82857-71-4

Upstream product

• 82870-68-6 5-benzyl-2,4-dichloro-pyrimidine 
• 124-41-4 sodium methylate 

Downstream Products

• 114894-53-0 5-benzyl-2'-deoxy-2'-phthalimidoethoxymethyl-2-oxo-4-methoxypyrimidine 
• 1041365-54-1 5-benzyl-4-methoxypyrimidin-2(1H)-one 
• 119835-71-1 R-(+)-5-benzyl-1-<(1'-aminomethyl-2'-hydroxyethoxy)methyl>uracil hydrochloride 
• 130999-46-1 S-(-)-5-benzyl-1-<(1'-aminomethyl-2'-hydroxyethoxy)methyl>uracil hydrochloride 
• 119835-82-4 R-(+)-5-benzyl-1-<(1'-phtalimidomethyl-2'-benzyloxyethoxy)methyl>uracil 
• 119835-92-6 S-(-)-5-benzyl-1-<(1'-phtalimidomethyl-2'-benzyloxyethoxy)methyl>uracil 
• 119835-77-7 S-(-)-5-benzyl-1-<(1'-phtalimidomethyl-2'-benzyloxyethoxy)methyl>-2-oxo-4-methoxypyrimidine 
• 119835-81-3 R-(+)-5-benzyl-1-<(1'-phtalimidomethyl-2'-benzyloxyethoxy)methyl>-2-oxo-4-methoxypyrimidine 
• 114894-50-7 5-benzyl-1-<(1'-phthalimidomethyl-2'-benzyloxyethoxy)methyl>-2-oxo-4-methoxypyrimidine 

Relevant academic research and scientific papers

Pyrimidine acyclic nucleotide analogues with aromatic substituents in C-5 position

NH2-protected 5-phenylcytoslne and its derivatives 2a-2d were treated with (2S)-2-[(trityloxy)methyl]oxirane (3) followed by etheriflcation with diisopropyl [(tosyloxy)methyl]phosphonate (5) in the presence of sodium hydride. The intermediary phosphonate esters 6 were debenzoylated and subsequently transformed to free phosphonic acids, i.e. (S)-1-[3-hydroxy-2- (phosphonomethoxy)propyl]-5-phenylcytosine (5-phenyl-HPMPC) derivatives (8a-8d) by the action of bromotrimethylsilane and subsequent hydrolysis. Deamination of these compounds with 3-methylbutyl nitrite afforded corresponding (S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-phenyluracil (5-phenyl-HPMPU) derivatives (9a-9d). R-Enantiomers 14 and 15 were prepared analogously starting from (2R)-2-[(trityloxy)methyl]oxirane. 5-Benzyl-, 5-[(1-naphthyl)methyl]- and 5-[(2-naphthyl)methyl]HPMPU (24a-24c) and -HPMPC (25a-25c) were synthesized from appropriate 5-arylmethyl-4-methoxypyrimidin-2(lH)-ones similarly as described for 5-phenyl derivatives. Antiviral activity was found for (S)-l-[3-hydroxy-2- (phosphonomethoxy)propyl]-5-phenyluracil (9a) (HSV-1 and HSV-2) and (R)-1-[3-hydroxy2-(phosphonomethoxy)propyl]-5-phenylcytosine (14) (cytomegalovirus and varicella-zoster virus), both tested in cell cultures. Some of the 5-phenyluracil derivatives possessed inhibitory activity against thymidine Phosphorylase from SD-lymphoma.