The enantiomers of carbocyclic 5'-norguanosine: activity towards Epstein-Barr virus.

  title={The enantiomers of carbocyclic 5'-norguanosine: activity towards Epstein-Barr virus.},
  author={Vasanthakumar P. Rajappan and Stewart W. Schneller and Stephanie L. Williams and Earl R. Kern},
  journal={Bioorganic \& medicinal chemistry},
  volume={10 4},


(±)‐1‐Deazaaristeromycin (4) has been reported to be an inactivator of S‐adenosylhomocysteine (AdoHcy) hydrolase and, as a consequence, to affect S‐adenosylmethionine (AdoMet) mediated macromolecular

Amino substituted derivatives of 5'-amino-5'-deoxy-5'-noraristeromycin.

Treatment of Venezuelan equine encephalitis virus infection with (-)-carbodine.

The 3-Deaza and 7-Deaza Derivatives of 5'-Amino-5'-deoxy-5'-noraristeromycin

Two Pd(0)-catalyzed allylic substitution reactions afforded the desired azide intermediates, 12 and 16 , which were transformed to target compounds by standard procedures, and found to be inactive except for weak effect against hepatitis B virus.



Antiviral enantiomeric preference for 5'-noraristeromycin.

The (-)-enantiomer retained the significant anticytomegalovirus properties previously reported for the racemic 2 and was, on the average, 10-fold more potent than (+)-2 in inhibiting virus replication, tumor cell growth, and (S)-adenosyl-L-homocysteine hydrolase activity.

Structure-activity relationships of L-dioxolane uracil nucleosides as anti-Epstein Barr virus agents.

In view of the potent antiviral activity plus favorable toxicity profiles, L-I-OddU may be potentially useful for the treatment of EBV-related infectious diseases as well as for delaying the onset or decreasing the incidence ofEBV-associated cancers.

Guanosine Analogues as Anti-Herpesvirus Agents

Guanosine analogues hold great promise, not only as antiviral agents for the treatment of herpesvirus infections, but also as antitumor agent for the combined gene therapy/chemotherapy of cancer, provided that (part of) the tumor cells have been transfected by the viral TK gene.

In Vitro Activities of Methylenecyclopropane Analogues of Nucleosides and Their Phosphoralaninate Prodrugs against Cytomegalovirus and Other Herpesvirus Infections

Evidence is provided for the high activity of some of these methylenecyclopropane analogues against various herpesviruses, particularly HCMV, in tissue culture and suggest that further evaluation is warranted to determine their potential for use in future clinical studies.

A 5′-Noraristeromycin Enantiomer with Activity Towards Hepatitis B Virus

Abstract (+)-5′-Noraristeromycin has selective activity against hepatitis B virus (HBV) replication in 2.2.15 cells in culture, while the (-) enantiomer was found to be inactive. A modified synthesis

Carbocyclic 5′‐norcytidine (5′‐norcarbodine)

In evalu ating 3 and 6 for antiviral potential against a number of viruses, compound 3 was found to have activity towards Epstein-Barr virus.

Enantiospecific Synthesis of 5′-Noraristeromycin and its 7-Deaza Derivative and A Formal Synthesis of (-)-5′-Homoaristeromycin

Subjecting 5 to treatment with porcine liver esterase led to an efficient preparation of a substituted cyclopentane precursor which, following literature precedence, can be converted into (-)-5′-homoaristeromycin.

Palladium-Catalyzed Enantioselective Synthesis of Carbanucleosides

A general strategy has been developed for enantioselective synthesis of diverse carbanucleosides. The key step is a Pd(0)-catalyzed enantioselective allylic amination of

(±)-5′-Nor ribofuranoside carbocyclic guanosine

The synthesis of the guanine derivative (±)-2-amino-1,9-dihydro-9-[(1′α,2′β,3′β,4′α)-(2′,3′,4′-trihydroxy-1′-cyclopentyl]-6H-purin-6-one (2) is described. This compound is viewed as the carbocyclic