The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Thiofenol     benzenethiol

Synonyms: THIOPHENOL, Phenylthiol, thiophenate, Benzenethiol, SureCN67, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of benzenethiol

  • The nature of substituent effects on cellular toxicity is examined, and they reveal that electron-releasing substituted thiophenols such as 4-amino thiophenol and the 4-alkoxy thiophenols are highly cytotoxic and effective at inhibiting cellular proliferation at physiological pH [1].
  • However, when PF was incubated with Lactobacillus brevis, an intestinal bacterium, in the presence of phenylmercaptan, the metabolizing rate of PF into 8-phenylthio-paeonimetabolin I (PT-PM-I) was found to be equivalent to that of PF into PM-I [2].

Psychiatry related information on benzenethiol

  • Reaction time for quantitative conversion of thiophenol to diphenyl disulfide was shortest for diazene UP-91, which is highly consistent with high reactivity of the same diazene with GSH, observed under quasi-physiological conditions [3].

High impact information on benzenethiol


Biological context of benzenethiol

  • The values of V/K(m) for the enzyme-catalyzed hydrolysis for a series of substituted thiophenol analogues were 10(2)-10(3)-fold smaller than those obtained for the hydrolysis of the corresponding phenolic substrates, suggesting that the bulkier sulfur substituent in the leaving group may induce conformational restrictions at the active site [9].
  • The dealkylation process occurred even after denaturation of the proteins of the membrane preparation, and it occurred in the presence of model nucleophiles imidazole and thiophenol [10].
  • Subsequent to transport into the fungal cell, enzymatic hydrolysis of these peptides resulted in the release of free thiophenol, which was quantified by using Ellman reagent [11].
  • An unprotected 16 residue peptide containing a C-terminal thioester and an N-terminal selenocysteine residue efficiently cyclizes in the presence of thiophenol; subsequent reduction, elimination or alkylation of the selenol yields modified cyclic peptides with alanine, dehydroalanine or a non-natural amino acid at the site of ligation [12].
  • Functionalized peptides and oligonucleotides were used without purification in native ligation conjugation reactions in aqueous/organic solution using tris-(2-carboxyethyl)phosphine to remove the tert-butylsulfenyl group in situ and thiophenol as a conjugation enhancer [13].

Anatomical context of benzenethiol

  • Both agents protected erythrocytes from peroxide damage by thiophenol and simultaneously enhanced its prooxidant effect in the liver [14].

Associations of benzenethiol with other chemical compounds


Gene context of benzenethiol

  • By use of visible absorption and circular dichroism spectroscopies, it is found that prior to addition of benzenethiol, modifications of the ferredoxin induced by DMF are reversible [20].
  • Induced thermolysis of tert-butyl phenylperacetates by thiophenol: simultaneous occurrence of homolysis and single electron transfer [21].
  • [reaction: see text] The radical chain reaction of benzenethiol with alkynylthiol esters provides a new, valuable protocol for the tin-free generation of acyl radicals that arise from intramolecular substitution at sulfur by the initial sulfanylvinyl radicals [22].
  • Deprotection and peptide-resin cleavage was performed with a TFA/thiophenol (H2O) mixture [23].
  • Fmoc x Ser x OAll and Fmoc x Thr x OAll bound to resin with a silyl ether linker were deallylated by Pd(0) catalysis and condensed with thiophenol, benzyl mercaptane, and ethyl 3-mercaptopropionate by activation with DCC/HOBt [24].

Analytical, diagnostic and therapeutic context of benzenethiol

  • Studies related to the relative thermodynamic stability of C-terminal peptidyl esters of O-hydroxy thiophenol: emergence of a doable strategy for non-cysteine ligation applicable to the chemical synthesis of glycopeptides [25].
  • The fit to previously published data involving benzenethiol titration of the one-electron reduced (semi-reduced) cofactor, FeMoco(sr), as followed by EPR required a model that included both a sub-stoichiometric ratio of thiol to FeMoco(sr) and about five cooperative ligand binding sites [26].
  • Scanning tunneling microscopy of sulfur and benzenethiol chemisorbed on Ru(0001) in 0.1 M HClO4 [27].
  • An HPLC assay is described that can be used to study the covalent bonding interaction of carbinolamine-containing pyrrolo[2,1-c][1,4]benzodiazepines with the model nucleophile thiophenol, in order to evaluate electrophilicity at the C-11-position [28].
  • Novel gold nanoparticles, passivated by monolayers of benzenethiol, biphenylthiol, and similar derivatives, have been synthesized and characterized using UV/vis, NMR, and Fourier transform infrared (FTIR) spectroscopies [29].


