Total synthesis of isoprekinamycin: structural evidence for enhanced diazonium ion character and growth inhibitory activity toward cancer cells.

Abstract

The structurally novel diazobenzo[a]fluorene antibiotic isoprekinamycin (IPK) has been synthesized for the first time employing a Suzuki coupling of a brominated AB ring synthon with a boronate ester representing the D ring, followed by anionic cyclization and appropriate functional group manipulations. The first indication that the diazobenzo[a]fluorene system exhibits in vitro anticancer activity is provided and X-ray crystallographic evidence for enhancement of diazonium ion character as a consequence of intramolecular H-bonding is described.

• Authors: Wei Liu, Matthew Buck, Nan Chen, Muhong Shang, Nicholas J Taylor, Jalil Asoud, Xing Wu, Brian B Hasinoff, Gary I Dmitrienko
• Journal: Organic letters (Org Lett) Vol. 9 Issue 15 Pg. 2915-8 (Jul 19 2007) ISSN: 1523-7060 [Print] United States
• PMID: 17585773 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Diazonium Compounds
• Fluorenes
• isoprekinamycin

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Cell Division (drug effects)
• Cell Line, Tumor
• Crystallography, X-Ray
• Cyclization
• Diazonium Compounds (chemistry)
• Fluorenes (chemical synthesis, chemistry, pharmacology)
• Humans
• Hydrogen Bonding
• Molecular Structure