69489-40-3

Usage

Uses

Used in Pharmaceutical Industry:
D-2-[p-(benzyloxy)phenyl]glycine is used as a synthetic intermediate for the production of various pharmaceuticals. Its unique structure allows it to be incorporated into the synthesis of a wide range of drug molecules, contributing to the development of new therapeutic agents.
Used in Agrochemical Industry:
D-2-[p-(benzyloxy)phenyl]glycine is also used as a synthetic intermediate in the production of agrochemicals. Its potential applications in this field include the development of new pesticides, herbicides, and other agricultural chemicals that can improve crop yields and protect plants from pests and diseases.
Used in Medicinal Chemistry Research:
Due to its potential biological activity, D-2-[p-(benzyloxy)phenyl]glycine is a subject of interest in medicinal chemistry research. Scientists are investigating its properties and exploring its potential applications in the development of new drugs and therapies for various diseases and conditions.

Upstream product

• 22818-40-2 D-4-hydroxyphenylglycine 
• 100-39-0 benzyl bromide 

Downstream Products

• 127526-64-1 (R)-(4-benzyloxyphenyl)(tert-butoxycarbonylamino)acetic acid 
• 124620-58-2 D-N-(triphenylmethyl)-4-(benzyloxy)phenylglycine 
• 123004-72-8 D-glycine tert-butyl ester toluenesulfonate salt 
• 103300-70-5 N-<(o-nitrophenyl)sulfenyl>-D-p-(benzyloxy)phenylglycine 
• 71336-83-9 Methyl-D-p-benzyloxyphenylglycinat 
• 312328-61-3 (R)-Alloc-Hpg(OBn)-OH 
• 323192-76-3 (2S,4R)-2-phenyl-4-((4-phenylmethoxy)phenyl)-5-oxo-3-oxazolidinecarboxylic acid methyl ester 
• 677009-86-8 (3R,1'R)-3-methyl-2-[2-hydroxy-1-(4-benzyloxyphenyl)ethyl]-2,3-dihydro-1H-isoindolin-1-one 
• 677009-93-7 (R)-N-[2-hydroxy-1-(4-benzyloxyphenyl)ethyl]phthalimide 
• 677009-94-8 2-[(R)-1-(4-Benzyloxy-phenyl)-2-hydroxy-ethyl]-3-hydroxy-3-methyl-2,3-dihydro-isoindol-1-one 
• 677009-88-0 (3R,1'R)-3-n-propyl-2-[2-hydroxy-1-(4-benzyloxyphenyl)ethyl]-2,3-dihydro-1H-isoindolin-1-one 
• 677009-95-9 2-[(R)-1-(4-Benzyloxy-phenyl)-2-hydroxy-ethyl]-3-ethyl-3-hydroxy-2,3-dihydro-isoindol-1-one 
• 677009-96-0 2-[(R)-1-(4-Benzyloxy-phenyl)-2-hydroxy-ethyl]-3-hydroxy-3-propyl-2,3-dihydro-isoindol-1-one 
• 677009-98-2 2-[(R)-1-(4-Benzyloxy-phenyl)-2-hydroxy-ethyl]-3-hydroxy-3-isobutyl-2,3-dihydro-isoindol-1-one 

Relevant academic research and scientific papers

A NEW CLASS OF FLAVIVIRUS PROTEASE INHIBITORS

The present invention relates to compounds that inhibit the activity of flavivirus.

Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture

The viral serine protease NS2B-NS3 is one of the promising targets for drug discovery against dengue virus and other flaviviruses. The molecular recognition preferences of the protease favor basic, positively charged moieties as substrates and inhibitors, which leads to pharmacokinetic liabilities and off-target interactions with host proteases such as thrombin. We here present the results of efforts that were aimed specifically at the discovery and development of noncharged, small-molecular inhibitors of the flaviviral proteases. A key factor in the discovery of these compounds was a cellular reporter gene assay for the dengue protease, the DENV2proHeLa system. Extensive structure-activity relationship explorations resulted in novel benzamide derivatives with submicromolar activities in viral replication assays (EC50 0.24 μM), selectivity against off-target proteases, and negligible cytotoxicity. This structural class has increased drug-likeness compared to most of the previously published active-site-directed flaviviral protease inhibitors and includes promising candidates for further preclinical development.

