Novel benzoquinoline derivatives via unpredicted condensation of ethyl propiolate and naphthylamines: Synthesis and topoisomerase inhibition activity.
An unpredicted condensation of naphthylamine with two molecules of ethyl propiolate yields directly carbethoxy benzoquinoline in high yield. Some benzoquinoline carboxamide derivatives with protonatable side chains were then synthesized and evaluated for antiproliferative activity on human tumor cell lines. The most active compound (7a) demonstrated to intercalate into DNA and to inhibit the relaxation activity mediated by topoisomerase II.
Department of Pharmaceutical and Pharmacological Sciences, University of Padova, via Marzolo 5, 35131 Padova, Italy.
Giovanni
G
Marzaro
Department of Pharmaceutical and Pharmacological Sciences, University of Padova, via Marzolo 5, 35131 Padova, Italy.
Lisa
L
Dalla Via
Department of Pharmaceutical and Pharmacological Sciences, University of Padova, via Marzolo 5, 35131 Padova, Italy; Fondazione per la Biologia e la Medicina della Rigenerazione T.E.S.-Tissue Engineering and Signalling Onlus, Via F. Marzolo 13, 35131 Padova, Italy.
Aída Nelly
AN
García-Argáez
Department of Pharmaceutical and Pharmacological Sciences, University of Padova, via Marzolo 5, 35131 Padova, Italy.
Martina
M
Dalla Via
Department of Pharmaceutical and Pharmacological Sciences, University of Padova, via Marzolo 5, 35131 Padova, Italy. Electronic address: adriana.chilin@unipd.it.
Adriana
A
Chilin
D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000494:pharmacology; D045744:Cell Line, Tumor; D006801:Humans; D011422:Propionates / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry / Q000494:pharmacology*; D059005:Topoisomerase II Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*
D000480:Alkynes; D000588:Amines; D000970:Antineoplastic Agents; D011422:Propionates; D011804:Quinolines; D059005:Topoisomerase II Inhibitors; C544697:ethyl propiolate
Benzoquinolines; DNA; Microwave chemistry; Synthesis; Topoisomerase II