Design, synthesis, and evaluation of analogues of (+)-14-normethyldiscodermolide.
[Structure: see text] The design, syntheses, and biological evaluation of nine totally synthetic analogues of the microtubule-stabilizing agent (+)-14-normethyldiscodermolide (2) are reported. Simplification at the C(21)-C(24) terminal diene and at the C(1)-C(5) lactone moieties reveals significant structure-activity relationships.
Smith
Amos B
AB
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Freeze
B Scott
BS
Lamarche
Matthew J
MJ
Hirose
Tomoyasu
T
Brouard
Ignacio
I
Xian
Ming
M
Sundermann
Kurt F
KF
Shaw
Simon J
SJ
Burlingame
Mark A
MA
Horwitz
Susan Band
SB
Myles
David C
DC
D000475:Alkenes / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D045744:Cell Line, Tumor; D006801:Humans; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship
C511441:14-normethyldiscodermolide; D000475:Alkenes; D000970:Antineoplastic Agents; D002219:Carbamates; D007783:Lactones; D011753:Pyrones