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- W2950401935 abstract "Reaction of phosphoroorganic synthons with 8-azaadenine, 8-aza-2,6-diaminopurine, and 8-azaguanine using cesium carbonate yielded regioisomeric 8-azapurine N7-, N8-, and N9-(2-(phosphonomethoxy)alkyl) derivatives. This reaction followed by deprotection afforded isomeric 2-(phosphonomethoxy)ethyl (PME), (S)-(3-hydroxy-2-(phosphonomethoxy)propyl) [(S)-HPMP], (S)-(3-fluoro-2-(phosphonomethoxy)propyl) [(S)-FPMP], (S)-(2-(phosphonomethoxy)propyl) [(S)-PMP], and (R)-(2-(phosphonomethoxy)propyl) [(R)-PMP] derivatives. 13C NMR spectra were used for structural assignment of the regioisomers. None of the 8-isomers exhibited any antiviral activity against herpesviruses, Moloney murine sarcoma virus (MSV), and/or HIV. 9-(S)-HPMP-8-azaadenine (23) and PME-8-azaguanine (65) were active against HSV-1, HSV-2, and CMV at 0.2−7 μg/mL, VZV at 0.04−0.4 μg/mL, and MSV (at 0.3−0.6 μg/mL). PME-8-azaguanine (65) and (R)-PMP-8-azaguanine (71a) protected MT-4 and CEM cells against HIV-1- and HIV-2-induced cytopathicity at a concentration of ∼2 μg/mL." @default.
- W2950401935 created "2019-06-27" @default.
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- W2950401935 date "1996-01-01" @default.
- W2950401935 modified "2023-10-18" @default.
- W2950401935 title "Acyclic Nucleotide Analogs Derived from 8-Azapurines: Synthesis and Antiviral Activity" @default.
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- W2950401935 doi "https://doi.org/10.1021/jm960314q" @default.
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