Synthetic approaches to DNMT inhibitor SGI-1027 and effects on the U937 leukemia cell line

Bioorg Med Chem Lett. 2013 Mar 15;23(6):1631-5. doi: 10.1016/j.bmcl.2013.01.085. Epub 2013 Jan 30.

Abstract

The known DNMT inhibitor SGI-1027 4 has been synthesized using as key steps Pd-catalyzed Ar-N bond formation reactions performed in a sequential or convergent manner. In the former approach, a by-product, which corresponds to the incorporation of two units of 4-chloroquinoline, was also isolated. The biological effects of compound 4 in the U937 human leukemia cell line are also described.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoquinolines / chemical synthesis
  • Aminoquinolines / chemistry*
  • Aminoquinolines / pharmacology
  • Catalysis
  • Cell Cycle Checkpoints / drug effects
  • DNA (Cytosine-5-)-Methyltransferases / antagonists & inhibitors*
  • DNA (Cytosine-5-)-Methyltransferases / metabolism
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Leukemia / enzymology
  • Leukemia / pathology
  • Palladium / chemistry
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry*
  • Pyrimidines / pharmacology
  • U937 Cells

Substances

  • Aminoquinolines
  • Enzyme Inhibitors
  • Pyrimidines
  • SGI-1027
  • Palladium
  • DNA (Cytosine-5-)-Methyltransferases