New mannose derivatives: The tetrazole analogue of mannose-6-phosphate as angiogenesis inhibitor

Bioorg Med Chem Lett. 2016 Jan 15;26(2):636-639. doi: 10.1016/j.bmcl.2015.11.059. Epub 2015 Nov 18.

Abstract

Two novel compounds with mannose-derived structure, bearing a tetrazole (compound 3) and a sulfone group (compound 4) in terminal position, have been prepared from methyl α-d-mannopyranoside in reduced number of steps. The angiogenic activity of 3 and 4 has been screened using the chick chorioallantoic membrane (CAM) method. Tetrazole 3 has been identified to possess a promising bioactivity, being identified as angiogenesis inhibitor, with 68% of neovascular vessels when compared to control (PBS).

Keywords: Carboxylic acid; Iodination; Mannose-6-phosphate analogues; Sulfone; Tetrazole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiogenesis Inhibitors / chemistry*
  • Angiogenesis Inhibitors / pharmacology*
  • Animals
  • Chickens
  • Chorioallantoic Membrane / blood supply
  • Chorioallantoic Membrane / drug effects
  • Halogenation
  • Mannosephosphates / chemistry*
  • Mannosephosphates / pharmacology*
  • Models, Molecular
  • Structure-Activity Relationship
  • Sulfones / chemistry
  • Sulfones / pharmacology
  • Tetrazoles / chemistry*
  • Tetrazoles / pharmacology*

Substances

  • Angiogenesis Inhibitors
  • Mannosephosphates
  • Sulfones
  • Tetrazoles
  • 1H-tetrazole
  • mannose-6-phosphate