Synthesis and biological evaluation of N-(arylsulfanyl)carbonyl analogues of paclitaxel (Taxol)


Karliga B., Schilling J., Kingston D., Bane S., Ravindra R., Talinli N.

CHEMISTRY & BIODIVERSITY, vol.3, no.4, pp.396-404, 2006 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 3 Issue: 4
  • Publication Date: 2006
  • Doi Number: 10.1002/cbdv.200690043
  • Title of Journal : CHEMISTRY & BIODIVERSITY
  • Page Numbers: pp.396-404

Abstract

Four new N-(arylsufanyl)carbonyl paclitaxel analogues (2a-d) were prepared from 7-(triethylsilyl)protected baccatin III (5). Their cytotoxicities against human ovarian (A2780) and prostate cancer (PC3) cell lines, as well as their tubulin-assembly activities, were determined. In these assays, the new compounds showed rather weak activities, one two orders of magnitude below those of paclitaxel (taxol, 1). The known 3'-N-[(thiophen-2-yl)carbonyl] paclitaxel analogue 3 was also prepared. As previously reported, 3 exhibited strongly improved cytotoxicities and tubulin-assembly activities as compared to paclitaxel (1).