  1. Synthesis, cytotoxicity, and QSAR analysis of X-thiophenols in rapidly dividing cells. Verma, R.P., Kapur, S., Barberena, O., Shusterman, A., Hansch, C.H., Selassie, C.D. Chem. Res. Toxicol. (2003) [Pubmed]
  2. Development of a simple HPLC method for determination of paeoniflorin-metabolizing activity of intestinal bacteria in rat feces. He, J.X., Akao, T., Tani, T. Chem. Pharm. Bull. (2002) [Pubmed]
  3. Diazenecarboxamide UP-91, a potential anticancer agent, acts by reducing cellular glutathione content. Moskatelo, D., Polanc, S., Kosmrlj, J., Vuković, L., Osmak, M. Pharmacol. Toxicol. (2002) [Pubmed]
  4. Glutathione peroxidase (GPx)-like antioxidant activity of the organoselenium drug ebselen: unexpected complications with thiol exchange reactions. Sarma, B.K., Mugesh, G. J. Am. Chem. Soc. (2005) [Pubmed]
  5. Drugs that inhibit oxidation reactions catalyzed by aldehyde oxidase do not inhibit the reductive metabolism of ziprasidone to its major metabolite, S-methyldihydroziprasidone: an in vitro study. Obach, R.S., Walsky, R.L. Journal of clinical psychopharmacology. (2005) [Pubmed]
  6. Chemo- and regioselective peptide cyclization triggered by the N-terminal fatty acid chain length: the recombinant cyclase of the calcium-dependent antibiotic from Streptomyces coelicolor. Grünewald, J., Sieber, S.A., Marahiel, M.A. Biochemistry (2004) [Pubmed]
  7. Kinetics study of amine cleavage reactions of various resin-bound thiophenol esters from marshall linker. Fang, L., Demee, M., Sierra, T., Kshirsagar, T., Celebi, A.A., Yan, B. Journal of combinatorial chemistry. (2002) [Pubmed]
  8. Catalysis of the addition of benzenethiol to 2-cyclohexen-1-ones by uranyl-salophen complexes: a catalytic metallocleft with high substrate specificity. van Axel Castelli, V., Dalla Cort, A., Mandolini, L., Reinhoudt, D.N., Schiaffino, L. Chemistry (Weinheim an der Bergstrasse, Germany) (2000) [Pubmed]
  9. Metal-substrate interactions facilitate the catalytic activity of the bacterial phosphotriesterase. Hong, S.B., Raushel, F.M. Biochemistry (1996) [Pubmed]
  10. O3-(2-carbomethoxyallyl) ethers of opioid ligands derived from oxymorphone, naltrexone, etorphine, diprenorphine, norbinaltorphimine, and naltrindole. Unexpected O3-dealkylation in the opioid radioligand displacement assay. Klein, P., Nelson, W.L. J. Med. Chem. (1992) [Pubmed]
  11. Multiplicity of peptide permeases in Candida albicans: evidence from novel chromophoric peptides. McCarthy, P.J., Nisbet, L.J., Boehm, J.C., Kingsbury, W.D. J. Bacteriol. (1985) [Pubmed]
  12. Selenocysteine-mediated backbone cyclization of unprotected peptides followed by alkylation, oxidative elimination or reduction of the selenol. Quaderer, R., Hilvert, D. Chem. Commun. (Camb.) (2002) [Pubmed]
  13. Efficient conjugation of peptides to oligonucleotides by "native ligation". Stetsenko, D.A., Gait, M.J. J. Org. Chem. (2000) [Pubmed]
  14. Corrective effect of clotrimazole and beta-ionol during exposure to thiophenol. Dadali, V.A., Golovanova, N.E., Pavlova, R.N., Dzhangulova, N.E., Vinogradova, V.E. Bull. Exp. Biol. Med. (2000) [Pubmed]
