166318-79-2

Basic information

• Product Name: 1-Hydroxy-1-(3-nitrophenyl)methylphosphonate 5',5'-di-O-(3'-azido-2',3'-dideoxythymidinyl) ester
• Synonyms: 1-Hydroxy-1-(3-nitrophenyl)methylphosphonate 5',5'-di-O-(3'-azido-2',3'-dideoxythymidinyl) ester
• CAS NO: 166318-79-2
• Molecular Weight: 731.575
• Mol File: 166318-79-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-Hydroxy-1-(3-nitrophenyl)methylphosphonate 5',5'-di-O-(3'-azido-2',3'-dideoxythymidinyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxy-1-(3-nitrophenyl)methylphosphonate 5',5'-di-O-(3'-azido-2',3'-dideoxythymidinyl) ester(166318-79-2)
• EPA Substance Registry System: 1-Hydroxy-1-(3-nitrophenyl)methylphosphonate 5',5'-di-O-(3'-azido-2',3'-dideoxythymidinyl) ester(166318-79-2)

Safety Data

• Hazardous Substances Data: 166318-79-2(Hazardous Substances Data)

Upstream product

• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 99-61-6 3-nitro-benzaldehyde 
• 151029-28-6 5',5'-Di-O-(3'-azido-2',3'-dideoxythymidinyl) H-phosphonate diester 

Downstream Products

• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 124930-59-2 3'-azido-3'-deoxythymidin-5'-yl H-phosphonate monoester 
• 173606-90-1 5',5'-Di-O-(3'-azido-2',3'-dideoxythymidinyl)-O'-(3-nitrobenzyl) phosphotriester 

Relevant articles and documents

Lipophilic &α-Hydroxybenzylphosphonates as Prodrugs of 3'-Azido-2',3'-dideoxythymidine (AZT)

The α-hydroxybenzylphosphonates 1a-1j of the antiviral drug 3'-azido-2',3'-dideoxythymidine 5 (AZT) as potential lipophilic prodrugs were readily accessible in 49percent to 87percent yield via a four-step synthetic pathway introducing the modifications in the aromatic ring system in the last step by making use of intermediate 6.All compounds 1a-1j exhibited higher partition coefficients in 1-octanol/water than AZT (5).In hydrolysis studies at pH 7.5 we observed that precursors to bioactive compounds were delivered by simple hydrolysis of the lipophilic precursors 1a-1j via two different mechanisms: the phosphonate-phosphate rearrangement leading to the benzylphosphotriesters 2 and/or the direct cleavage into the di-AZT phosphonate 6.Both compounds 2 and 6 were further degraded yielding the potentially antiviral active compounds 4 and 8, respectively.The hydrolysis pathway could be controlled by the substitution pattern in the benzylic moiety.Identical hydrolytic behavior of 1 was detected in "biological" hydrolysis kinetics by using a RPMI culture medium containing 10percent heat-inactivated fetal calf serum (FCS).The title compounds 1a-1j exhibited considerable HIV-1 and HIV-2 activity in wild-type CEM/O cells. - Keywords: AZT; Nucleoside α-hydroxybenzylphosphonates; Phosphonate-phosphate rearrangement; Prodrugs; HIV chemotherapy