2001) [Pubmed]
  3. The enzymes with benzil reductase activity conserved from bacteria to mammals. Maruyama, R., Nishizawa, M., Itoi, Y., Ito, S., Inoue, M. J. Biotechnol. (2002) [Pubmed]
  4. Intracellular inhibition of carboxylesterases by benzil: modulation of CPT-11 cytotoxicity. Hyatt, J.L., Tsurkan, L., Wierdl, M., Edwards, C.C., Danks, M.K., Potter, P.M. Mol. Cancer Ther. (2006) [Pubmed]
  5. Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. Wadkins, R.M., Hyatt, J.L., Wei, X., Yoon, K.J., Wierdl, M., Edwards, C.C., Morton, C.L., Obenauer, J.C., Damodaran, K., Beroza, P., Danks, M.K., Potter, P.M. J. Med. Chem. (2005) [Pubmed]
  6. Inhibition of ornithine decarboxylase by the isomers of 1,4-dimethylputrescine. Moyano, N., Frydman, J., Buldain, G., Ruiz, O., Frydman, R.B. J. Med. Chem. (1990) [Pubmed]
  7. Quantitative evaluation of the mechanism of electroreduction of benzoyl cyanides. Macías-Ruvalcaba, N.A., Evans, D.H. J. Org. Chem. (2007) [Pubmed]
  8. Multiple conformations of benzil in resorcinarene-based supramolecular host matrixes. Ma, B.Q., Zhang, Y., Coppens, P. J. Org. Chem. (2003) [Pubmed]
  9. First total synthesis of ent-gelsedine via a novel iodide-promoted allene N-acyliminium ion cyclization. Beyersbergen van Henegouwen, W.G., Fieseler, R.M., Rutjes, F.P., Hiemstra, H. J. Org. Chem. (2000) [Pubmed]
  10. Sensitized phosphorescence of benzil-doped ladder-type methyl-poly(para-phenylene). Bagnich, S.A., Bässler, H., Neher, D. The Journal of chemical physics. (2004) [Pubmed]
  11. A histochemical examination of the staining of kainate-induced neuronal degeneration by anionic dyes. Kiernan, J.A., Macpherson, C.M., Price, A., Sun, T. Biotechnic & histochemistry : official publication of the Biological Stain Commission. (1998) [Pubmed]
  12. LC-MS Method for Determination and Pharmacokinetic Study of Chimaphilin in Rat Plasma after Oral Administration of the Traditional Chinese Medicinal Preparation Lu Xian Cao Decoction. Zhang, Y., Chen, X., Qin, S., Kim, C., Tebayashi, S., Bia, K. Biol. Pharm. Bull. (2006) [Pubmed]
  13. Arginine-rich proteins in spherical inclusions of human locus coeruleus neurons demonstrated by benzil modification. Panayotacopoulou, M.T., Issidorides, M.R. J. Histochem. Cytochem. (1984) [Pubmed]
  14. The effects of metyrapone, chalcone epoxide, benzil, clotrimazole and related compounds on the activity of microsomal epoxide hydrolase in situ, in purified form and in reconstituted systems towards different substrates. Seidegård, J., DePierre, J.W., Guenthner, T.M., Oesch, F. Eur. J. Biochem. (1986) [Pubmed]
  15. The effect of camphorquinone (CQ) and CQ-related photosensitizers on the generation of reactive oxygen species and the production of oxidative DNA damage. Pagoria, D., Lee, A., Geurtsen, W. Biomaterials (2005) [Pubmed]
  16. Oxygen uptake and involvement of superoxide radicals upon photolysis of ketones in air-saturated aqueous alcohol, formate, amine or ascorbic acid solutions. Görner, H. Photochem. Photobiol. (2006) [Pubmed]
  17. Benzil, a potent activator of microsomal epoxide hydrolase in vitro. Seidegård, J., DePierre, J.W. Eur. J. Biochem. (1980) [Pubmed]
  18. A benzil and isoflavone derivatives from Derris scandens Benth. Mahabusarakam, W., Deachathai, S., Phongpaichit, S., Jansakul, C., Taylor, W.C. Phytochemistry (2004) [Pubmed]
  19. Development and validation of an HPLC-UV method for the analysis of methoxyamine using 4-(diethylamino)benzaldehyde as a derivatizing agent. Liao, Y.C., Yang, S., Syu, M.J., Xu, Y. Journal of pharmaceutical and biomedical analysis. (2005) [Pubmed]
  20. Study of catalase electrode for organic peroxides assays. Horozova, E., Dimcheva, N., Jordanova, Z. Bioelectrochemistry (Amsterdam, Netherlands) (2002) [Pubmed]
  21. Effects of phenylated compounds of methylglyoxal bis(guanylhydrazone) on diamine oxidase activity from rat small intestine. Balaña-Fouce, R., Pulido, T.G., Escudero, D.O., Sanz-Sanchez, F. Comp. Biochem. Physiol. C, Comp. Pharmacol. Toxicol. (1986) [Pubmed]
  22. (2S,3R)-2-aminododecan-3-ol, a new antifungal agent from the ascidian Clavelina oblonga. Kossuga, M.H., MacMillan, J.B., Rogers, E.W., Molinski, T.F., Nascimento, G.G., Rocha, R.M., Berlinck, R.G. J. Nat. Prod. (2004) [Pubmed]
  23. Hepatic levels of cytosolic, microsomal and 'mitochondrial' epoxide hydrolases and other drug-metabolizing enzymes after treatment of mice with various xenobiotics and endogenous compounds. Meijer, J., DePierre, J.W. Chem. Biol. Interact. (1987) [Pubmed]
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