84408-37-7Relevant academic research and scientific papers
Conversion of guanosine into acyclovir and its 6-deoxy derivative
Buck, Ildiko M.,Eleuteri, Alessandra,Reese, Colin B.
, p. 9195 - 9206 (2007/10/02)
2-amino-6-(4-chlorophenylthio)-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl) purine 11, which is readily prepared by allowing the corresponding 6-chloro-compound 10 to react with 4-chloro(thiophenol) and triethylamine in methanol solution at room temperature, reacts with boron trifluoride diethyl etherate in boiling dichloromethane solution to give 2-amino-6-(4-chlorophenylthio)-9H-purine 12 in high isolated yield. 9-[(2-acetoxyethoxy)methyl]-2-amino-6-(4-chlorophenylthio)-9H-purine 13, prepared from the latter aglycone 12 in good yield, is converted by a four-step process into acyclovir 1 and by a two-step process into 6-deoxyacyclovir 2.
Process for preparing purine derivates
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, (2008/06/13)
There is disclosed a process for preparing purine derivatives of the formula I wherein, R1 represents hydrogen, CH3CO or a higher acyl,R3 represents hydrogen, CH3CO or a higher acyl, CF3CO, CCl3CO, PhCO or CH2 AR, such as benzyl or substituted benzyl, and benzoisothiazolyl-S,S-dioxide, and, Z represents OH, hydrogen or halo. Said compounds are either drugs or prodrugs for the treatment of herpes infections. There are also disclosed some novel compounds of formula I useful as prodrugs.
Preparative electrochemical reduction of 2-amino-6-chloropurine and synthesis of 6-deoxyacyclovir, a fluorescent substrate of xanthine oxidase and a prodrug of acyclovir.
Kusmierek,Czochralska,Johansson,Shugar
, p. 701 - 707 (2007/10/02)
D.c. polarography of 2-amino-6-chloropurine in aqueous medium over a broad pH range revealed two diffusion waves, the first of which corresponds to reduction of the C(6)-Cl bond, leading to formation of 2-aminopurine in high yield. Condensation of the sodium salt of 2-aminopurine with (2-acetoxyethoxy)methyl chloride led to the two isomeric 9- and 7-(2-hydroxyethoxymethyl)-2-aminopurines. The 9- isomer, 6-deoxyacyclovir, a prodrug of acyclovir previously synthesized by another route, was readily converted to the latter by xanthine oxidase; the 7-isomer was not a substrate. The intense fluorescence of 6-deoxyacyclovir makes it a convenient fluorescent substrate for xanthine oxidase, although less sensitive than xanthine; it is shown that 2-aminopurine would be a very sensitive fluorescent substrate. The polarographic behaviour of the riboside of 2-amino-6-chloropurine was virtually identical with that of the parent purine, leading to a simple procedure for conversion of 2-amino-6-chloropurine nucleosides and acyclonucleosides to the corresponding 2-aminopurine congeners.
Method of producing acyclovir
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, (2008/06/13)
The novel compound 6-deoxyacyclovir is enzymatically converted to acyclovir by xanthine oxidase/dehydrogenase or aldehyde oxidase in vivo, i.e. within the body of the animal being treated. The enzymatic conversion may also be effected ex vivo (i.e. in vitro) as a method of synthesizing acyclovir.
