Synthesis and G-quadruplex stabilizing properties of a series of oxazole-containing macrocycles

• Published in: Bioorganic & medicinal chemistry letters Vol. 16; no. 15; pp. 3891 - 3895
• Main Authors: Minhas, Gurpreet Singh, Pilch, Daniel S., Kerrigan, John E., LaVoie, Edmond J., Rice, Joseph E.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.08.2006; Elsevier
• Subjects: Biological and medical sciences; Cytotoxicity; DNA - chemistry; G-quadruplex; Macrocycles; Macrocyclic Compounds - chemical synthesis; Macrocyclic Compounds - chemistry; Medical sciences; Miscellaneous; Oxazoles; Oxazoles - chemistry; Pharmacology. Drug treatments; Spectrophotometry, Ultraviolet; Synthesis; Cytotoxicity; Synthesis; Oxazoles; Macrocycles; G-quadruplex; Sequence specificity; Nucleotide sequence; Stabilization; Molecular interaction; In vitro; Telomere; Biological activity; Guanine; Macrocycle; Imide; Biological fixation; DNA; Cleavage; Oxidation; Chemical synthesis; Oxazole derivatives
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2006.05.038

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. 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.