73721-89-8

Upstream product

• 151-56-4 ethyleneimine 
• 98-91-9 thiobenzoic acid 
• 60-23-1 Cysteamine 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 23405-15-4 benzoic acid N-hydroxysuccinimide ester 
• 729553-08-6 C₉H₁₁NO₄S₂ 
• 156-57-0 2-mercaptoethylamine hydrochloride 
• 99071-70-2 N-(2-thiocyanato-ethyl)-benzamide 
• 27110-61-8 N-(2-Bromo-ethyl)-benzamide 
• 243990-68-3 1-(2,5-Dichlorophenyl)-2,2-bis(methylsulfanyl)vinyl benzoate 
• 17612-90-7 S-benzoylcysteamine hydrochloride 
• 5205-42-5 N,N'-(2,2'-disulfanediylbis(ethane-2,1-diyl))dibenzamide 

Downstream Products

• 99855-18-2 1-acetylsulfanyl-2-benzoylamino-ethane 
• 55065-04-8 S-2-(N-benzoylamino)ethyl benzothioathe 
• 92555-37-8 N-[2-(2,4-dinitro-phenylsulfanyl)-ethyl]-benzamide 
• 2722-34-1 2-phenylthiazoline 
• 5205-42-5 N,N'-(2,2'-disulfanediylbis(ethane-2,1-diyl))dibenzamide 
• 1137241-53-2 N-[2-(triphenylmethylsulfanyl)ethyl]benzamide 

Relevant academic research and scientific papers

Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids

Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification but is not amenable for esterification. The latter feature has been exploited to prepare hydroxyl- and thiol-containing amides.

Comparative reactivity analysis of small-molecule thiol surrogates

Targeted covalent inhibitors represent an increasingly popular approach to modulate challenging drug targets. Since covalent and non-covalent interactions are both contributing to the affinity of these compounds, evaluation of their reactivity is a key-step to find feasible warheads. There are well-established HPLC- and NMR-based kinetic assays to tackle this task, however, they use a variety of cysteine-surrogates including cysteamine, cysteine or acetyl-cysteine and GSH. The diverse nature of the thiol sources often makes the results incomparable that prevents compiling a comprehensive knowledge base for the design of covalent inhibitors. To evaluate kinetic measurements from different sources we performed a comparative analysis of the different thiol surrogates against a designed set of electrophilic fragments equipped with a range of warheads. Our study included seven different thiol models and 13 warheads resulting in a reactivity matrix analysed thoroughly. We found that the reactivity profile might be significantly different for various thiol models. Comparing the different warheads, we concluded that – in addition to its human relevance - glutathione (GSH) provided the best estimate of reactivity with highest number of true positives identified.

Reduction with tris(2-carboxyethyl)phosphine (TCEP) enables the use of an S-sulphonate protecting group for thiol-mediated bioconjugation

Herein, we demonstrate the effectiveness of the water-friendly S-sulphonate group as an alternative to traditional thiol protecting groups for subsequent deprotection-bioconjugation reactions, under conditions that are compatible with the use of biochemic

Highly Ligand Efficient and Selective N-2-(Thioethyl)picolinamide Histone Deacetylase Inhibitors Inspired by the Natural Product PsammaplinA

Novel picolinamide-based histone deacetylase (HDAC) inhibitors were developed, drawing inspiration from the natural product psammaplinA. We found that the HDAC potency and isoform selectivity provided by the oxime unit of psammaplinA could be reproduced b

CORROSION PROTECTION COATINGS

The present invention relates to new coating materials for corrosion control.

The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions

β-Hydroxy amides 6 and 7 were treated with triphenylphosphonium anhydride trifluoromethane sulfonate (3), or the cyclic analogue 4, to generate 2-oxazolines 5 and 8 under mild conditions. The reaction was optimised by examining the number of equivalents of reagents 3 or 4, or diisopropylethyl amine required to best effect cyclisation. The effects of altering the reaction temperature, reaction time, concentration, solvent, and addition rate also were investigated. However, it was found that use of a trityl group to block reaction at the hydroxyl or thiol group of the starting amides, and subsequent in situ detritylation, in the absence of base, led to greatly improved yields. Reagent 4 offered significant advantages in the purification of products and was used to dehydrate a range of trityl derivatives to form simple oxazolines, thiazolines, and a dihydro-1,3-oxazine, in high yield (85-99%), as well as a tetrahydro-1,3-oxazepine (31%).

Zeolite-catalyzed simple synthesis of different heterocyclic rings, part 2

A simple and environmentally friendly synthesis was developed for the preparation of 2-arylimidazoline derivatives and 2-arylbenzoxazole derivatives using a small pore size zeolite. The similar reaction was not applicable to the preparation of the sulfur-containing analogs cysteamine or 2-aminothiophenol, probably because of a disadvantageous reaction between the zeolite and the thio compound.

1-(2,5-dichlorophenyl)-2,2-bis(methylsulfanyl)vinyl esters as highly efficient chemoselective acylating reagents

1-(2,5-Dichlorophenyl)-2,2-bis(methylsulfanyl)vinyl esters 4f-k were prepared in yields usually greater than 90%, by reacting acyl chlorides with 1-(2,5-dichlorophenyl)-2,2-bis(methylsulfanyl)ethanone enolate. These esters were demonstrated to be excellent chemoselective reagents for the acylation of amines, alcohols, thiols, pyrrole and indole. From all the acylation reactions the dimethyl α-oxo dithioacetal 2d, recyclable for the preparation of esters 4f-k, could be recovered in 90-100% yield.