142629-80-9

Basic information

• Product Name: L-Alanine, N-(chlorophenoxyphosphinyl)-, methyl ester
• CAS NO: 142629-80-9
• Molecular Formula: C10H13ClNO4P
• Molecular Weight: 277.644
• Mol File: 142629-80-9.mol
• Article Data: 45

Chemical Properties

• CAS DataBase Reference: L-Alanine, N-(chlorophenoxyphosphinyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Alanine, N-(chlorophenoxyphosphinyl)-, methyl ester(142629-80-9)
• EPA Substance Registry System: L-Alanine, N-(chlorophenoxyphosphinyl)-, methyl ester(142629-80-9)

Safety Data

• Hazardous Substances Data: 142629-80-9(Hazardous Substances Data)

Upstream product

• 108-95-2 phenol 
• 770-12-7 O-phenyl phosphorodichloridate 
• 67436-20-8 p-toluenesulfonic acid salt of (S)-α-alanine 
• 10065-72-2 L-Alanine methyl ester 
• 2491-20-5 L-alanine methyl ester hydrochloride 

Downstream Products

• 1206473-95-1 C₂₇H₂₆ClN₂O₇P 
• 1206473-98-4 C₂₈H₂₉N₂O₇P 
• 1206473-94-0 C₂₇H₂₇N₂O₇P 

Relevant articles and documents

Kinase-independent phosphoramidate S1P1receptor agonist benzyl ether derivatives

Previously published S1P receptor modulator benzyl ether derivatives have shown potential as being viable therapeutics for the treatment of neurodegenerative diseases, however, two of the most S1P1-selective compounds are reported as being poorly phosphorylated by kinases in vivo. Phosphoramidates of BED compounds (2a, 2b) were synthesised with the aim of producing kinase-independent S1P receptor modulators. Carboxypeptidase, human serum and cell lysate processing experiments were conducted. ProTide BED analogues were found to have an acceptable level of stability in acidic and basic conditions and in vitro metabolic processing experiments showed that they are processed to the desired pharmacologically active monophosphate. The research describes the development of an entirely novel family of therapeutic agents.

Synthesis of a phosphoramidate pro-drug of 6-thio-7-deaza-2′-deoxyguanosine (TDG): A regioselective phosphorylation

6-Thio-7-deaza-2′-deoxyguanosine-5′-triphosphate (TDG-TP) is a potent inhibitor of human telomerase. Regioselective synthesis of the 5′-phenyl methoxyalaninyl phosphate pro-drug of 6-thio-7-deaza-2′-deoxyguanosine (TDG) has been achieved in good yields by the reaction of TDG with phenyl methoxyalaninyl phosphochloridate in the presence of N-methylimidazole at -70°C. This pro-drug of TDG is effective in producing measurable levels of TDG-TP in A549 cells.

Design, synthesis, and anti-HIV activity of 2′,3′-didehydro-2′,3′-dideoxyuridine (d4U), 2′,3′-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives

We report the synthesis of 2′,3′-didehydro-2′,3′-dideoxyuridine (d4U) and 2′,3′-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives and their evaluation against HIV-1 and HIV-2. In addition, we conducted molecular modeling studies on both d4U and ddU monophosphates to investigate their second phosphorylation process. The findings from the modeling studies provide compelling evidence for the lack of anti-HIV activity of d4U phosphoramidates, in contrast with the corresponding ddU phosphoramidates.

2′-Fluoro-6′-methylene-carbocyclic adenosine phosphoramidate (FMCAP) prodrug: In vitro anti-HBV activity against the lamivudine-entecavir resistant triple mutant and its mechanism of action

Novel 2′-fluoro-6′-methylene-carbocyclic adenosine (FMCA) monophosphate prodrug (FMCAP) was synthesized and evaluated for its in vitro anti-HBV potency against a lamivudine-entecavir resistant clone (L180M + M204V + S202G). FMCA demonstrated significant antiviral activity against wild-type as well as lamivudine-entecavir resistant triple mutant (L180M + M204V + S202G). The monophosphate prodrug (FMCAP) demonstrated greater than 12-fold (12×) increase in anti-HBV activity without increased cellular toxicity. Mitochondrial and cellular toxicity studies of FMCA indicated that there is no significant toxicity up to 100 μM. Mode of action studies by molecular modeling indicate that the 2′-fluoro moiety by hydrogen bond as well as the Van der Waals interaction of the carbocyclic ring with the phenylalanine moiety of the polymerase promote the positive binding, even in the drug-resistant mutants.

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.

PRODRUGS OF A CDK INHIBITOR FOR TREATING CANCERS

There are provided compounds of Formula I, and pharmaceutically acceptable salts and esters thereof, and pharmaceutical compositions thereof, used for inhibition or modulation of the activity of cyclin dependent kinases (CDK) and/or glycogen synthase kinase-3 (GSK-3), for the treatment of disease states or conditions mediated by cyclin dependent kinases and/or glycogen synthase kinase-3, including cancers. (I)