Studies on quinones. Part 37. Synthesis and biological activity of o-aminoester functionalised benzo- and naphtho[2,3-b]thiophenequinones.
The synthesis of 3-amino-2-methoxycarbonyl-4,7-dimethoxybenzo[b]thiophene (5) and benzothieno[3,2-d][1,3]oxazin 15 from 3,6-dimethoxy-2-nitrobenzaldehyde (1) is reported. Benzo[b]thiophene-4,7-quinones 9 and 10 were prepared in good yields by oxidative deprotection of the corresponding dimethoxybenzothiophenes 8 and 7. Cycloaddition reaction of quinone 8 with 1-(E)-trimethylsilyloxy-1,3-butadiene followed by acid-induced aromatization provides access to naphtho[2,3-b]thiophene-4,9-quinone 13 and 14. The in vitro activity of the new quinones against Leishmania amazonensis and human-T-cell leukemia virus type 1 (HTLV-1) is reported.
Valderrama
Jaime A
JA
Facultad de Química, Pontificia Universidad Católica de Chile, Santiago. jvalderr@puc.cl
Astudillo
Claudio
C
Tapia
Ricardo A
RA
Prina
Eric
E
Estrabaud
Emilie
E
Mahieux
Renaud
R
Fournet
Alain
A
D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D016227:Benzoquinones / Q000138:chemical synthesis* / Q000494:pharmacology*; D002455:Cell Division / Q000187:drug effects; D002460:Cell Line; D015368:Human T-lymphotropic virus 1 / Q000187:drug effects; D006801:Humans; D007202:Indicators and Reagents; D007894:Leishmania mexicana / Q000187:drug effects; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000494:pharmacology*
D000981:Antiprotozoal Agents; D000998:Antiviral Agents; D016227:Benzoquinones; D007202:Indicators and Reagents; D009285:Naphthoquinones