Publications

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A series of omega-undecanoic amides of lup-20(29)-en-28-oic acid derivatives were synthesized and evaluated for activity in CEM 4 and MT-4 cell cultures against human immunodeficiency virus type 1 (HIV-1) strain IIIB/LAI. The potent HIV inhibitors which emerged, compounds 5a, 16a, and 17b, were all derivatives of betulinic acid (3beta-hydroxylup-20(29)-en-28-oic acid). No activity was found against HIV-2 strain ROD. Compound 5a showed no inhibition of HIV-1 reverse transcriptase activity with poly(C).oligo(dG) as template/primer, nor did it inhibit HIV-1 protease. Additional mechanistic studies revealed that this class of compounds interfere with HIV-1 entry in the cells at a postbinding step.

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Acyclo analogues of wyosine 2 and 3-methylguanosine 3, viz. 9-[(2-hydroxyethoxy)methyl]-3methyl-1, N-2-(prop-1 -ene-1,2-diyl)guanine 5a and 9-[(2-hydroxyethoxy)methyl]-3-methylguanine (3-methylacyclovir, 6a) were synthesized from acyclovir 4. The route to compound 5a involved methylation of the tricyclic acetate 7b with diazomethane-zinc iodide reagent and subsequent deacetylation; tricycle 5a was transformed into compound 6a with N-bromosuccinimide followed by ammonium hydroxide. Direct coupling of 3-methylguanine with the appropriate chain component resulted exclusively in formation of compound 9a, the N-7 regioisomer of 6a. The glycosidic hydrolysis rates of compounds 2 and 3 differed from those of the much less sterically compressed analogues 5a and 6a by less than one order of magnitude. This contrasts with the 105-fold increase in hydrolysis rate of compounds 2 and 3, compared with that of guanosine 1, and suggests that electronic factors must play an important role in the accelerated hydrolysis of 9-substituted 3-methylguanine derivatives. The antiviral activity of acyclovir was virtually abolished following N-3 methylation (6a). The other compounds (2, 3 and 5a) also failed to show any antiviral activity.

Abstract In order to study the influence of the position of both the carbamoyl and the D-ribofuranosylmoiety on the biological activity of pyridine-C-nucleosides, the 2-carbamoyl-5-P-D-ribofuranosylpyridine was synthesized.