New 1,2,3,4-tetrahydro-1-aza-anthraquinones and 2-aminoalkyl compounds from norlapachol with molluscicidal activity.
New nitrogen derivatives from norlapachol, including four new diastereomeric 1,2,3,4-tetrahydro-1-aza-anthraquinones obtained from the Prins cyclization on suitable aminoacetaldehyde dimethylacetal derivatives with formic acid, were found to exhibit molluscicidal activity against Biomphalaria glabrata. These derivatives showed low to medium LC(50) values, similar to those reported previously for the homologous series of nitrogen derivatives of lapachol. The toxicity profile against Artemia salina was also determined for all compounds.
Barbosa
Ticiano P
TP
Laboratório de Tecnologia Farmacêutica, LTF-UFPB, Campus I, Cidade Universitária, João Pessoa, Brazil.
Camara
Celso A
CA
Silva
Tania M S
TM
Martins
Rodrigo M
RM
Pinto
Angelo C
AC
Vargas
Maria D
MD
D000478:Alkylation; D000586:Amination; D000818:Animals; D000880:Anthraquinones / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D006900:Hydroxylation; D015394:Molecular Structure; D008974:Mollusca / Q000187:drug effects*; D008975:Molluscacides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D009285:Naphthoquinones / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000880:Anthraquinones; D001372:Aza Compounds; D008975:Molluscacides; D009285:Naphthoquinones; C506865:norlapachol