130427-53-1Relevant academic research and scientific papers
Nucleoside analogs
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, (2008/06/13)
Provided are compounds of the following formulae: A phosphonomethoxymethyoxymethyl purine/pyrimidine derivative of the formula STR1 wherein X and X' are the same or different and are hydrogen or alkyl. R and R' are the same or different and are hydrogen, alkyl, hydroxyalkyl or alkanoyl and B is a purine or pyrimidine base. A compound of formula (VI) STR2 wherein X is halogen, Y is S-phenyl, Se-phenyl or halogen and B is hypoxanthine, xanthine, guanine, 8-bromoguanine, 8-chloroguanine, 8-methylguanine, 8-thioguanine, 3-deazaguanine, purine, 2-aminopurine, 2,6-diaminopurine, adenine, 3-deazaadenine, 8-aminoguanine, 8-hydrazinoguanine, 8-hydroxyguanine, cytosine, 5-ethylcytosine, 5-methylcytosine, thymine, uracil, 5-chlorouracil, 5-bromouracil, 5-ethyluracil, 5-iodouracil, 5-propyluracil or 5-vinyluracil, 2-acetamido-6-diphenylcarbamoylpurine, 6-N-dimethylamino-methyladenine or 6-N-pivaloyladenine. A compound of formula (VII) STR3 wherein B is guanine, 8-guanine, 8-bromoguanine, 8-chloroguanine, 8-methylguanine, 8-thioguanine, 3-deazaguanine, 8-aminoguanine, 8-hydrazinoguanine, 8-hydroxyguanine, cytosine, 5-ethylcytosine, or 5-methylcytosine.
A Novel Synthesis of 1-OXA-HPMPA: A Potent Antiviral Agent Against Herpesviruses
Kim, Choung Un,Luh, Bing Y.,Martin, John C.
, p. 25 - 28 (2007/10/02)
A facile synthesis of 1-oxa-HPMPA 2 was achieved via a novel strategy of coupling 9-hydroxyadenine 13 and enol ether phosphonate 11.The newly synthesized 1-oxa analogue of HPMPA exhibited potent antiherpesvirus activity. Key words: HPMPA; 1-oxa-HPMPA; her
A New Class of Acyclic Phosphonate Nucleotide Analogues: Phosphonate Isosteres of Acyclovir and Ganciclovir Monophosphates as Antiviral Agents
Kim, Choung Un,Misco, Peter F.,Luh, Bing Yu,Hitchcock, Michael J. M.,Ghazzouli, Ismail,Martin, John C.
, p. 2286 - 2294 (2007/10/02)
Novel pohosphonate isosteres of acyclovir (ACV) and ganciclovir (DHPG) monophosphates (20 and 32) wre foudnd to be potent and selective antiherpesvirus agents.In the series of phosphonate analogues of ACV monophosphate, only the guanine analogue 20 exhibited activity against herpesviruses, similar to the structure-activity relationship observed for base modification of ACV analogues.The phosphonate isostere of ACV monophosphate (20) was more effective than ACV in the HSV-1 infected mouse model.The 3'-carba analogues of 9-purines/pyrimidines (adenine, HPMPA; guanine, HPMPG; cytosine, HPMPC) are devoid of antiherpesvirus activity.This result confirms that the β-oxygen atom of the phosphonomethyl ether functionality in HPMP-purines/pyrimidines plays a critical role for activity against herpesviruses.
Synthesis of a phosphonate isostere of ganciclovir monophosphate: A highly cytomegalovirus active phosphonate nucleotide analogue
Kim,Misco,Luh,Martin
, p. 3257 - 3260 (2007/10/02)
A novel synthetic methodology for the hydroxymethyl substituted acyclic acetal functionality was developed. The rationally designed phosphonate analogue 3 of ganciclovir monophosphate was highly active against human cytomegalovirus.
