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Chemical Compound Review

MOLI001243     benzonitrile

Synonyms: AC1L9P4B
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Disease relevance of MOLI001243


High impact information on MOLI001243

  • Compared to the Co complexes 9, Co4, and Co1, the first oxidation of Co3 is considerably shifted to more positive potentials, if benzonitrile instead of dichloromethane is used as solvent [6].
  • The final CS state decays obeying first-order kinetics with a lifetime of 19 micros in benzonitrile at 295 K [7].
  • In benzonitrile, on the other hand, the photoexcitation of the triad results in the fast electron transfer (< 1 ps) from photoexcited Zn(II)chlorin to fullerene [8].
  • These compounds have been synthesized by the reductive amination of 2-(3-bromophenyl)propionaldehyde with the respective amine followed by lithiation of this product and condensation with the appropriate benzonitrile [9].
  • One-electron oxidation of triarylphosphines (Ar(3)P, Ar = phenyl and substituted phenyl) in benzonitrile (PhCN) has been studied using pulse radiolysis technique [10].

Chemical compound and disease context of MOLI001243


Biological context of MOLI001243


Anatomical context of MOLI001243

  • To study mechanisms of aromatase inhibition in brain cells, a highly effective non-steroidal aromatase inhibitor (Fadrozole; 4-[5,6,7,8-tetra-hydroimidazo- (1,5-a)-pyridin-5-yl] benzonitrile HCl; CGS 16949A) was compared with endogenous C-19 steroids, known to be formed in the preoptic area, which inhibit oestrogen formation [17].
  • In order to investigate the chromosomal genotoxicity of nitrobenzene and benzonitrile, we studied the induction of micronuclei (MN) by these test compounds in V79 cells, as well as effects on the formation and stability of microtubules and on motor protein functions [18].
  • The experiments demonstrate that both nitrobenzene and benzonitrile, in millimolar concentration ranges, may lead to interference with tubulin assembly in a cell-free system [18].

Associations of MOLI001243 with other chemical compounds

  • Cells encapsulated within alginate beads (2.9 mm diameter) for protection against the current biotransformed benzonitrile to benzoic acid with a 26% reduction in the biotransformation rate, from 0.054 mmol/min/g dcw with free cells to 0.040 mmol/min/g dcw with immobilised cells [12].
  • Gas-phase complex ions containing the vanadyl (VO(2+)), vanadyl hydroxide (VOOH(+)), or vanadium(V) dioxo (VO(2)(+)) cation and nitrile (acetonitrile, propionitrile, butyronitrile, or benzonitrile) ligands were generated by electrospray ionization (ESI) for study by multiple-stage tandem mass spectrometry [19].
  • Eleven free-base corroles with different electron-donating or electron-withdrawing meso substituents were characterized as to their electrochemistry and UV-visible spectroscopy in benzonitrile (PhCN) or pyridine containing tetra-n-butylammonium perchlorate (0.1 M) [20].
  • Both, nitrobenzene and benzonitrile, induced mostly kinetochor (CREST)-positive micronuclei, thus characterising the chromosomal effects as aneugenic [18].
  • To investigate the effect of ash on the biodegradation of pesticides in soils, we measured the sorption, desorption, and biodegradation of benzonitrile in a silt loam in the presence and absence of an ash resulting from burning of wheat (Triticum aestivum L.) residue [16].

Gene context of MOLI001243

  • BACKGROUND: A phase II study of a non-steroidal selective aromatase inhibitor, YM511, 4-[N-bromobenzyl]-N-(4H-1,2,4-triazol-4-yl)amino) benzonitrile, was conducted to evaluate the anti-tumor response, dose-dependence of response rate and tolerability in postmenopausal patients with advanced breast cancer [21].
  • No histopathological changes in the olfactory mucosa or in the liver were observed following a single ip dose of any of these compounds [0.145 mmol/kg (all compounds); 0.58 mmol/kg (DFBN, DFBA and BN)] [11].
  • The nature of the effects of nitrobenzene and benzonitrile on the association of tubulin to form microtubules was confirmed by electron microscopy [18].
  • 3D-QSAR analysis has been performed on a series of previously synthesized benzonitrile derivatives, which were screened as farnesyltransferase inhibitors, using comparative molecular field analysis (CoMFA) with partial least-square fit to predict the steric and electrostatic molecular field interactions for the activity [22].
  • Resting cells cultivated on YCB-propionitrile medium showed nitrilase activity against benzonitrile [23].

