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Chemical Compound Review

BIBENZYL     phenethylbenzene

Synonyms: Dibenzil, Dibenzyl, DIPHENYLETHANE, PubChem7518, CHEMBL440895, ...
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Disease relevance of phenethylbenzene


High impact information on phenethylbenzene

  • 5-Substituted chroman analogues such as the caffeic acid amides 12 and 16 and the dihydrostilbene analogue 24 were the most potent against both H(2)O(2)- and glutamate-induced damage in Jurkat T cells and HT22 cells, respectively [6].
  • The 1,2-diphenylethane pharmacophor, however, cannot adapt an antiperiplanar conformation to interact with the estrogen receptor (ER) comparable to synthetic (e.g., diethylstilbestrol (DES)) or steroidal (e.g., estradiol (E2)) estrogens [7].
  • The algorithms presented here are used to perform nonlinear least-squares analyses of ST-EPR spectra of the anion exchange protein of the human erythrocyte membrane, band 3, which has been affinity spin-labeled with a recently developed dihydrostilbene disulfonate derivative, [15N,2H13]-SL-H2DADS-MAL [8].
  • Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization [9].
  • Within the series, dibenzyl analogues (R = benzyl) were found to be the most effective growth inhibitors, with IC50 values of about 10(-6) M [10].

Chemical compound and disease context of phenethylbenzene


Biological context of phenethylbenzene

  • Protonated dibenzyl ether loses formaldehyde upon dealkylation, via an ion-neutral complex of the benzyloxymethyl cation and neutral benzene [11].
  • A simple method was developed for preparation of trans-3'-hydroxycotinine from cotinine in two steps by using NaN[(CH3)3Si]2 and dibenzyl peroxydicarbonate, followed by base-catalyzed hydrolysis [12].
  • The phosphorylation step was found to be considerably improved using in situ-generated dibenzyl chlorophosphite [13].
  • Dibenzyl bromophenols with diverse dimerization patterns from the brown alga Leathesia nana [14].
  • Benzylation of the nitrile took place on the alpha-carbon to the cyano group preferentially affording the corresponding mono- and dibenzyl derivative, whose reductive cyclization resulted in 7-benzyl-5H-pyrrolo[3,2-d]pyrimidine-2,4-diamine and 7,7-dibenzyl-7H-pyrrolo[3,2-d]pyrimidine-2,4,6-triamine, respectively [15].

Anatomical context of phenethylbenzene

  • Only the dibenzyl derivative was slightly affected by sodium, suggesting a dual action for this peptide, as confirmed by preliminary data from guinea pig ileum bioassay [16].
  • Pharmacological data indicated that the strongest anticholinergic activity was shown by the dibenzyl amine 4 g, which among the tested molecules presented also a rather potent effect at the ganglia level, resulting about three times more potent than hexamethonium as ganglionic blocking agent [17].

Associations of phenethylbenzene with other chemical compounds

  • For benzophenones, acetophenones, and dibenzyl ether, which are all preferentially protonated at the oxygen, deacylation or dealkylation was observed in the collision-induced dissociation of the protonated molecules [11].
  • EPR investigation of persistent radicals produced from the photolysis of dibenzyl ketones adsorbed on ZSM-5 zeolites [18].
  • Selective protection (tetraacetate 4) of (+)-pancratistatin (la) was followed by phosphorylation (to 5) with dibenzyl chlorophosphite (prepared in situ from dibenzyl phosphite) [19].
  • Diethyl ester and dibenzyl ester derivatives of the inhibitor were active against cathepsin L and the plasmodial protease falcipain 2, but only the latter displayed potent antiplasmodial activity against viable parasites [20].
  • A new furofuran lignan, styraxlignolide B (1), and four new dibenzyl-gamma-butyrolactone lignans, styraxlignolides C-F (2-5), were isolated from the EtOAc-soluble fraction of stem bark of Styrax japonica [21].

