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Chemical Compound Review

Tosylamide     4-methylbenzenesulfonamide

Synonyms: p-Tosylamide, CHEMBL574, SureCN7370, AGN-PC-009IBX, NSC-9908, ...
 
 
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Disease relevance of P-TOLUENESULFONAMIDE

 

High impact information on P-TOLUENESULFONAMIDE

  • With norbornene and p-toluenesulfonamide as the substrates and 1 as the catalyst, intermediate [(COD)Pt(norbornene)2][OTf]2 (3) was identified and characterized by 19F and 195Pt NMR spectroscopies and mass spectrometry [5].
  • The key transformations include the generation of an alkylidenecarbene intermediate through intramolecular addition of a tosylamide anion to an alkynyliodonium salt, and the cycloaddition of that carbene to a peri positioned aromatic ring to afford a cycloheptatrienylidene product featuring the intact pareitropone skeleton [6].
  • Cyclization of an alcohol containing pendant monosubstituted and trisubstituted olefins catalyzed by either triflic acid or metal triflates form products from addition to the more substituted olefin, and additions of tosylamide catalyzed by triflic acid or metal triflates form indistinguishable ratios of the two N-alkyl sulfonamides [7].
  • The kinetics and mechanisms of chlorine transfer from chloramine-T (CAT) to several amines are second order and independent of p-toluenesulfonamide concentration; thus, the reaction does not involve disproportionation of CAT to dichloramine-T [8].
  • The influence of the binding of the high-affinity inhibitor, 4-methylbenzenesulfonamide, to the active site of bovine carbonic anhydrase B was studied by 15N- and 13C-NMR spectroscopy [9].
 

Biological context of P-TOLUENESULFONAMIDE

 

Associations of P-TOLUENESULFONAMIDE with other chemical compounds

 

Analytical, diagnostic and therapeutic context of P-TOLUENESULFONAMIDE

References

  1. Increased mutagenicity of some nitroimidazoles by non-mutagenic nitrotoluene on Klebsiella pneumoniae (fluctuation test). Voogd, C.E., van der Stel, J.J., van Bruchem, M.C. Mutat. Res. (1992) [Pubmed]
  2. Desquamative gingivitis, sole manifestation of tosylamide/formaldehyde resin allergy. Staines, K.S., Felix, D.H., Forsyth, A. Contact Derm. (1998) [Pubmed]
  3. Mutagenicity study of Remsen-Fahlberg saccharin and contaminants. Eckhardt, K., King, M.T., Gocke, E., Wild, D. Toxicol. Lett. (1980) [Pubmed]
  4. The aetiology of eyelid dermatitis: a 10-year retrospective analysis. Amin, K.A., Belsito, D.V. Contact Derm. (2006) [Pubmed]
  5. Platinum-based catalysts for the hydroamination of olefins with sulfonamides and weakly basic anilines. Karshtedt, D., Bell, A.T., Tilley, T.D. J. Am. Chem. Soc. (2005) [Pubmed]
  6. Alkynyliodonium salts in organic synthesis. Application to the total synthesis of the tropoloisoquinoline alkaloid pareitropone. Feldman, K.S., Cutarelli, T.D. J. Am. Chem. Soc. (2002) [Pubmed]
  7. Hydroamination and hydroalkoxylation catalyzed by triflic Acid. Parallels to reactions initiated with metal triflates. Rosenfeld, D.C., Shekhar, S., Takemiya, A., Utsunomiya, M., Hartwig, J.F. Org. Lett. (2006) [Pubmed]
  8. Kinetics and mechanism of chlorine exchange between chloramine-T and secondary amines. Dannan, H., Crooks, P.A., Dittert, L.W., Hussain, A. Journal of pharmaceutical sciences. (1992) [Pubmed]
  9. 13C and 15N NMR and time-resolved fluorescence depolarization study of bovine carbonic anhydrase--4-methylbenzenesulfonamide complex. Jarvet, J., Olivson, A., Mets, U., Pooga, M., Aguraiuja, R., Lippmaa, E. Eur. J. Biochem. (1989) [Pubmed]
  10. Determination of chloramine T in dairy products. van Gils, W.F., Visser, G., Hidskes, G.G. Zeitschrift für Lebensmittel-Untersuchung und -Forschung. (1975) [Pubmed]
  11. Comparative metabolism of tolbutamide by isolated hepatocytes from rat, rabbit, dog, and squirrel monkey. Gee, S.J., Green, C.E., Tyson, C.A. Drug Metab. Dispos. (1984) [Pubmed]
  12. Determination of p-toluenesulfonamide in ice cream by combination of continuous flow and liquid chromatography: summary of collaborative study. Beljaars, P.R., van Dijk, R., Brands, A. Journal of AOAC International. (1994) [Pubmed]
  13. Development and validation of a gas chromatography/mass spectrometry procedure for confirmation of para-toluenesulfonamide in edible fish fillet tissue. Idowu, O.R., Kijak, P.J., Meinertz, J.R., Schmidt, L.J. Journal of AOAC International. (2004) [Pubmed]
  14. Interaction of cobalt-bovine carbonic anhydrase with the acetate ion. Bertini, I., Luchinat, C., Scozzafava, A. Biochim. Biophys. Acta (1976) [Pubmed]
 
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