Analytical, diagnostic and therapeutic context of MOLI001243


  1. Metabolism of benzonitrile and butyronitrile by Klebsiella pneumoniae. Nawaz, M.S., Heinze, T.M., Cerniglia, C.E. Appl. Environ. Microbiol. (1992) [Pubmed]
  2. Discrimination and taxonomy of geographically diverse strains of nitrile-metabolizing actinomycetes using chemometric and molecular sequencing techniques. Brandão, P.F., Clapp, J.P., Bull, A.T. Environ. Microbiol. (2002) [Pubmed]
  3. Anti-tumour effect of aromatase inhibitor, CGS16949A, on human breast cancer cells. Yano, S., Tanaka, M., Nakao, K. Eur. J. Pharmacol. (1995) [Pubmed]
  4. Studies on the mechanism of acute toxicity of nitriles in mice. Tanii, H., Hashimoto, K. Arch. Toxicol. (1984) [Pubmed]
  5. Contact urticaria syndrome from occupational benzonitrile exposure. Li, L.F., Sujan, S.A., Li, Q.X. Contact Derm. (2004) [Pubmed]
  6. Unexpected change in charge transfer behavior in a cobalt(II) porphyrin-fullerene conjugate that stabilizes radical ion pair states. Sutton, L.R., Scheloske, M., Pirner, K.S., Hirsch, A., Guldi, D.M., Gisselbrecht, J.P. J. Am. Chem. Soc. (2004) [Pubmed]
  7. Stepwise charge separation and charge recombination in ferrocene-meso,meso-linked porphyrin dimer-fullerene triad. Imahori, H., Tamaki, K., Araki, Y., Sekiguchi, Y., Ito, O., Sakata, Y., Fukuzumi, S. J. Am. Chem. Soc. (2002) [Pubmed]
  8. Time-resolved spectroscopic study on photoinduced electron-transfer processes in Zn(II)porphyrin-Zn(II)chlorin-fullerene triad. Ha, J.H., Cho, H.S., Kim, D., Lee, J.C., Kim, T.Y., Shim, Y.K. Chemphyschem : a European journal of chemical physics and physical chemistry. (2003) [Pubmed]
  9. Bulky amine analogues of ketoprofen: potent antiinflammatory agents. Schlegel, D.C., Zenitz, B.L., Fellows, C.A., Laskowski, S.C., Behn, D.C., Phillips, D.K., Botton, I., Speight, P.T. J. Med. Chem. (1984) [Pubmed]
  10. Reactivity of Triarylphosphine Peroxyl Radical Cations Generated through the Reaction of Triarylphosphine Radical Cations with Oxygen. Tojo, S., Yasui, S., Fujitsuka, M., Majima, T. J. Org. Chem. (2006) [Pubmed]
  11. Tissue-binding and toxicity of compounds structurally related to the herbicide dichlobenil in the mouse olfactory mucosa. Eriksson, C., Brandt, I., Brittebo, E. Food Chem. Toxicol. (1992) [Pubmed]
  12. The effect of whole cell immobilisation on the biotransformation of benzonitrile and the use of direct electric current for enhanced product removal. Mustacchi, R., Knowles, C.J., Li, H., Dalrymple, I., Sunderland, G., Skibar, W., Jackman, S.A. Biotechnol. Bioeng. (2005) [Pubmed]
  13. Role of wheat-residue-derived char in the biodegradation of benzonitrile in soil: nutritional stimulation versus adsorptive inhibition. Zhang, P., Sheng, G., Feng, Y., Miller, D.M. Environ. Sci. Technol. (2005) [Pubmed]
  14. Nitrile hydrolysing activities of deep-sea and terrestrial mycolate actinomycetes. Brandão, P.F., Bull, A.T. Antonie Van Leeuwenhoek (2003) [Pubmed]
  15. Detection of induced mitotic chromosome loss in Saccharomyces cerevisiae--an interlaboratory assessment of 12 chemicals. Whittaker, S.G., Zimmermann, F.K., Dicus, B., Piegorsch, W.W., Resnick, M.A., Fogel, S. Mutat. Res. (1990) [Pubmed]
  16. Reduced biodegradation of benzonitrile in soil containing wheat-residue-derived ash. Zhang, P., Sheng, G., Wolf, D.C., Feng, Y. J. Environ. Qual. (2004) [Pubmed]
  17. Action of endogenous steroid inhibitors of brain aromatase relative to fadrozole. Wozniak, A., Hutchison, J.B. J. Steroid Biochem. Mol. Biol. (1993) [Pubmed]
  18. Chromosomal genotoxicity of nitrobenzene and benzonitrile. Bonacker, D., Stoiber, T., Böhm, K.J., Unger, E., Degen, G.H., Thier, R., Bolt, H.M. Arch. Toxicol. (2004) [Pubmed]
  19. Generation of Gas-Phase VO(2+), VOOH(+), and VO(2)(+)-Nitrile Complex Ions by Electrospray Ionization and Collision-Induced Dissociation. Parsons, Z., Leavitt, C., Duong, T., Groenewold, G.S., Gresham, G.L., Van Stipdonk, M.J. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  20. Electrochemistry and spectroelectrochemistry of meso-substituted free-base corroles in nonaqueous media: reactions of (Cor)H3, [(Cor)H4]+, and [(Cor)H2]-. Shen, J., Shao, J., Ou, Z., E, W., Koszarna, B., Gryko, D.T., Kadish, K.M. Inorganic chemistry. (2006) [Pubmed]
  21. Early phase II study of the new aromatase inhibitor YM511 in postmenopausal patients with breast cancer. Difficulty in clinical dose recommendation based on preclinical and phase I findings. Tominaga, T., Suzuki, T. Anticancer Res. (2003) [Pubmed]
  22. 3D-QSAR studies of farnesyltransferase inhibitors: a comparative molecular field analysis approach. Puntambekar, D., Giridhar, R., Yadav, M.R. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
  23. Metabolism of benzonitrile by Cryptococcus sp. UFMG-Y28. Rezende, R.P., Dias, J.C., Ferraz, V., Linardi, V.R. J. Basic Microbiol. (2000) [Pubmed]
  24. Periodic trends in electrode-chemisorbate bonding: benzonitrile on platinum-group and other noble metals as probed by surface-enhanced Raman spectroscopy combined with density functional theory. Mrozek, M.F., Wasileski, S.A., Weaver, M.J. J. Am. Chem. Soc. (2001) [Pubmed]
  25. Enhanced biotransformations and product recovery in a membrane bioreactor through application of a direct electric current. Mustacchi, R., Knowles, C.J., Li, H., Dalrymple, I., Sunderland, G., Skibar, W., Jackman, S.A. Biotechnol. Bioeng. (2005) [Pubmed]
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