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

• The factors that are responsible for the relatively low glutathione peroxidase (GPx)-like antioxidant activity of organoselenium compounds such as ebselen (1, 2-phenyl-1,2-benzisoselenazol-3(2H)-one) in the reduction of hydroperoxides with aromatic thiols such as benzenethiol and 4-methylbenzenethiol as cosubstrates are described [4].
• Aldehyde oxidase catalyzes the first reaction, a reduction of the benzisothiazole ring to dihydroziprasidone, and thiol methyltransferase catalyzes the second reaction, methylation of the thiophenol group to yield S-methyldihydroziprasidone [5].
• The best rates for cyclization were determined for the thiophenol substrate, revealing that chemical reactivity is more important than cofactor recognition [6].
• The kinetics of cleavage reactions of seven resin-bound thiophenol esters with three amines has been studied by single-bead FTIR [7].
• Catalysis of the addition of benzenethiol to 2-cyclohexen-1-ones by uranyl-salophen complexes: a catalytic metallocleft with high substrate specificity [8].

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

• Inactivation was associated with the elimination of fluoride ion as deduced from (19)F NMR spectroscopy analysis and with the production of fluorinated thiophenol dimer 12 [15].
• These results suggest that benzoic acid inhibitors of and thiophenol substrates for TPMT may interact with different sites on the enzyme [16].
• We examined the ability of stypoldione to add to sulfhydryl groups of a number of thiol-containing substances, including glutathione, thiophenol, beta-mercaptoethanol, and the protein tubulin [17].
• The key step is the kinetic opening of the TBS-protected bicyclic ketone 7 with thiophenol [18].
• Three types of thiol compounds (n-octadecanethiol, thiophenol, and 2-phenylethanethiol) were used to modify the gold-coated polystyrene particles (dp. 5microm) to prepare a stationary phase for capillary liquid chromatography through the formation of self-assembled monolayer [19].

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].

References