(-)-(cis)-4-(2-Amino-9H-purin-9-yl)-2-cyclopentenyl carbinol (6-deoxycarbovir) was prepared in order to evaluate prodrug approaches to increased bioavailability of the anti-HIV agent, (-)-carbovir. Incubation experiments demonstrated that 6-deoxycarbovir was rapidly converted to (-)-carbovir by the enzyme, xanthine oxidase. Since xanthine oxidase activity is present in both the intestine and liver, a high first pass conversion to carbovir would be expected in vivo.
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Acknowledgment. This work was supported by Public Health Service Grant CA23263 from the National Cancer Institute.