Synthesis and antiviral evaluation of isatin ribonucleosides.
A series of novel substituted isatin ribonucleosides 3b-3f were synthesized in good yields by a TMSOTf catalysed coupling reaction between the silylated nitrogenated base (1b-1f) and 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (2). Isatin nucleoside 3a previously reported was also prepared using this method giving high yield. From the compounds tested, ribonucleoside 3f proved to be the most active one when assayed for antiviral activitiy on HSV-1 infected cells, leading to 66% of inhibition of virus yield. All the isatin derivatives tested did not inhibit HIV-1 Reverse Transcriptase (RT) activity.
de Oliveira
Mara R P
MR
Universidade Federal do Rio de Janeiro, Instituto de Química, Departamento de Química Orgânica, Ilha do Fundão, CEP 21945-970, Rio de Janeiro, Brazil.
Torres
José C
JC
Garden
Simon J
SJ
dos Santos
Carla Veronica B
CV
Alves
Thatyana Rocha
TR
Pinto
Angelo C
AC
Pereira
Helena de S
Hde S
Ferreira
Luiz Roberto Leão
LR
Moussatché
Nissin
N
Frugulhetti
Izabel Christina de P P
IC
Ferreira
Vitor F
VF
de Souza
Maria Cecília B V
MC
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D015195:Drug Design; D054303:HIV Reverse Transcriptase / Q000378:metabolism; D018259:Herpesvirus 1, Human / Q000187:drug effects; D007510:Isatin / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000998:Antiviral Agents; D012263:Ribonucleosides; D007510:Isatin; D054303:HIV Reverse Transcriptase