220592-64-3

Basic information

• Product Name: phenyl (pentoxy-L-alaninyl)-phosphorochloridate
• Synonyms: phenyl (pentoxy-L-alaninyl)-phosphorochloridate
• CAS NO: 220592-64-3
• Molecular Weight: 333.752
• Mol File: 220592-64-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: phenyl (pentoxy-L-alaninyl)-phosphorochloridate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl (pentoxy-L-alaninyl)-phosphorochloridate(220592-64-3)
• EPA Substance Registry System: phenyl (pentoxy-L-alaninyl)-phosphorochloridate(220592-64-3)

Safety Data

• Hazardous Substances Data: 220592-64-3(Hazardous Substances Data)

Upstream product

• 770-12-7 O-phenyl phosphorodichloridate 

Relevant articles and documents

Application of ProTide technology to gemcitabine: A successful approach to overcome the key cancer resistance mechanisms leads to a new agent (NUC-1031) in clinical development

Gemcitabine is a nucleoside analogue commonly used in cancer therapy but with limited efficacy due to a high susceptibility to cancer cell resistance. The addition of a phosphoramidate motif to the gemcitabine can protect it against many of the key cancer resistance mechanisms. We have synthesized a series of gemcitabine phosphoramidate prodrugs and screened for cytostatic activity in a range of different tumor cell lines. Among the synthesized compounds, one in particular (NUC-1031, 6f) was shown to be potent in vitro. Importantly, compared with gemcitabine, 6f activation was significantly less dependent on deoxycytidine kinase and on nucleoside transporters, and it was resistant to cytidine deaminase-mediated degradation. Moreover, 6f showed a significant reduction in tumor volumes in vivo in pancreatic cancer xenografts. The ProTide 6f is now in clinical development with encouraging efficacy signals in a Phase I/II study, which strongly supports the ProTide approach to generate promising new anticancer agents.