183370-70-9

Basic information

• Product Name: L-Alanine, N-(chlorophenoxyphosphinyl)-, phenylmethyl ester
• CAS NO: 183370-70-9
• Molecular Formula: C16H17ClNO4P
• Molecular Weight: 353.742
• Mol File: 183370-70-9.mol
• Article Data: 33

Chemical Properties

• CAS DataBase Reference: L-Alanine, N-(chlorophenoxyphosphinyl)-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Alanine, N-(chlorophenoxyphosphinyl)-, phenylmethyl ester(183370-70-9)
• EPA Substance Registry System: L-Alanine, N-(chlorophenoxyphosphinyl)-, phenylmethyl ester(183370-70-9)

Safety Data

• Hazardous Substances Data: 183370-70-9(Hazardous Substances Data)

Upstream product

• 108-95-2 phenol 
• 17831-01-5 H-Ala-OBzl 
• 770-12-7 O-phenyl phosphorodichloridate 
• 100-51-6 benzyl alcohol 
• 104-15-4 toluene-4-sulfonic acid 
• 42854-62-6 L-alanine benzyl ester p-toluenesulfonate 
• 5557-81-3 L-alanine benzyl ester hydrochloride 

Downstream Products

• 1202487-57-7 (2S)-benzyl 2-((((4R,6R,7S)-4-amino-2-oxopyrimidin-1(2H)-yl)-7-hydroxy-5-oxaspiro[2,4]heptan-6-yl)methoxy)((phenoxy)phosphorylamino)propanoate 
• 1170666-24-6 C₃₁H₃₃N₈O₉P 
• 840506-29-8 (2S)-benzyl 2-(((RS)-(((2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate 
• 1562406-27-2 2’-deoxy-2’,2’-difluoro-D-cytidine-5’-O-[phenyl(benzyloxy-L-alaninyl)]-(R)-phosphate 
• 1562406-27-2 benzyl ((S)-(((2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate 

Relevant articles and documents

Influence of 4′-Substitution on the Activity of Gemcitabine and Its ProTide against VZV and SARS-CoV-2

In addition to its therapeutic value as a chemotherapy drug, gemcitabine is of ongoing interest to the scientific community for its broad-spectrum antiviral activity. Herein the synthesis of 4′-methoxy- and 4′-fluoro-substituted gemcitabine analogues along with their phosphoramidate prodrugs is described. Among these derivatives, 4′-fluorogemcitabine proved to be active against varicella zoster virus (VZV, TK+ strain) with an EC50 of 0.042 μM and produced significant cytotoxicity (CC50 = 0.11 μM). Upon derivatization of this trifluoro nucleoside as its prodrug, decreased anti-VZV activity was observed, but with a concomitantly improved selectivity index (SI = 36). When this prodrug was tested against severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), its antiviral activity (EC50 = 0.73 μM) was comparable to or slightly lower than its cytotoxic concentration in measurements of cell growth and cell morphology, respectively.

2,4,7-SUBSTITUTED-7-DEAZA-2'-DEOXY-2'-FLUOROARABINOSYL NUCLEOSIDE AND NUCLEOTIDE PRO-DRUGS AND USES THEREOF

The present disclosure is concerned with 2,4,7-substituted-7-deaza-2'-deoxy-2'- fluoroarabinosyl nucleoside and nucleotide prodrugs that are capable of inhibiting viral infections and methods of treating viral infections such as, for example, human immunodeficiency virus (HIV), human papillomavirus (HPV), herpes simplex virus (HSV), human cytomegalovirus (HCMV), chicken pox, infectious mononucleosis, mumps, measles, rubella, shingles, ebola, viral gastroenteritis, viral hepatitis, viral meningitis, human metapneumovirus, human parainfluenza virus type 1, parainfluenza virus type 2, parainfluenza virus type 3, respiratory syncytial virus, viral pneumonia, Chikungunya virus (CHIKV), Venezuelan equine encephalitis (VEEV), dengue (DENV), influenza, West Nile virus (WNV), zika (ZIKV), 229E, NL63, OC43, HKU1, Middle East respiratory syndrome coronavirus (MERS-CoV), severe acute respiratory syndrome coronavirus (SARS-CoV), and severe acute respiratory syndrome coronavirus disease 2019 (SARS-CoV-2), using these compounds. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Aryloxy Triester Phosphoramidates as Phosphoserine Prodrugs: A Proof of Concept Study

The specific targeting of protein-protein interactions by phosphoserine-containing small molecules has been scarce due to the dephosphorylation of phosphoserine and its charged nature at physiological pH, which hinder its uptake into cells. To address these issues, we herein report the synthesis of phosphoserine aryloxy triester phosphoramidates as phosphoserine prodrugs that are enzymatically metabolized to release phosphoserine. This phosphoserine-masking approach was applied to a phosphoserine-containing inhibitor of 14-3-3 dimerization, and the generated prodrugs exhibited improved pharmacological activity. Collectively, this provided a proof of concept that the masking of phosphoserine with biocleavable aryloxy triester phosphoramidate masking groups is a viable intracellular delivery system for phosphoserine-containing molecules. Ultimately, this will facilitate the discovery of phosphoserine-containing small-molecule therapeutics.