Gene context of phenethylbenzene

  • However, they showed weak antagonist activity at each receptor subtype, with the exception of the dibenzyl analogue, which was a potent and selective NK-1 receptor antagonist [22].
  • Moreover, dibenzyl diselenide incorporated into the micelles is quite stable and maintains its GPx activity even after exposure to the atmosphere [23].
  • New dihydrostilbene derivatives from the leaves of Glycyrrhiza glabra and evaluation of their antioxidant activity [24].
  • In a search for novel inhibitors of RA-metabolising enzyme inhibitors as potential anti-cancer agents some 1,2-ethandiones, 2-hydroxyethanones and 1-ethylenedioxyethanones based on aryl-substituted 1,2-diphenylethane have been examined [25].
  • It was found that TNL derivatives with a shorter distance between C-4 in ring A and C'-2 in ring C were more cytotoxic, while dibenzyl-gamma-butyrolactones with a longer one were nearly inactive [26].

Analytical, diagnostic and therapeutic context of phenethylbenzene


  1. Benzothiadiazine dioxide dibenzyl derivatives as potent human cytomegalovirus inhibitors: synthesis and comparative molecular field analysis. Martinez, A., Gil, C., Abasolo, M.I., Castro, A., Bruno, A.M., Perez, C., Prieto, C., Otero, J. J. Med. Chem. (2000) [Pubmed]
  2. Anti-proliferative effects of 1,2-diphenylethane oestrogens and anti-oestrogens on human breast cancer cells. Hartmann, R.W., Sinchai, T., Kranzfelder, G. J. Cancer Res. Clin. Oncol. (1985) [Pubmed]
  3. Inhibition of diethyl ether degradation in Rhodococcus sp. strain DEE5151 by glutaraldehyde and ethyl vinyl ether. Kim, Y.H., Engesser, K.H. FEMS Microbiol. Lett. (2005) [Pubmed]
  4. In vitro anti-proliferation/cytotoxic activity of sixty natural products on the human SH-SY5Y neuroblastoma cells with specific reference to dibenzyl trisulphide. Williams, L.A., Rösner, H., Möller, W., Conrad, J., Nkurunziza, J.P., Kraus, W. The West Indian medical journal. (2004) [Pubmed]
  5. The relationship between properties of antipsychotic drugs and cataract formation. Kamei, A., Mizumoto, Y., Takehana, M. Biol. Pharm. Bull. (1994) [Pubmed]
  6. Chroman/catechol hybrids: synthesis and evaluation of their activity against oxidative stress induced cellular damage. Koufaki, M., Theodorou, E., Galaris, D., Nousis, L., Katsanou, E.S., Alexis, M.N. J. Med. Chem. (2006) [Pubmed]
  7. Investigations of new lead structures for the design of selective estrogen receptor modulators. Gust, R., Keilitz, R., Schmidt, K. J. Med. Chem. (2001) [Pubmed]
  8. Analysis of saturation transfer electron paramagnetic resonance spectra of a spin-labeled integral membrane protein, band 3, in terms of the uniaxial rotational diffusion model. Hustedt, E.J., Beth, A.H. Biophys. J. (1995) [Pubmed]
  9. Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization. Cushman, M., Nagarathnam, D., Gopal, D., Chakraborti, A.K., Lin, C.M., Hamel, E. J. Med. Chem. (1991) [Pubmed]
  10. Antimalarial polyamine analogues. Edwards, M.L., Stemerick, D.M., Bitonti, A.J., Dumont, J.A., McCann, P.P., Bey, P., Sjoerdsma, A. J. Med. Chem. (1991) [Pubmed]
  11. Dissociative protonation sites: reactive centers in protonated molecules leading to fragmentation in mass spectrometry. Tu, Y.P. J. Org. Chem. (2006) [Pubmed]
