6493-73-8

Usage

Uses

Used in Pharmaceutical Industry:
BENZYL TRISULFIDE is used as an antibacterial and antifungal agent for its ability to combat bacterial and fungal infections. Its effectiveness in this application is attributed to its chemical properties, which allow it to disrupt the cell membranes of pathogens and inhibit their growth.
Used in Medical Research:
BENZYL TRISULFIDE is used as a research compound for studying erythrocyte elasticity, relaxation time, and membrane morphology. Its impact on these parameters can provide valuable insights into the underlying mechanisms of various blood-related disorders and contribute to the development of novel therapeutic strategies.

InChI:InChI=1/C14H14S3/c1-3-7-13(8-4-1)11-15-17-16-12-14-9-5-2-6-10-14/h1-10H,11-12H2

Upstream product

• 100-53-8 phenylmethanethiol 
• 100-39-0 benzyl bromide 
• 150-60-7 dibenzyl disulphide 
• 2949-92-0 methanethiosulfonic acid S-methyl ester 
• 103-49-1 dibenzylamine 
• 1939-99-7 benzenesulfonyl chloride 
• 23670-27-1 Sodium; phenyl-methanethiosulfonate 
• 6313-36-6 benzyl thiosulphate 
• 859323-48-1 acetyl-benzyl-trisulfane 
• 34813-71-3 benzyl-trisulfane 
• 5797-02-4 acetyl benzyl disulfide 
• 3492-66-8 benzyl-disulfane 
• 33704-38-0 2-(benzylsulfinothioyl)isoindoline-1,3-dione 
• 16192-35-1 diimidazolylsulfide 

Downstream Products

• 27657-11-0 1-benzyl-2-propyldisulfane 
• 75030-40-9 benzyl n-propyl trisulfide 
• 150-60-7 dibenzyl disulphide 
• 103-19-5 di(p-tolyl) disulfide 
• 16601-17-5 phenyl phenylmethyl disulfide 
• 16599-23-8 Benzyl 4-methylphenyl trisulfane 
• 4816-54-0 dibenzyl tetrasulfide 
• 3878-45-3 triphenylphosphine sulfide 
• 791-28-6 Triphenylphosphine oxide 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 7783-06-4 hydrogen sulfide 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

3,4-Dichloro-1,2,5-thiadiazole: a commercially available electrophilic sulfur transfer agent and safe resource of ethanedinitrile

3,4-Dichloro-1,2,5-thiadiazole is introduced as a safe and efficient sulfur transfer reagent. By applying this commercially available reagent, the symmetrical trisulfides and ethanedinitrile were simultaneously obtained by reacting various thiols with this reagent at room temperature. This reagent is non-toxic, inexpensive, and commercially available. In addition, no higher-order polysulfides were detected in all cases after the completion of the reaction. The short reaction times (20–50 min), excellent selectivity, and high yield of the trisulfides are some attractive merits of this reagent for the preparation of trisulfides. The reaction is one-pot, and isolation-purification of intermediates is not required. The procedure was readily scaled up to 5 grams. A mechanism is presented to explain the chemistry.

Selectivity of diallyl trisulfides (DATS) in reducing HAuCl4 to produce gold nanoparticles: a detailed investigation

The bulbous root garlic (Allium sativum) with a strong taste and pungent odor is used widely in culinary preparations and folk medicine. Silver and gold nanoparticles (NPs) synthesized using this ingredient have also shown medicinal and therapeutic potency. Garlic contains organosulfur compounds, such as diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DATS). These compounds are of crucial significance as anticancer drugs. Reported here is a synthesis of a series of DATS with varying substituents and plausible application as capping as well as reducing agent to synthesize gold nanoparticles (TS-GNPs). In the process, it was discovered that among the selected DATs, only 1,3-di(but-1-ene)trisulfane could serve the purpose because of structural reasons. The reason for this intriguing selectivity has been investigated in detail using the experimental findings and theoretical calculations of the frontier molecular orbitals (FMO). Graphic abstract: Synthesis of a series of medicinally important symmetrical organic trisulfides as a structural analogue of diallyl trisulfides (DATS) in an attempt to construct organosulfur compound induced gold nanoparticles (GNPs), has been reported. Only 1,3-Di(but-1-ene)trisulfane in the lot is capable of reducing the chloroauric acid to synthesize the protected GNPs.[Figure not available: see fulltext.].

