42718-18-3

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-amino-2-(4-fluorophenyl)acetate hydrochloride is used as a precursor in the synthesis of various pharmaceuticals for its potential role in the treatment of neurological disorders and psychiatric conditions. Its unique structural properties make it a valuable component in the development of new drugs.
Used in Drug Development:
In the field of drug development, Methyl 2-amino-2-(4-fluorophenyl)acetate hydrochloride is employed as a key intermediate in the creation of novel therapeutic agents. Its functional groups and reactivity contribute to the design and synthesis of compounds with potential therapeutic benefits.
It is crucial to handle and dispose of Methyl 2-amino-2-(4-fluorophenyl)acetate hydrochloride with care due to its potential risks to human health and the environment if mismanaged.

Upstream product

• 67-56-1 methanol 
• 93939-74-3 (R)-2-(4-fluorophenyl)glycine 
• 7292-73-1 (2RS)-N-(p-fluorophenyl)glycine 
• 19883-57-9 (S)-2-amino-2-(4-fluorophenyl)acetic acid 
• 185994-15-4 (S)-α-amino-α-(4-fluorophenyl)acetic acid hydrochloride 

Downstream Products

• 730964-78-0 methyl 2-isocyano-2-(4-fluorophenyl)acetate 
• 1012886-64-4 methyl 2-(4-fluorophenyl)-2-formamidoacetate 
• 1456506-65-2 (S)-methyl 2-((4-((tert-butoxycarbonyl)amino)cyclohexyl)amino)-2-(4-fluorophenyl)acetate 
• 1587732-42-0 (S)-2-amino-2-(4-fluorophenyl)acetohydrazide 
• 888028-36-2 (1S)-1-amino-1-(4-fluorophenyl)-2-methylpropan-2-ol 
• 174770-74-2 (R)-2-amino-2-(4-fluorophenyl)ethanol 
• 19883-57-9 (S)-2-amino-2-(4-fluorophenyl)acetic acid 

Relevant academic research and scientific papers

Cobalt-Catalyzed, Directed C-H Functionalization/Annulation of Phenylglycinol Derivatives with Alkynes

A new method for cobalt-catalyzed C(sp2)-H functionalization of phenylglycinol derivatives with terminal and internal alkynes directed by picolinamide auxiliary has been developed. This method offers an efficient and highly regioselective route for the synthesis of 1-hydroxymethyltetrahydroisoquinolines. The reaction employs commercially available Co(II) catalyst in the presence of Mn(III) cooxidant and oxygen as a terminal oxidant and proceeds with full preservation of original stereochemistry.

NiH-Catalyzed Remote Asymmetric Hydroalkylation of Alkenes with Racemic α-Bromo Amides

Reported here is a terminal-selective, remote asymmetric hydroalkylation of olefins with racemic α-bromo amides. The reaction proceeds by NiH-catalyzed alkene isomerization and subsequent alkylation reaction, and can enantioconvergently introduce an unsymmetrical secondary alkyl group from a racemic α-bromo amide onto a terminal C(sp3)?H position along the hydrocarbon chain of the alkene. This mild process affords a range of structurally diverse chiral α-alkylalkanoic amides in excellent yields, and high regio- and enantioselectivities. In addition, the synthetic utility of this protocol is further highlighted by the regioconvergent conversion of industrial raw materials of isomeric olefin mixtures into enantioriched α-alkylalkanoic amides on large scale.

((S)-3-Mercapto-2-methylpropanamido)acetic acid derivatives as metallo-β-lactamase inhibitors: Synthesis, kinetic and crystallographic studies

The emergence and global spread of metallo-β-lactamase (MBL) mediated resistance to almost all β-lactam antibacterials poses a serious threat to public health. Since no clinically useful MBL inhibitors have been reported, there is an urgent need to develop new potent broad-spectrum MBL inhibitors effective against antibacterial resistance. Herein, we synthesized a set of 2-substituted ((S)-3-mercapto-2-methylpropanamido) acetic acid derivatives, some of which displayed potent inhibition with high ligand efficiency to the clinically relevant MBL subtypes, Verona Integron-encoded MBL (VIM)-2 and New Delhi MBL (NDM)-1. Kinetic studies revealed that the inhibitors are not strong zinc chelators in solution, and they bind reversibly to VIM-2 but dissociate very slowly. Crystallographic analyses revealed that they inhibit VIM-2 via chelating the active site zinc ions and interacting with catalytically important residues. Further cell- and zebrafish-based assays revealed that the inhibitors slightly increase susceptibility of E. coli cells expressing VIM-2 to meropenem, and they have no apparent toxicity to the viability of HEK293T cells and the zebrafish embryogenesis.

Structure-based design of inhibitors of the aspartic protease endothiapepsin by exploiting dynamic combinatorial chemistry

Structure-based design (SBD) can be used for the design and/or optimization of new inhibitors for a biological target. Whereas de novo SBD is rarely used, most reports on SBD are dealing with the optimization of an initial hit. Dynamic combinatorial chemistry (DCC) has emerged as a powerful strategy to identify bioactive ligands given that it enables the target to direct the synthesis of its strongest binder. We have designed a library of potential inhibitors (acylhydrazones) generated from five aldehydes and five hydrazides and used DCC to identify the best binder(s). After addition of the aspartic protease endothiapepsin, we characterized the protein-bound library member(s) by saturation-transfer difference NMR spectroscopy. Cocrystallization experiments validated the predicted binding mode of the two most potent inhibitors, thus demonstrating that the combination of de novo SBD and DCC constitutes an efficient starting point for hit identification and optimization. The dynamic duo: The combination of de novo structure-based design and dynamic combinatorial chemistry has been applied to the identification of novel acylhydrazone-based inhibitors for the aspartic protease endothiapepsin. 1H-STD-NMR spectroscopy has been used to identify the binders from the dynamic combinatorial libraries. Proposed binding modes of the most potent inhibitors have been confirmed by X-ray crystallography.

SUBSTITUTED PIPERAZINO-DIHYDROTHIENOPYRIMIDINES

The invention relates to new piperidino-dihydrothienopyrimidines of formula 1, as well as pharmacologically acceptable salts thereof, wherein X is SO or SO2, but preferably SO, and wherein R1, R2, R3 and R4 may have the meanings given in claim 1, as well as pharmaceutical compositions which contain these compounds. These new piperidino-dihydrothienopyrimidines are suitable for the treatment of respiratory or gastrointestinal complaints or diseases, inflammatory diseases of the joints, skin or eyes, diseases of the peripheral or central nervous system or cancers.

Dihydrothienopyrimidines for the Treatment of Inflammatory Diseases

The invention relates to new dihydrothienopyrimidine of formula 1, as well as pharmacologically acceptable salts, diastereomers, enantiomers, racemates, hydrates or solvates thereof, wherein X is SO or SO2, but preferably SO, and wherein R1, R2 and R3 have the meanings given in the description, and which are suitable for the treatment of respiratory or gastrointestinal complaints or diseases, inflammatory diseases of the joints, skin or eyes, diseases of the peripheral or central nervous system or cancers, as well as pharmaceutical compositions which contain these compounds.