Synthesis and anticancer activity of side chain analogs of the crambescidin alkaloids.
Twenty three side chain analogs of the crambescidin alkaloids were prepared from the corresponding pentacyclic zwitterionic core acid. In the crambescidin 800 and 657 series, potency increased with increasing chain length. In addition, substantial variations in tumor selectivity with structure were seen. Crambescidin analogs having short, nonpolar side chains were identified for the first time as promising anticancer agents.
Aron
Zachary D
ZD
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, CA 92697-2025, USA.
Pietraszkiewicz
Halina
H
Overman
Larry E
LE
Valeriote
Fredrick
F
Cuevas
Carman
C
D000470:Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D003114:Colony-Forming Units Assay; D019791:Guanidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D051381:Rats; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000494:pharmacology
D000470:Alkaloids; D000970:Antineoplastic Agents; D013141:Spiro Compounds; C490355:crambescidin 800; D019791:Guanidine