  12. A convenient synthesis of trans-3'-hydroxycotinine, a major nicotine metabolite found in the urine of tobacco users. Desai, D., Amin, S. Chem. Res. Toxicol. (1990) [Pubmed]
  13. Antineoplastic agents 389. New syntheses of the combretastatin A-4 prodrug. Pettit, G.R., Rhodes, M.R. Anticancer Drug Des. (1998) [Pubmed]
  14. Dibenzyl bromophenols with diverse dimerization patterns from the brown alga Leathesia nana. Xu, X., Song, F., Wang, S., Li, S., Xiao, F., Zhao, J., Yang, Y., Shang, S., Yang, L., Shi, J. J. Nat. Prod. (2004) [Pubmed]
  15. Synthesis and antiproliferative activity of 2,6-diamino-9-benzyl-9-deazapurine and related compounds. Otmar, M., Masojídková, M., Votruba, I., Holý, A. Bioorg. Med. Chem. (2004) [Pubmed]
  16. Central pharmacological activities and opiate receptor binding studies of some dermorphin analogs. Giagnoni, G., Parolaro, D., Crema, G., Mennuni, L., Brini, A., Casiraghi, L., Sala, M., Gori, E. Peptides (1985) [Pubmed]
  17. Synthesis and pharmacological evaluation of perhydropyrrolo [3,4-c]pyridine derivatives. Altomare, C., Carotti, A., Casini, G., Cellamare, S., Ferappi, M., Brigiani, G.S., Persichella, M. Farmaco (1990) [Pubmed]
  18. EPR investigation of persistent radicals produced from the photolysis of dibenzyl ketones adsorbed on ZSM-5 zeolites. Turro, N.J., Lei, X.G., Jockusch, S., Li, W., Liu, Z., Abrams, L., Ottaviani, M.F. J. Org. Chem. (2002) [Pubmed]
  19. Antineoplastic agents 453. Synthesis of pancratistatin prodrugs. Pettit, G.R., Orr, B., Ducki, S. Anticancer Drug Des. (2000) [Pubmed]
  20. Synthesis and antiplasmodial activity of a cysteine protease-inhibiting biotinylated aziridine-2,3-dicarboxylate. Gelhaus, C., Vicik, R., Hilgenfeld, R., Schmidt, C.L., Leippe, M., Schirmeister, T. Biol. Chem. (2004) [Pubmed]
  21. New furofuran and butyrolactone lignans with antioxidant activity from the stem bark of Styrax japonica. Min, B.S., Na, M.K., Oh, S.R., Ahn, K.S., Jeong, G.S., Li, G., Lee, S.K., Joung, H., Lee, H.K. J. Nat. Prod. (2004) [Pubmed]
  22. Synthesis of a potent antagonist of substance P by replacing the CH2SCH3 and the alpha-carboxamide groups of the methionine at [Orn6]-SP6-11 by benzyl ester groups. Karagiannis, K., Stavropoulos, G., Poulos, C., Jordan, C.C., Hagan, R.M. Int. J. Pept. Protein Res. (1993) [Pubmed]
  23. Block copolymer micelles as matrixes for incorporating diselenide compounds: a model system for a water-soluble glutathione peroxidase mimic fine-tuned by ionic strength. Wang, Y., Xu, H., Ma, N., Wang, Z., Zhang, X., Liu, J., Shen, J. Langmuir : the ACS journal of surfaces and colloids. (2006) [Pubmed]
  24. New dihydrostilbene derivatives from the leaves of Glycyrrhiza glabra and evaluation of their antioxidant activity. Biondi, D.M., Rocco, C., Ruberto, G. J. Nat. Prod. (2003) [Pubmed]
  25. Some 1,2-diphenylethane derivatives as inhibitors of retinoic acid--metabolising enzymes. Greer, V.P., Mason, P., Kirby, A.J., Smith, H.J., Nicholls, P.J., Simons, C. Journal of enzyme inhibition and medicinal chemistry. (2003) [Pubmed]
  26. 2,3-dibenzylbutyrolactones and 1,2,3,4-tetrahydro-2-naphthoic acid gamma-lactones: structure and activity relationship in cytotoxic activity. Kim, Y., You, Y.J., Nam, N.H., Ahn, B.Z. Arch. Pharm. Res. (2002) [Pubmed]
  27. Microcapsules from starch granules. Korus, J., Tomasik, P., Lii, C.Y. Journal of microencapsulation. (2003) [Pubmed]
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