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Chemical Compound Review

Dibenzylether     phenylmethoxymethylbenzene

Synonyms: Plasticator BA, Plastikator BA, DIBENZYL ETHER, ETHER,DIBENZYL, SureCN27380, ...
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Disease relevance of benzyloxymethylbenzene


High impact information on benzyloxymethylbenzene

  • Facially amphiphilic biaryl dendrimers are compared with the more classical benzyl ether amphiphilic dendrimers for molecular recognition, using protein binding as the probe [2].
  • The two-photon ionization (TPI) process (308 and 266 nm) of stilbene dendrimers having a stilbene core and benzyl ether type dendrons has been investigated in an acetonitrile and 1,2-dichloroethane mixture (3:1) in order to elucidate the dendrimer effects [3].
  • In the particular case of isomers 4-cyanobenzyl phenyl ether and 4-cyanophenyl benzyl ether, the difference in intrinsic barriers amounts to 5.5 kcal/mol, and this produces an energetic crossing where the thermodynamically more favorable process (homolytic) is the kinetically slower one [4].
  • The synthesis and evaluation of analogues of previously reported farnesyltransferase inhibitors, pyridyl benzyl ether 3 and pyridylbenzylamine 4, are described [5].
  • Further structure-activity studies have now established that for high NK1 affinity the benzyl ether side chain must be 3,5-disubstituted and highly lipophilic, the optimal side chain being the 3, 5-bis(trifluoromethyl)benzyl ether, 12 (hNK1 IC50 = 0.95 nM) [6].

Biological context of benzyloxymethylbenzene


Anatomical context of benzyloxymethylbenzene

  • An asymmetric synthesis of 16-HETE, an endogenous inhibitor of neutrophil activity, was achieved in six steps from R-(-)-glycidyl benzyl ether in 28% overall yield [11].

