Antonio R. Hergueta

Novel Carbocyclic Nucleosides Containing A Cyclobutyl Ring. Guanosine and Adenosine Analogues

(1R,cis)-2-(3-Amino-2,2-dimethylcyclobutyl)ethanol (4) was used as a precursor in the synthesis of cyclobutyl nucleoside analogues containing guanine, 8-azaguanine, adenine or 8-azaadenine. All the compounds were evaluated as antiviral agents in a variety of assay systems. Some activity was noted for compound 13, 17, 19 and 20 against vaccinia virus and for compounds 11, 12, 13, 17, 19 and 20 against herpes simplex virus, at concentrations that were up to 10-fold below the cytotoxic concentrations for the host cells.

Synthesis of a precursor of cyclobutane carbocyclic nucleosides from α-pinene

Abstract (+)-(1R,cis)-3-(Aminomethyl)-2,2-dimethylcyclobutylmethanol (4), a useful precursor for synthesis of analogues of Cyclobut-G, was prepared from (−)-(1S)-α-pmene (5) in five steps.

Unexpected anionically driven ring opening of a norbornene system

A norbornene moiety fused to a π-deficient heterocyclic system (quinoxaline) was found to undergo ring opening in a basic medium, possibly through a mechanism of retroaldol type.

MODIFIED CYCLOBUTANE CARBONUCLEOSIDES: SYNTHESIS AND EVALUATION OF THEIR ANTIVIRAL ACTIVITY

The synthesis of some 9-(2-cyclobutylethyl)guanine derivatives and analogous carbonucleosides from 1S-α-pinene is here presented. None of them showed detectable selectivity when assayed in the performed anti-viral tests.