Synthesis and G-quadruplex stabilizing properties of a series of oxazole-containing macrocycles.
The synthesis of 24-membered macrocycles containing four, six, and seven oxazole moieties is described. Selected compounds were evaluated for their ability to specifically bind and stabilize G-quadruplex DNA and for cytotoxic activity. An unexpected oxidative cleavage reaction afforded a macrocyclic imide that was also evaluated for G-quadruplex stabilizing and cytotoxic activity.
Minhas
Gurpreet Singh
GS
Department of Pharmaceutical Chemistry, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, Piscataway, NJ 08854-8020, USA.
Pilch
Daniel S
DS
Kerrigan
John E
JE
LaVoie
Edmond J
EJ
Rice
Joseph E
JE
D004247:DNA / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D047028:Macrocyclic Compounds; D010080:Oxazoles; D004247:DNA