  15. Mechanism-based inactivation of VanX, a D-alanyl-D-alanine dipeptidase necessary for vancomycin resistance. Aráoz, R., Anhalt, E., René, L., Badet-Denisot, M.A., Courvalin, P., Badet, B. Biochemistry (2000) [Pubmed]
  16. Thiopurine methyltransferase: structure-activity relationships for benzoic acid inhibitors and thiophenol substrates. Ames, M.M., Selassie, C.D., Woodson, L.C., Van Loon, J.A., Hansch, C., Weinshilboum, R.M. J. Med. Chem. (1986) [Pubmed]
  17. Mechanism of action of the marine natural product stypoldione: evidence for reaction with sulfhydryl groups. O'Brien, E.T., Asai, D.J., Groweiss, A., Lipshutz, B.H., Fenical, W., Jacobs, R.S., Wilson, L. J. Med. Chem. (1986) [Pubmed]
  18. Total synthesis of the ethyl ester of the major urinary metabolite of prostaglandin E(2). Taber, D.F., Teng, D. J. Org. Chem. (2002) [Pubmed]
  19. Development of capillary column packed with thiol-modified gold-coated polystyrene particles and its selectivity for aromatic compounds. Kobayashi, K., Kitagawa, S., Ohtani, H. Journal of chromatography. A. (2006) [Pubmed]
  20. Kinetics and equilibria of active site core extrusion from spinach ferredoxin in aqueous N,N-dimethylformamide/Triton X-100 solutions. Bonomi, F., Kurtz, D.M. Biochemistry (1982) [Pubmed]
  21. Induced thermolysis of tert-butyl phenylperacetates by thiophenol: simultaneous occurrence of homolysis and single electron transfer. Kim, S.S., Tuchkin, A., Kim, C.S. J. Org. Chem. (2001) [Pubmed]
  22. Generation and intramolecular reactivity of acyl radicals from alkynylthiol esters under reducing tin-free conditions. Benati, L., Calestani, G., Leardini, R., Minozzi, M., Nanni, D., Spagnolo, P., Strazzari, S. Org. Lett. (2003) [Pubmed]
  23. Chemical synthesis of O-thiophosphotyrosyl peptides. Kitas, E., Küng, E., Bannwarth, W. Int. J. Pept. Protein Res. (1994) [Pubmed]
  24. Silyl linker-based approach to the solid-phase synthesis of Fmoc glycopeptide thioesters. Ishii, A., Hojo, H., Nakahara, Y., Ito, Y., Nakahara, Y. Biosci. Biotechnol. Biochem. (2002) [Pubmed]
  25. Studies related to the relative thermodynamic stability of C-terminal peptidyl esters of O-hydroxy thiophenol: emergence of a doable strategy for non-cysteine ligation applicable to the chemical synthesis of glycopeptides. Chen, G., Warren, J.D., Chen, J., Wu, B., Wan, Q., Danishefsky, S.J. J. Am. Chem. Soc. (2006) [Pubmed]
  26. Determination of ligand binding constants for the iron-molybdenum cofactor of nitrogenase: monomers, multimers, and cooperative behavior. Frank, P., Angove, H.C., Burgess, B.K., Hodgson, K.O. J. Biol. Inorg. Chem. (2001) [Pubmed]
  27. Scanning tunneling microscopy of sulfur and benzenethiol chemisorbed on Ru(0001) in 0.1 M HClO4. Yang, L.Y., Yau, S.L., Itaya, K. Langmuir : the ACS journal of surfaces and colloids. (2004) [Pubmed]
  28. Evaluation of the electrophilicity of DNA-binding pyrrolo[2,1-c][1,4]benzodiazepines by HPLC. Morris, S.J., Thurston, D.E., Nevell, T.G. J. Antibiot. (1990) [Pubmed]
  29. Relaxation dynamics and transient behavior of small arenethiol passivated gold nanoparticles. Busby, M., Chiorboli, C., Scandola, F. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2006) [Pubmed]
WikiGenes - Universities