24312-63-8

Upstream product

• 1121-24-0 ortho-mercaptophenol 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 95-55-6 2-amino-phenol 
• 150-60-7 dibenzyl disulphide 
• 108-94-1 cyclohexanone 
• 95-56-7 2-hydroxybromobenzene 

Downstream Products

• 86787-96-4 2,2-Dimethyl-propionic acid 2-benzylsulfanyl-phenyl ester 
• 86787-98-6 Benzoic acid 2-benzylsulfanyl-phenyl ester 
• 1425927-72-5 (2-benzylsulfanyl-phenoxy)-acetic acid methyl ester 
• 1425927-07-6 (2-{[(3-methyl-2-oxo-1,2-dihydroquinolin-6-yl)amino]sulfonyl}phenoxy)acetic acid 
• 1425927-06-5 2-(2-hydroxy-2-methylpropoxy)-N-(3-methyl-2-oxo-1,2-dihydroquinolin-6-yl)benzenesulfonamide 
• 1425927-73-6 (2-chlorosulfonyl-phenoxy)-acetic acid methyl ester 
• 1425927-05-4 methyl (2-{[(3-methyl-2-oxo-1,2-dihydroquinolin-6-yl)amino]sulfonyl}phenoxy)acetate 
• 86788-00-3 1-(2-Hydroxy-phenylsulfanyl)-3,3-dimethyl-1-phenyl-butan-2-one 
• 86788-02-5 α-(2-hydroxy-phenylsulfanyl)-deoxybenzoin 
• 29634-37-5 2-(benzylsulfonyl)phenol 
• 29634-49-9 2-(benzylsulfinyl)phenol 

Relevant academic research and scientific papers

Structure Property Relationships of Carboxylic Acid Isosteres

The replacement of a carboxylic acid with a surrogate structure, or (bio)-isostere, is a classical strategy in medicinal chemistry. The general underlying principle is that by maintaining the features of the carboxylic acid critical for biological activity, but appropriately modifying the physicochemical properties, improved analogs may result. In this context, a systematic assessment of the physicochemical properties of carboxylic acid isosteres would be desirable to enable more informed decisions of potential replacements to be used for analog design. Herein we report the structure-property relationships (SPR) of 35 phenylpropionic acid derivatives, in which the carboxylic acid moiety is replaced with a series of known isosteres. The data set generated provides an assessment of the relative impact on the physicochemical properties that these replacements may have compared to the carboxylic acid analog. As such, this study presents a framework for how to rationally apply isosteric replacements of the carboxylic acid functional group.

Enantioselective syntheses of sulfoxides in octahedral ruthenium(II) complexes via a chiral-at-metal strategy

The preparation of chiral 2-(alkylsulfinyl)phenol compounds by enantioselective coordination-oxidation of the thioether ruthenium complexes with a chiral-at-metal strategy has been developed. The enantiomerically pure sulfoxide complexes δ-[Ru(bpy)2{(R)-LO-R}](PF6) (bpy is 2,2′-bipyridine, HLO-R is 2-(alkylsulfinyl)phenol, R = Me (δ-1a), Et (δ-2a), iPr (δ-3a), Bn (δ-4a), and Nap (δ-5a)) and δ-[Ru(bpy)2{(S)-LO-R}](PF6) (R = Me (δ-1a), Et (δ-2a), iPr (δ-3a), Bn (δ-4a), and Nap (δ-5a)) have been synthesized by the reaction of δ-[Ru(bpy)2(py)2]2+ or δ-[Ru(bpy)2(py)2]2+ with the prochiral thioether ligands 2-(alkylthio)phenol (HL-R), followed by enantioselective oxidation with m-CPBA as oxidant. The X-ray crystallography was used to verify the stereochemistry of ruthenium complexes and sulfur atoms. The configurations of the ruthenium complexes are stable during the coordination and oxidation reactions. Moreover, the chiral sulfoxide ligands are enantioselectively generated by controlling of the configuration of ruthenium centers in the course of oxidation reaction. That is, the δ configuration at the ruthenium center generates the S sulfoxide ligand; on the contrary, the δ configuration of the ruthenium complex originates the R sulfoxide ligand. Acidolysis of δ-[Ru(bpy)2{(R)-LO-R}](PF6) and δ-[Ru(bpy)2{(S)-LO-R}](PF6) complexes in the presence of TFA-MeCN afforded the chiral ligands (R)-HLO-R and (S)-HLO-R in 96-99% ee values, respectively. Importantly, the chiral ruthenium complexes can be recycled as δ/δ-[Ru(bpy)2(MeCN)2](PF6)2 and reused in a next reaction cycle with complete retention of the configurations at ruthenium centers.

A highly efficient Cu-catalyzed S-transfer reaction: From amine to sulfide

A highly efficient Cu-catalyzed dual C-S bonds formation reaction, proceeding in alcohol and water under air, is reported, in which inodorous stable Na2S2O3 is used as a sulfurating reagent. This powerful strategy provides a practical and efficient approach to construct thioethers, using readily available aromatic amines and alkyl halides as starting materials. Sensitive and synthetic useful functional groups could be tolerated. Furthermore, pharmaceuticals, glucose, an amino acid, and a chiral ligand are successfully furnished by this late-stage sulfuration strategy.

