178918-38-2

Upstream product

• 169514-92-5 [1-(2,6-Diamino-purin-9-ylmethyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester 
• 160308-67-8 9-(3-phthalimido-2-hydroxypropyl)-2,6-diaminopurine 
• 169514-90-3 N'-{2-Amino-9-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxy-propyl]-9H-purin-6-yl}-N,N-dimethyl-formamidine 

Relevant academic research and scientific papers

Synthesis of 2'-aminomethyl derivatives of N-(2- (phosphonomethoxy)ethyl) nucleotide analogues as potential antiviral agents

A series of purine and pyrimidine N-(2-(phosphonomethoxy)ethyl) derivatives bearing aminomethyl, (dimethylamino)methyl, morpholinomethyl, and (trimethylammonio)methyl groups at the 2'-position were synthesized. The compounds were prepared by alkylation of the heterocyclic bases with appropriately substituted (aminoalkyl)oxiranes followed by condensation of the resulting intermediates with dialkyl ((p- tolylsulfonyl)oxy)methanephosphonate and subsequent treatment of the obtained diester with bromotrimethylsilane. 9-(3-Amino-2- (phosphonomethoxy)propyl)adenine (2a) proved active against varicella zoster virus (VZV), cytomegalovirus (CMV), and Moloney murine sarcoma virus (MSV) in the concentration range of 7-35 μg/mL. None of the other aminoalkyl derivatives demonstrated significant antiviral activity against herpes simplex virus type 1 and 2 (HSV-1 and HSV-2), VZV, (CMV), vaccinia virus (VV), MSV, and human immunodeficiency virus type 1 and 2 (HIV-1 and HIV-2).

Acyclic nucleotide analogues and related compounds

Acyclic nucleotide analogues bearing amino- and N-substituted amino groups in the side chain were prepared by alkylation of the bases with corresponding oxiranes and subsequent introduction of phosphonomethyl ether function. Novel enantiomeric synthons for the preparation of HPMP-compounds were prepared from a common intermediate and applied to syntheses of novel compounds (e.g. 8-azaguanine derivatives).