Clitocine, [6-amino-5-nitro-(beta-D-ribofuranosylamino)pyrimidine] a natural nucleoside isolated by the mushroom Clitocybe inversa, has shown strong insecticidal activity and potent cytostatic effects against several leukemia cell lines. It was found to be a substrate and inhibitor of adenosine kinase. The carbocyclic clitocine analogue 2 was also found to be readly phophorylated by adenosine kinase and significantly active both in vitro and in vivo against influenza A virus (Singapore). The observation that, from the structural point of view, clitocine shows a biogenetic relationship with adenosine, prompted us to prepare analogues of the anti-HIV agents 2'.3'-dideoxy-3'-oxoadenosine (isoddA) and 9-[phosphonomethoxy)ethyl]adenine (PMEA), in which the adenine moiety is replaced from 4,6-diamino-5-nitropyrimidine, the clitocine aglycon. Synthesis, antiviral activity and structure-activity relathionships of the title compounds will be reported.

Synthesis and anti-HIV activity of isonucleosides and acyclic nucleotides related to clitocine

FRANCHETTI, Palmarisa;CAPPELLACCI, Loredana;GRIFANTINI, Mario;
1994-01-01

Abstract

Clitocine, [6-amino-5-nitro-(beta-D-ribofuranosylamino)pyrimidine] a natural nucleoside isolated by the mushroom Clitocybe inversa, has shown strong insecticidal activity and potent cytostatic effects against several leukemia cell lines. It was found to be a substrate and inhibitor of adenosine kinase. The carbocyclic clitocine analogue 2 was also found to be readly phophorylated by adenosine kinase and significantly active both in vitro and in vivo against influenza A virus (Singapore). The observation that, from the structural point of view, clitocine shows a biogenetic relationship with adenosine, prompted us to prepare analogues of the anti-HIV agents 2'.3'-dideoxy-3'-oxoadenosine (isoddA) and 9-[phosphonomethoxy)ethyl]adenine (PMEA), in which the adenine moiety is replaced from 4,6-diamino-5-nitropyrimidine, the clitocine aglycon. Synthesis, antiviral activity and structure-activity relathionships of the title compounds will be reported.
1994
275
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11581/242206
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? ND
social impact