18681-52-2

Usage

InChI:InChI=1/CH3BrS/c1-3-2/h1H3

Upstream product

• 75-18-3 dimethylsulfide 
• 7175-75-9 methylthio radical 
• 624-92-0 Dimethyldisulphide 

Downstream Products

• 38771-86-7 3-Bromo-3-methyl-2-methylsulfanyl-N-phenyl-butyramide 
• 84224-66-8 methyl sulfenyl triflate 
• 1147711-13-4 4-methylphenyl 3-methylsulfurylprop-2-yn-1-yl ether 
• 1073343-63-1 C₁₃H₁₉BrN₂OS₂ 
• 1073-29-6 2-(methylsulfenyl)phenol 

Relevant academic research and scientific papers

Synthetic antitumor vaccines containing MUC1 glycopeptides with two immunodominant domains-induction of a strong immune response against breast tumor tissues

A shot in the arm for cancer treatment: Two MUC1 tetanus toxoid vaccines were synthesized and induced a strong immune response in mice. The antibodies elicited by the vaccines show a high selectivity for the tumor cells in mammary carcinoma tissues and al

FT-IR kinetic and product study of the bmnitiated oxidation of dimethyl sulfide

An FT-IR kinetic and product study of the Br-atom-initiated oxidation of dimethyl sulh'de (DMS) has been performed in a large-volume reaction chamber at 298 K and 1000mbar total pressure as a function of the bath gas composition (N2 + O2). In the kinetic investigations using the relative kinetic method, considerable scatter was observed between individual determinations of the rate coefficient, suggesting the possibility of interference from secondary chemistry in the reaction system involving dimethyl sulfoxide (DMSO) formation. Despite the experimental difficulties, an overall bimolecular rate coefficient for the reaction of Br atoms with DMS under atmospheric conditions at 298 K of 1 × 10-13 cm3 molecule-' s-1 can be deduced. The major sulfur products observed included SO2, CH3SBr, and DMSO. The kinetic observations in combination with the product studies under the conditions employed are consistent with rapid addition of Br atoms to DMS forming an adduct that mainly re-forms reactants but can also decompose unimolecularly to form CH3SBr and CH3 radicals. The observed formation of DMSO is attributed to reactions of BrO radicals with DMS rather than reaction of the Br-DMS adduct with O2 as has been previously speculated and is thought to be responsible for the variability of the measured rate coefficient. The reaction CH3O2 + Br → BrO + CH2O is postulated as the source of BrO radicals.

Synthesis and immunological evaluation of MUC1 glycopeptide conjugates bearing: N -acetyl modified STn derivatives as anticancer vaccines

Glycoprotein MUC1 is an attractive target for anti-tumor vaccine development. However, the weak immunogenicity of MUC1 remains a significant problem. To solve this problem, several STn derivatives with N-acetyl modifications were synthesized and incorporated into a 20-amino acid MUC1 tandem repeat sequence. The modified STn-MUC1 glycopeptides were further connected to a carrier protein keyhole limpet hemocyanin (KLH). The immunological effects of these synthetic vaccine conjugates were evaluated using the BALB/c mouse model. The results showed that vaccine V2 elicited higher titers of antibodies which cross-reacted with the native STn-MUC1 antigen. Moreover, the elicited antisera reacted with the STn-MUC1 antigen-positive tumor cells, indicating that the carbohydrate antigen modification strategy may hold potential to overcome the weak immunogenicity of natural MUC1 glycopeptides.

Opening of thiiranes: Preparation of orthogonal protected 2-thioglyceraldehyde

Treatment of acrolein diethyl acetal sulfide 8 with methanesulfenyl bromide at low temperature results in an efficient thiirane ring opening to a halo disulfide 9. The bromine in this halo disulfide is easily substituted by silver acetate, sodium azide, sodium iodide, and silver nitrate. Treatment of 9 with tetrabutylammonium acetate yields a novel dehydrohalogenation product 12. Silica gel converts bromide 9 into a disulfide-substituted version of acrolein 15. The orthogonal-protected version of 2-thioglyceraldehyde 13 can be deprotected to a useful form of this aldehyde.

Design, synthesis and biological evaluation of sulfenimine cephalosporin sulfoxides as β-lactamase inhibitors

Abstract A series of sulfenimine cephalosporin sulfoxide derivatives (7a-v) were designed, synthesized and evaluated for their inhibitory activity against TEM-1 and cephalosporinase in cell-free systems. Some of the tested compounds showed enhanced inhibi

Regioselective deacetylation and glycosylation in the synthesis of the sialyl lewis0 X tetrasaccharide, a key component of the recognition site of PSGL-1

A high-yielding regioselective deprotection of three out of five hydroxy groups of a Lewis X trisaccharide, which proceeds under very mild basic conditions, and a regio- and stereoselective sialylation reaction enable an efficient access to the sialyl Lew

Fluorinated glycosyl amino acids for mucin-like glycopeptide antigen analogues

The aberrant glycosylation profiles of mucin glycoproteins on epithelial tumour cells represent attractive target structures for the development of immunotherapy against cancer. Mucin-type glycopeptides have been successfully investigated as molecularly defined vaccine prototypes for triggering humoral immunity but are susceptible to rapid in vivo degradation. As a potential means to enhance the bioavailabilities of the antigenic structures, hydrolysis-resistant carbohydrate analogues with fluorine substituents at positions C6, C2′ and C6′ were synthesised and incorporated into the tandem repeat sequence of the mucin MUC1. The resulting pseudo-glycopeptides can be used to elucidate the effects of chemically modified antibody determinants on metabolic and immunological properties.

Preparation of N,N-Dimethyl-N′-arylureas using S,S-dimethyl dithio-carbonate as a carbonylating reagent

A new, general method for the preparation of N,N-di-methyl-N′- arylureas using S,S-dimethyl dithiocarbonate as a phosgene substitute is reported. The method has been set up according to four procedures, all including three steps: (1) reaction of S,S-di- methyl dithiocarbonate with dimethylamine to give S-methyl N,N-dimethylthiocarbamate; (2) halogenation with various halogenating reagents (chlorine, methanesulfenyl chloride, bromine, and meth-anesulfenyl bromide) to give N,N-dimethylcarbamoyl chloride or bromide; (3) in situ reaction with primary arylamines. All the target products were obtained in high yields (85-98%; 16 reactions, average yield 93%) and with high purity. Also noteworthy is the recovery of byproducts of industrial interest, namely methanethiol and dimethyl disulfide, with complete exploitation of the reagent S,S- dimethyl dithiocarbonate. Georg Thieme Verlag Stuttgart.

Ganglioside GM3 derivatives with truncated ceramide moiety: Facial synthesis and inhibitory activity against KB cell growth

An expeditious sialylation reaction with phenylthioglycoside 4 as a sialyl donor and MeSOTf as a promoter was developed. These conditions are very useful for synthesizing ganglioside GM 3 (1), its C8-ceramide analog 2, and 3-deoxy analog 3 of 2 in an efficient manner. The GM 3 analog 2, whose hydrophilicity is increased by shortening the ceramide moiety, exhibits increased growth inhibiton of KB cells. The 3-hydoxy group of ceramide does not influence its activity against KB cells. Copyright Taylor & Francis Group, LLC.

Biomimetic synthesis of the tumor-associated (2,3)-sialyl-T antigen and its incorporation into glycopeptide antigens from the mucins MUC1 and MUC4

Glycoproteins on epithelial tumor cells often exhibit aberrant glycosylation profiles. The incomplete formation of the glycan side chains resulting from a down-regulated glucosamine transfer and a premature sialylation results in additional peptide epitop