Synthesis and evaluation of thiophenyl derivatives as inhibitors of alkaline phosphatase

Bioorg Med Chem Lett. 2011 Apr 15;21(8):2297-301. doi: 10.1016/j.bmcl.2011.02.089. Epub 2011 Mar 21.

Abstract

Pathological calcifications induced by deposition of basic phosphate crystals or hydroxyapatite (HA) on soft tissues are a large family of diseases comprising of ankylosing spondylitis (AS), end-stage osteoarthritis (OA) and vascular calcification. High activity of tissue non-specific alkaline phosphatase (TNAP) is a hallmark of pathological calcifications induced by HA deposition. The use of TNAP inhibitor is a possible therapeutic option to address calcific diseases produced by HA deposition on soft tissues. We report the synthesis of a series of thiopheno-imidazo[2,1-b]thiazole derivatives which were evaluated as potential inhibitors of TNAP displaying a large range of IC(50) at pH 10.4 (from 42±13 μM to more than 800 μM).

MeSH terms

  • Alkaline Phosphatase / antagonists & inhibitors*
  • Alkaline Phosphatase / metabolism
  • Calcinosis / drug therapy
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / therapeutic use
  • Humans
  • Hydrogen-Ion Concentration
  • Phenols / chemical synthesis
  • Phenols / chemistry*
  • Phenols / therapeutic use
  • Sulfhydryl Compounds / chemical synthesis
  • Sulfhydryl Compounds / chemistry*
  • Sulfhydryl Compounds / therapeutic use
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / therapeutic use

Substances

  • Enzyme Inhibitors
  • Phenols
  • Sulfhydryl Compounds
  • Thiazoles
  • thiophenol
  • Alkaline Phosphatase