Design and chemoproteomic functional characterization of a chemical probe targeted to bromodomains of BET family proteins

Bromodomain-containing proteins form the signal-reading element of a principal system for the control of gene expression in eukaryotes. Their potential as targets for selective drug action is increasingly being assessed and exploited. Deep characterizatio

NOVEL HETEROCYCLIC COMPOUNDS AS BROMODOMAIN INHIBITORS

Disclosed are compounds of Formula (I): (I) which are useful as bromodomain inhibitors. Pharmaceutical compositions containing compounds of Formula (I) and the use of compounds of Formula (I) to treat diseases or disorders that are bromodomain-dependent are also disclosed. Methods for preparing and using these compounds are further described.

Iodine-catalyzed selective synthesis of 2-sulfanylphenols via oxidative aromatization of cyclohexanones and disulfides

Iodine-catalyzed intermolecular dehydrogenative aromatizations of six-membered cyclohexanones for the selective synthesis of 2-sulfanylphenols have been developed. Both aryl and alkyl disulfides can be used as sulfanylation reagents to give the desired pr

A simple one-pot synthesis of hydroxylated and carboxylated aryl alkyl sulfides from various bromobenzenes

A simple one-pot synthesis of aryl alkyl sulfides from various bromobenzenes containing a hydroxy, hydroxymethyl, hydroxyethyl, and carboxylic acid group at -o, -m, and -p positions is reported here. The reaction proceeds through, in sequence, in situ pro

Covalent modification of cyclooxygenase-2 (COX-2) by 2-acetoxyphenyl alkyl sulfides, a new class of selective COX-2 inactivators

All of the selective COX-2 inhibitors described to date inhibit the isoform by binding tightly but noncovalently at the substrate binding site. Recently, we reported the first account of selective covalent modification of COX-2 by a novel inactivator, 2-acetoxyphenyl hept-2-ynyl sulfide (70) (Science 1998, 280, 1268-1270). Compound 70 selectively inactivates COX-2 by acetylating the same serine residue that aspirin acetylates. This paper describes the extensive structure-activity relationship (SAR) studies on the initial lead compound 2-acetoxyphenyl methyl sulfide (36) that led to the discovery of 70. Extension of the S-alkyl chain in 36 with higher alkyl homologues led to significant increases in inhibitory potency. The heptyl chain in 2-acetoxyphenyl heptyl sulfide (46) was optimum for COX-2 inhibitory potency, and introduction of a triple bond in the heptyl chain (compound 70) led to further increments in potency and selectivity. The alkynyl analogues were more potent and selective COX-2 inhibitors than the corresponding alkyl homologues. Sulfides were more potent and selective COX-2 inhibitors than the corresponding sulfoxides or sulfones or other heteroatom-containing compounds. In addition to inhibiting purified COX-2, 36, 46, and 70 also inhibited COX-2 activity in murine macrophages. Analogue 36 which displayed moderate potency and selectivity against purified human COX-2 was a potent inhibitor of COX-2 activity in the mouse macrophages. Tryptic digestion and peptide mapping of COX-2 reacted with [1-14C-acetyl]-36 indicated that selective COX-2 inhibition by 36 also resulted in the acetylation of Ser516. That COX-2 inhibition by aspirin resulted from the acetylation of Ser516 was confirmed by tryptic digestion and peptide mapping of COX-2 labeled with [1- 14C-acetyl]salicyclic acid. The efficacy of the sulfides in inhibiting COX- 2 activity in inflammatory cells, our recent results on the selectivity of 70 in attenuating growth of COX-2-expressing colon cancer cells, and its selectivity for inhibition of COX-2 over COX-1 in vivo indicate that this novel class of covalent modifiers may serve as potential therapeutic agents in inflammatory and proliferative disorders.

Medium-ring Ketone Synthesis. Intramolecular Acylation of Sulfur-stabilized Carbanions: A Model Study

Intramolecular acylation of the sulfur-stabilized carbanions of the acyclic ester 9 and amide sulfides 11 was carried out as a model study for developing an effective method for the construction of medium-ring ketones by ring closure.Reaction of 9a-c or 11a-g with lithium diisopropylamide (LDA) proceeded smoothly and the expected keto sulfides 10a-c or 12a-g, respectively, were obtained.In the cases where R1 and/or R2 in 11 were normal alkyl groups, the reaction did not take place.However, these difficulties were readily overcome either by introducing a methyl group next to the carbonyl group or by converting the sulfides into the corresponding sulfoxides or sulfones.Acylation in the allyl sulfides 11b, d, f and the allyl sulfone 20b takes place at the α-position to the sulfur atom, yielding β,γ-unsaturated ketones.A reductive removal of the sulfide moiety or its conversion into other functional groups was also examined.