Effects of sulfane sulfur content in benzyl polysulfides on thiol-triggered H2S release and cell proliferation

Investigations into hydrogen sulfide (H2S) signaling pathways have demonstrated both the generation and importance of persulfides, which are reactive sulfur species that contain both reduced and oxidized sulfur. These observations have led researchers to suggest that oxidized sulfur species, including sulfane sulfur (S0), are responsible for many of the physiological phenomena initially attributed to H2S. A common method of introducing S0 to biological systems is the administration of organic polysulfides, such as diallyl trisulfide (DATS). However, prior reports have demonstrated that commercially-available DATS often contains a mixture of polysulfides, and furthermore a lack of structure-activity relationships for organic polysulfides has limited our overall understanding of different polysulfides and their function in biological systems. Advancing our interests in the chemical biology of reactive sulfur species including H2S and S0, we report here our investigations into the rates and quantities of H2S release from a series of synthetic, pure benzyl polysulfides, ranging from monosulfide to tetrasulfide. We demonstrate that H2S is only released from the trisulfide and tetrasulfide, and that this release requires thiol-mediated reduction in the presence of cysteine or reduced glutathione. Additionally, we demonstrate the different effects of trisulfides and tetrasulfides on cell proliferation in murine epithelial bEnd.3 cells.

Trisulfides over disulfides: Highly selective synthetic strategies, anti-proliferative activities and sustained H2S release profiles

Temperature-and solvent-induced selective synthesis of trisulfides and disulfides is demonstrated. A remarkable selectivity was achieved using Na2S as a sulfur-Transfer agent under mild, greener, catalyst-free and additive-free conditions. This study reveals trisulfides as a better model than disulfides in general for a sustained release of H2S and potent anti-cancer activities.

An Esterase-Sensitive Prodrug Approach for Controllable Delivery of Persulfide Species

A strategy to deliver a well-defined persulfide species in a biological medium is described. Under near physiological conditions, the persulfide prodrug can be activated by an esterase to generate a “hydroxymethyl persulfide” intermediate, which rapidly collapses to form a defined persulfide. Such persulfide prodrugs can be used either as chemical tools to study persulfide chemistry and biology or for future development as H2S-based therapeutic reagents. Using the persulfide prodrugs developed in this study, the reactivity between S-methyl methanethiosulfonate (MMTS) with persulfide was unambiguously demonstrated. Furthermore, a representative prodrug exhibited potent cardioprotective effects in a murine model of myocardial ischemia-reperfusion (MI/R) injury with a bell shape therapeutic profile.

Microwave-assisted synthesis of thioamides with elemental sulfur

Thioamides are prepared in moderate-to-good yields from the benzylamines or benzylamine derivatives by treatment with elemental sulfur under microwave and solvent-free conditions at 170.C in 15 min.

Synthesis, stability, and reactivity of [(TPA)Zn(SH)]+ in aqueous and organic solutions

Reaction of the complex [(TPA)Zn(H2O)]2+ [TPA = tris(2-pyridylmethyl)amine] with hydrogen sulfide in aqueous buffered solution gives the corresponding monomeric hydrogensulfido complex [(TPA)Zn(SH)] +, which was fully characterized, including by XRD. This complex is stable at neutral pH, but decomposes under basic conditions to yield the free ligand and zinc sulfide, and under acidic conditions to give hydrogen sulfide and the starting aqua complex. In organic solvents, the coordinated sulfur atom reacts with electrophiles such as methylmethanethiosulfonate to yield methyltrisulfide. Reaction with the hydroxo complex [(TpPh,Me)Zn(OH)] [TpPh,Me = hydridotris{(5-methyl-3-phenyl)pyrazolyl}borate] promotes the formation of the unsymmetrical dinuclear μ-sulfido species [(TPA)Zn-S-Zn(TpPh,Me)]+, which, upon treatment with one molar equivalent of trifluoroacetic acid, dissociates into [(Tp Ph,Me)Zn(SH)] and [(TPA)Zn(CF3CO2)] +, resulting in the transfer of the hydrogensulfido ligand from one zinc center to another.

