C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
Four enantiomerically pure monoseco-analogues, 5, 7, 9, and 11, of the phenanthroquinolizidine alkaloid julandine (1) and four of congener cryptopleurine (2), viz. compounds 6, 8, 10, and 12, have been prepared and subjected to preliminary biological evaluation. These analogues show dramatically reduced cytotoxicity compared with the parent system 2 but they are, nevertheless, potent anti-angiogenic agents.
Banwell
Martin G
MG
Research School of Chemistry, The Australian National University, Canberra ACT 0200, Australia. mgb@rsc.anu.edu.au
Bezos
Anna
A
Burns
Christopher
C
Kruszelnicki
Irma
I
Parish
Christopher R
CR
Su
Stephen
S
Sydnes
Magne O
MO
D000470:Alkaloids / Q000737:chemistry* / Q000494:pharmacology; D020533:Angiogenesis Inhibitors / Q000494:pharmacology; D000818:Animals; D001011:Aorta / Q000187:drug effects; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor / Q000379:methods; D006801:Humans; D020128:Inhibitory Concentration 50; D051379:Mice; D008956:Models, Chemical; D010618:Phenanthrolines / Q000737:chemistry* / Q000494:pharmacology; D011807:Quinolizines / Q000737:chemistry* / Q000494:pharmacology; D051381:Rats; D013237:Stereoisomerism; D013267:Stilbenes / Q000494:pharmacology
D000470:Alkaloids; D020533:Angiogenesis Inhibitors; D010618:Phenanthrolines; D011807:Quinolizines; D013267:Stilbenes; C508742:julandine; C007160:cryptopleurine; C058728:fosbretabulin