Associations of benzyloxymethylbenzene with other chemical compounds


Gene context of benzyloxymethylbenzene


  1. Short term toxicity study in rats dosed with isoeugenol benzyl ether. Boe, M., Würtzen, G., Olsen, P. Drug and chemical toxicology. (1989) [Pubmed]
  2. Comparison of facially amphiphilic biaryl dendrimers with classical amphiphilic ones using protein surface recognition as the tool. Klaikherd, A., Sandanaraj, B.S., Vutukuri, D.R., Thayumanavan, S. J. Am. Chem. Soc. (2006) [Pubmed]
  3. Effects of benzyl ether type dendrons as hole-harvesting antennas, and shielding for the neutralization of stilbene core radical cations with chloride ion during two-photon ionization of stilbene dendrimers having stilbene core and benzyl ether type dendrons. Hara, M., Samori, S., Cai, X., Tojo, S., Arai, T., Momotake, A., Hayakawa, J., Uda, M., Kawai, K., Endo, M., Fujitsuka, M., Majima, T. J. Am. Chem. Soc. (2004) [Pubmed]
  4. Thermodynamics, kinetics, and dynamics of the two alternative aniomesolytic fragmentations of C-O bonds: an electrochemical and theoretical study. Pisano, L., Farriol, M., Asensio, X., Gallardo, I., González-Lafont, A., Lluch, J.M., Marquet, J. J. Am. Chem. Soc. (2002) [Pubmed]
  5. Second-generation peptidomimetic inhibitors of protein farnesyltransferase demonstrating improved cellular potency and significant in vivo efficacy. O'Connor, S.J., Barr, K.J., Wang, L., Sorensen, B.K., Tasker, A.S., Sham, H., Ng, S.C., Cohen, J., Devine, E., Cherian, S., Saeed, B., Zhang, H., Lee, J.Y., Warner, R., Tahir, S., Kovar, P., Ewing, P., Alder, J., Mitten, M., Leal, J., Marsh, K., Bauch, J., Hoffman, D.J., Sebti, S.M., Rosenberg, S.H. J. Med. Chem. (1999) [Pubmed]
  6. 4,4-Disubstituted piperidine high-affinity NK1 antagonists: structure-activity relationships and in vivo activity. Stevenson, G.I., Huscroft, I., MacLeod, A.M., Swain, C.J., Cascieri, M.A., Chicchi, G.G., Graham, M.I., Harrison, T., Kelleher, F.J., Kurtz, M., Ladduwahetty, T., Merchant, K.J., Metzger, J.M., MacIntyre, D.E., Sadowski, S., Sohal, B., Owens, A.P. J. Med. Chem. (1998) [Pubmed]
  7. Traceless Staudinger ligation of glycosyl azides with triaryl phosphines: stereoselective synthesis of glycosyl amides. Bianchi, A., Bernardi, A. J. Org. Chem. (2006) [Pubmed]
  8. Synthesis of di-branched heptasaccharide by one-pot glycosylation using seven independent building blocks. Tanaka, H., Adachi, M., Tsukamoto, H., Ikeda, T., Yamada, H., Takahashi, T. Org. Lett. (2002) [Pubmed]
  9. Identification of a novel factor, vanillyl benzyl ether, which inhibits somatic embryogenesis of Japanese larch (Larix leptolepis Gordon). Umehara, M., Ogita, S., Sasamoto, H., Koshino, H., Asami, T., Fujioka, S., Yoshida, S., Kamada, H. Plant Cell Physiol. (2005) [Pubmed]
  10. Benzyl ether structure-activity relationships in a series of ketopiperazine-based renin inhibitors. Powell, N.A., Clay, E.H., Holsworth, D.D., Bryant, J.W., Ryan, M.J., Jalaie, M., Edmunds, J.J. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  11. Practical, asymmetric synthesis of 16-hydroxyeicosa-5(Z),8(Z), 11(Z),14(Z)-tetraenoic acid (16-HETE), an endogenous inhibitor of neutrophil activity. Reddy, Y.K., Reddy, L.M., Capdevila, J.H., Falck, J.R. Bioorg. Med. Chem. Lett. (2003) [Pubmed]
  12. Wilkinson's catalyst catalyzed selective hydrogenation of olefin in the presence of an aromatic nitro function: a remarkable solvent effect. Jourdant, A., González-Zamora, E., Zhu, J. J. Org. Chem. (2002) [Pubmed]
  13. Safety evaluation of dibenzyl ether. Burdock, G.A., Ford, R.A. Food Chem. Toxicol. (1992) [Pubmed]
  14. Energy and charge transfer dynamics in fully decorated benzyl ether dendrimers and their disubstituted analogues. Ahn, T.S., Nantalaksakul, A., Dasari, R.R., Al-Kaysi, R.O., M??ller, A.M., Thayumanavan, S., Bardeen, C.J. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical (2006) [Pubmed]
  15. Improved anti-inflammatory activity of three new terpenoids derived, by systematic chemical modifications, from the abundant triterpenes of the flowery plant Calendula officinalis. Neukirch, H., D'Ambrosio, M., Sosa, S., Altinier, G., Della Loggia, R., Guerriero, A. Chem. Biodivers. (2005) [Pubmed]
  16. Synthesis and biological activity of selective pipecolic acid-based TNF-alpha converting enzyme (TACE) inhibitors. Letavic, M.A., Axt, M.Z., Barberia, J.T., Carty, T.J., Danley, D.E., Geoghegan, K.F., Halim, N.S., Hoth, L.R., Kamath, A.V., Laird, E.R., Lopresti-Morrow, L.L., McClure, K.F., Mitchell, P.G., Natarajan, V., Noe, M.C., Pandit, J., Reeves, L., Schulte, G.K., Snow, S.L., Sweeney, F.J., Tan, D.H., Yu, C.H. Bioorg. Med. Chem. Lett. (2002) [Pubmed]
  17. A remarkable solvent effect toward the Pd/C-catalyzed cleavage of silyl ethers. Sajiki, H., Ikawa, T., Hattori, K., Hirota, K. Chem. Commun. (Camb.) (2003) [Pubmed]
  18. 1-Phenyl-8-azabicyclo[3.2.1]octane ethers: a novel series of neurokinin (NK1) antagonists. Huscroft, I.T., Carlson, E.J., Chicchi, G.G., Kurtz, M.M., London, C., Raubo, P., Wheeldon, A., Kulagowski, J.J. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
  19. Novel histamine H3-receptor antagonists with benzyl ether structure or related moieties: synthesis and structure-activity relationships. Hüls, A., Purand, K., Stark, H., Reidemeister, S., Ligneau, X., Arrang, J.M., Schwartz, J.C., Schunack, W. Arch. Pharm. (Weinheim) (1996) [Pubmed]
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