6244. Monastrol

Nomenclature

CAS number: 254753-54-3
1,2,3,4-Tetrahydro-4-(3-hydroxyphenyl)-6-methyl-2-thioxo-5-pyrimidinecarboxylic acid ethyl ester.
C14H16N2O3S; mol wt 292.35.
C 57.52%, H 5.52%, N 9.58%, O 16.42%, S 10.97%.

Description and references

Small molecule which inhibits mitotic kinesin motility protein, Eg5, thus preventing spindle assembly. Identification of activity: T. U. Mayer et al., Science 286, 971 (1999). Description of preparative technique: K. Lewandowski et al., J. Comb. Chem. 1, 105 (1999). X-ray structure determn and abs config: C. O. Kappe et al., Tetrahedron 56, 1859 (2000). Use as probe for mitotic mechanisms: T. M. Kapoor et al., J. Cell Biol. 150, 975 (2000).

Chemical structure

Properties

Colorless crystals from ethanol-hexane, mp 184-186°. Sol in DMSO.

Use

Inhibitor of mammalian cell mitosis.