Copper(I)/S8 reversible reactions leading to an end-on bound dicopper(II) disulfide complex: Nucleophilic reactivity and analogies to copper-dioxygen chemistry

Elemental sulfur (S8) reacts reversibly with the copper(I) complex [(TMPA′)CuI]+ (1), where TMPA′ is a TMPA (tris(2-pyridylmethyl)amine) analogue with a 6-CH2OCH 3 substituent on one pyridyl ligand arm, affording a spectroscopically pure end-on bound disulfido-dicopper(II) complex [{(TMPA′)CuII}2(μ-1,2-S2 2-)]2+ (2) {ν(S-S) = 492 cm-1; ν(Cu-S)sym = 309 cm-1}; by contrast, [(TMPA)Cu I(CH3CN)]+ (3)/S8 chemistry produces an equilibrium mixture of at least three complexes. The reaction of excess PPh3 with 2 leads to formal "release" of zerovalent sulfur and reduction of copper ion to give the corresponding complex [(TMPA′)-CuI(PPh3)]+ (11) along with S=PPh3 as products. Dioxygen displaces the disulfur moiety from 2 to produce the end-on Cu2O2 complex, [{(TMPA′)Cu II}2(μ-1,2-O22-)]2+ (9). Addition of the tetradentate ligand TMPA to 2 generates the apparently more thermodynamically stable [{(TMPA)CuII}2(μ-1,2-S 22-)]2+ (4) and expected mixture of other species. Bubbling 2 with CO leads to the formation of the carbonyl adduct [(TMPA′)CuI-(CO)]+ (8). Carbonylation/sulfur- release/CO-removal cycles can be repeated several times. Sulfur atom transfer from 2 also occurs in a near quantitative manner when it is treated with 2,6-dimethylphenyl isocyanide (ArNC), leading to the corresponding isothiocyanate (ArNCS) and [(TMPA′)CuI(CNAr)]+ (12). Complex 2 readily reacts with PhCH2Br: [{(TMPA′)Cu II}2(μ-1,2-S22-)]2+ (2) + 2 PhCH2Br → [{(TMPA′)-CuII(Br)} 2]2+ (6) + PhCH2SSCH2Ph. The unprecedented substrate reactivity studies reveal that end-on bound μ-1,2-disulfide-dicopper(II) complex 2 provides a nucleophilic S 22- moiety, in striking contrast to the electrophilic behavior of a recently described side-on bound μ-η2: η2-disulfido-dicopper(II) complex, [{(N3)Cu II}2(μ-η2:η2-S 22-)]2+ (5) with tridentate N3 ligand. The investigation thus reveals striking analogies of copper/sulfur and copper/dioxygen chemistries, with regard to structure type formation and specific substrate reactivity patterns.

Synthesis and anti-tumor evaluation of new trisulfide derivatives

New bis-aromatic and heterocyclic trisulfide derivatives 5, 7-10 were synthesized by optimizing lead dibenzyl trisulfide natural product (4) to evaluate their anti-tumor activities. Five compounds 5-7, 9, and 10 exhibited potent anti-tumor activities against eight different tumor cell lines with low cytotoxicity against HepG2. Initial SAR was discussed, and MOA of these anti-microtubule agents was suggested based on cell kinetic response patterns observed on RT-CES system.

Substituted organosulfur compounds and methods of using thereof

The present invention provides substituted di-, tri-, tetra- and penta-sulfide compounds and compositions, and methods of using the same for the treatment and/or prevention of a cell proliferative disorder. The present invention also provides methods for preparing trisulfide compounds and compositions.