70200-11-2

Upstream product

• 105-36-2 ethyl bromoacetate 
• 446-52-6 2-Fluorobenzaldehyde 
• 1071-46-1 hydrogen ethyl malonate 
• 141-78-6 ethyl acetate 

Downstream Products

• 91319-58-3 3-acetoxy-3-(2-fluorophenyl)propanol 
• 91319-57-2 3-benzyloxy-1-(2-fluorophenyl)propanol 
• 91319-59-4 1-acetoxy-1-(2-fluorophenyl)-3-benzyloxypropane 
• 60187-07-7 3-hydroxy-3-(2-fluorophenyl)propanoic acid 
• 91319-56-1 3-hydroxy-3-(2'-fluorophenyl)propanol 

Relevant academic research and scientific papers

Evaluation of a new protocol for enzymatic dynamic kinetic resolution of 3-hydroxy-3-(aryl)propanoic acids

The application of tandem metal-enzyme dynamic kinetic resolution (DKR) is a powerful tool for the manufacture of high-value chemical commodities. A new protocol of kinetic resolution based on irreversible enzymatic esterification of carboxylic acids with orthoesters was introduced to obtain optically active β-hydroxy esters. This procedure was combined with metal catalyzed racemization of the target substrate providing both (R) and (S) enantiomers of ethyl 3-hydroxy-3-(4-nitrophenyl)propanoate with a high yield of 89% at 40°C. A substantial influence of the enzyme type, organic co-solvent, and metal catalyst on the conversion and enantioselectivity of the enzymatic dynamic kinetic resolution was noted.

Synthesis, molecular docking and kinetic properties of β-hydroxy- β-phenylpropionyl-hydroxamic acids as Helicobacter pylori urease inhibitors

Inhibition of urease results in Helicobacter pylori growth arrest in the stomach, promoting urease as promising targets for gastrointestinal ulcer therapy. Twenty hybrid derivatives of flavonoid scaffold and hydroxamic acid, β-hydroxy-β-phenylpropionylhydroxamic acids, were therefore synthesized and evaluated against H. pylori urease. Biological evaluation of these compounds showed improved urease inhibition exhibiting micromolar to mid-nanomolar IC50 values. Most importantly, 3-(3-chlorophenyl)-3- hydroxypropionyl-hydroxamic acid (6g) exhibited high potency with IC 50 of 0.083 ± 0.004 μM and Ki of 0.014 ± 0.003 μM, indicating that 6g is an excellent candidate to develop novel antiulcer agent. A mixture of competitive and uncompetitive mechanism was putatively proposed to understand the inconsistency between the crystallographic and kinetic studies for the first time, which is supported by our molecular docking studies.

Environmentally benign metal-free decarboxylative aldol and Mannich reactions

Aiming at the development of green and efficient C-C bond formations (aldol and Mannich reactions), the decarboxylative nucleophilic addition of malonic acid half ester to imines or aldehydes under mild metal-free conditions was studied. A careful control of the temperature and the appropriate choice of the organic base allowed us to obtain β-amino esters or β-hydroxy esters including α-substituted and α,α-disubstituted ones in moderate to excellent yields. 1H NMR monitoring of the reaction unveiled two distinct mechanisms depending on the hemimalonate used. With the unsubstituted substrate, a carboxylic acid intermediate was isolated upon acid quench resulting from the nucleophilic addition of the putative enol carboxylate anion of the hemimalonate to imines/aldehydes before CO2 loss. With substituted hemimalonates, the reaction likely involved an enolate which then added to imines/aldehydes or was competitively protonated. According to the base used, the reaction can be carried out either under solvent free-conditions or in an ionic liquid under mild conditions.

Pradefovir: A prodrug that targets adefovir to the liver for the treatment of hepatitis B

Adefovir dipivoxil, a marketed drug for the treatment of hepatitis B, is dosed at submaximally efficacious doses because of renal toxicity. In an effort to improve the therapeutic index of adefovir, 1-aryl-1,3-propanyl prodrugs were synthesized with the r