198062-93-0

Upstream product

• 38778-05-1 4-(Phenoxy)benzenethiol 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 831-82-3 4-Phenoxyphenol 
• 198062-96-3 O-(4-phenoxyphenyl)-N,N-dimethylthiocarbamate 

Downstream Products

• 38778-05-1 4-(Phenoxy)benzenethiol 
• 292605-13-1 3-(4-phenoxyphenylsulfonyl)propyloxirane 
• 292605-12-0 2-(4-phenoxyphenylsulfonyl)ethyloxirane 
• 292605-14-2 SB-3CT 
• 292605-11-9 2-{[(4-phenoxyphenyl)sulfonyl]methyl}oxirane 
• 292605-10-8 5-(4-phenoxyphenylsulfanyl)-1-pentene 
• 292605-09-5 4-(4-phenoxyphenylsulfanyl)-1-butene 
• 3159-49-7 3-(4-phenoxyphenylsulfanyl)-1-propene 

Relevant academic research and scientific papers

Electrochemically Catalyzed Newman-Kwart Rearrangement: Mechanism, Structure-Reactivity Relationship, and Parallels to Photoredox Catalysis

The facilitation of redox-neutral reactions by electrochemical injection of holes and electrons, also known as "electrochemical catalysis", is a little explored approach that has the potential to expand the scope of electrosynthesis immensely. To systematically improve existing protocols and to pave the way toward new developments, a better understanding of the underlying principles is crucial. In this context, we have studied the Newman-Kwart rearrangement of O-arylthiocarbamates to the corresponding S-aryl derivatives, the key step in the synthesis of thiophenols from the corresponding phenols. This transformation is a particularly useful example because the conventional method requires temperatures up to 300 °C, whereas electrochemical catalysis facilitates the reaction at room temperature. A combined experimental-quantum chemical approach revealed several reaction channels and rendered an explanation for the relationship between the structure and reactivity. Furthermore, it is shown how rapid cyclic voltammetry measurements can serve as a tool to predict the feasibility for specific substrates. The study also revealed distinct parallels to photoredox-catalyzed reactions, in which back-electron transfer and chain propagation are competing pathways.

Novel 2-arylthiopropanoyl-CoA inhibitors of α-methylacyl-CoA racemase 1A (AMACR; P504S) as potential anti-prostate cancer agents

α-Methylacyl-CoA racemase (AMACR; P504S) catalyses an essential step in the degradation of branched-chain fatty acids and the activation of ibuprofen and related drugs. AMACR has gained much attention as a drug target and biomarker, since it is found at elevated levels in prostate cancer and several other cancers. Herein, we report the synthesis of 2-(phenylthio)propanoyl-CoA derivatives which provided potent AMACR inhibitory activity (IC50 = 22–100 nM), as measured by the AMACR colorimetric activity assay. Inhibitor potency positively correlates with calculated logP, although 2-(3-benzyloxyphenylthio)propanoyl-CoA and 2-(4-(2-methylpropoxy)phenylthio)propanoyl-CoA were more potent than predicted by this parameter. Subsequently, carboxylic acid precursors were evaluated against androgen-dependent LnCaP prostate cancer cells and androgen-independent Du145 and PC3 prostate cancer cells using the MTS assay. All tested precursor acids showed inhibitory activity against LnCaP, Du145 and PC3 cells at 500 μM, but lacked activity at 100 μM. This is the first extensive structure-activity relationship study on the influence of side-chain interactions on the potency of novel rationally designed AMACR inhibitors.

An Electrocatalytic Newman-Kwart-type Rearrangement

An electrochemical approach toward rearrangement of O-aryl thiocarbamates to the corresponding S-aryl thiocarbamates is presented. The protocol requires only catalytic amounts of electric charge and allows for operation at room temperature. The electrolys

INHIBITORS OF MATRIX METALLOPROTEINASES TO TREAT NEUROLOGICAL DISORDERS

The invention provides methods to treat neurological disorders, ophthalmological disorders, or a combination thereof by administering a compound that inhibits MMPs. A compound that inhibits MMPs is represented by the compound of formula (I) shown herein.

Inhibitors of matrix metallaproteinases

The invention provides compounds that inhibit MMPs; methods for treating or preventing cancer, angiogenesis, arthritis, connective tissue disease, cardiovascular disease, inflammation or autoimmune disease in a mammal; a method for inhibiting a matrix met