Synthesis and antitumor activity of novel amsacrine analogs: the critical role of the acridine moiety in determining their biological activity.
A new series of N-[4-(2'-oxo-2H-pyrano[2,3-b]quinolin-5'-ylamino)-phenyl]-methanesulfonamides was prepared and analyzed as novel amsacrine-like derivatives. Our preliminary biological evaluation has shown that the replacement of the acridine moiety with the analogous 2-oxo-2H-pyrano[2,3-b]quinoline system drastically reduced both their anticancer activity and their propency to intercalate into double stranded DNA.
Chilin
Adriana
A
Department of Pharmaceutical Sciences, University of Padova, Via Marzolo, 5, 35131 Padova, Italy. adriana.chilin@unipd.it
Marzaro
Giovanni
G
Marzano
Christine
C
Dalla Via
Lisa
L
Ferlin
Maria Grazia
MG
Pastorini
Giovanni
G
Guiotto
Adriano
A
D000677:Amsacrine / Q000031:analogs & derivatives*; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004247:DNA / Q000378:metabolism; D006801:Humans; D007364:Intercalating Agents; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000494:pharmacology
D000970:Antineoplastic Agents; D007364:Intercalating Agents; D013449:Sulfonamides; D000677:Amsacrine; D004247:DNA