A New Class of Dengue and West Nile Virus Protease Inhibitors with Submicromolar Activity in Reporter Gene DENV-2 Protease and Viral Replication Assays

Dengue and West Nile virus are rapidly spreading global pathogens for which no specific therapeutic treatments are available. One of the promising targets for drug discovery against dengue and other flaviviruses is the viral serine protease NS2B-NS3. We present the design, synthesis, and in vitro and cellular characterization of a novel chemotype of potent small-molecule non-peptidic dengue protease inhibitors derived from 4-benzyloxyphenylglycine. A newly developed luciferase-based DENV-2 protease reporter system in HeLa cells (DENV2proHeLa) was employed to determine the activity of the compounds in a cellular environment. Specificity and selectivity of the DENV2proHeLa system were confirmed by viral titer reduction assays. The compounds reach low micromolar to upper nanomolar inhibitory potency in cell-based assays, are selective against other serine proteases, and do not show relevant cytotoxicity. An extensive structure-activity relationship study provides a perspective for further drug development against flaviviral infections.

Discovery of Nanomolar Dengue and West Nile Virus Protease Inhibitors Containing a 4-Benzyloxyphenylglycine Residue

The dengue virus (DENV) and West Nile Virus (WNV) NS2B-NS3 proteases are attractive targets for the development of dual-acting therapeutics against these arboviral pathogens. We present the synthesis and extensive biological evaluation of inhibitors that

Syntheses of amino alcohols and chiral C2-symmetric bisoxazolines derived from O-alkylated R-4-hydroxyphenylglycine and S-tyrosine

Chiral C2-symmetric bisoxazolines 1b-f and 2b,c, derived from 4′-O-alkylated R-4-hydroxyphenylglycine or S-tyrosine, were prepared. As intermediates, a series of chiral amino alcohols possessing substituted phenolic groups was prepared and fully characterized.

Solid-phase synthesis using (Allyloxy)carbonyl(Alloc) chemistry of a putative heptapeptide intermediate in vancomycin biosynthesis containing m-chloro-3-hydroxytyrosine

A convenient method for the solid-phase synthesis of putative linear heptapeptide intermediates in vancomycin biosynthesis is described, in particular, the heptapeptide D-Leu-Cyt-L-Asn-Hpg-Hpg-Cyt'-Dhpg (Cyt = (2R,3R)-m-chloro-3-hydroxytyrosine, Hpg = (R)-2-(p-hydroxyphenyl)glycine, Cyt' = (2S,3R)-m-chloro-3-hydroxytyrosine and Dhpg = (S)-2-(3,5-dihydroxyphenyl)glycine). The synthesis was performed on chlorotrityl resin and employed the (allyloxy)carbonyl protecting group for temporary N(α) protection during peptide-chain assembly.

Stereoselective synthesis of (S)-MPPG, (S)-MTPG and (S)-(+)-αM4CPG from (R)-4-hydroxyphenylglycine

(R)-4-Hydroxyphenylgrycine was protected with a benzyl group and a methyl group was introduced at the α position by using the self-regeneration-of-stereocentre method. After the 4-hydroxy group had been converted into the corresponding trifluoromethanesulfonate (triflate), three palladium-catalyzed reactions were employed to furnish (S)-α-methyl-4-phosphonophenylglycine [(S)-MPPG], (S)-α-methyl-4-(tetrazol-5-yl)phenylglycine [(S)-MTPG] and (S)-4-carboxyphenyl-α-methylglycine [(S)-αM4CPG], a class of new and selective antagonists of metabotropic glutamate receptors.

Stereoselective synthesis of (S)-(+)-αM4CPG, a selective antagonist of metabotropic glutamate receptors

The synthesis, from (R)-4-hydroxyphenylglycine, of (+)-α-methyl-4- carboxy-phenylglycine ((+)-αM4CPG), a new and selective antagonist of metabotropic glutamate receptor, and assignment of its absolute configuration, are described.