3-arylamino and 3-alkoxy-nor-beta-lapachone derivatives: synthesis and cytotoxicity against cancer cell lines.
Several 3-arylamino and 3-alkoxy-nor-beta-lapachone derivatives were synthesized in moderate to high yields and found to be highly potent against cancer cells SF295 (central nervous system), HCT8 (colon), MDA-MB435 (melanoma), and HL60 (leukemia), with IC(50) below 2 microM. The arylamino para-nitro and the 2,4-dimethoxy substituted naphthoquinones showed the best cytoxicity profile, while the ortho-nitro and the 2,4-dimethoxy substituted ones were more selective than doxorubicin and similar to the precursor lapachones, thus emerging as promising new lead compounds in anticancer drug development.
da Silva
Eufrânio N
EN
Instituto de Quimica, Universidade de Brasilia, 70910-970 Brasilia, DF, Brazil.
de Deus
Clara F
CF
Cavalcanti
Bruno C
BC
Pessoa
Cláudia
C
Costa-Lotufo
Letícia V
LV
Montenegro
Raquel C
RC
de Moraes
Manoel O
MO
Pinto
Maria do Carmo F R
Mdo C
de Simone
Carlos A
CA
Ferreira
Vitor F
VF
Goulart
Marilia O F
MO
Andrade
Carlos Kleber Z
CK
Pinto
Antônio V
AV
D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D009285:Naphthoquinones; C014638:beta-lapachone