Synthesis, properties, and perspectives of gem-diphosphono substituted-thiazoles

Eur J Med Chem. 2008 May;43(5):1015-24. doi: 10.1016/j.ejmech.2007.07.005. Epub 2007 Jul 27.

Abstract

A series of substituted arylidene thiazoles were allowed to react with Wittig-Horner (WH) reagent, tetraethyl methyl-1,1-bisphosphonate, to produce via Michael addition reaction the corresponding heteroarylmethylenebisphosphonates (BPs) in different yields according to the experimental conditions. Acid hydrolysis of the new BPs was undertaken to obtain the corresponding bisphosphonic acids. Prediction and the in vivo activity of the products in the rat adjuvant model are also discussed in terms of structure-activity relationships (SAR).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Bone Density Conservation Agents / chemical synthesis*
  • Bone Density Conservation Agents / chemistry
  • Bone Density Conservation Agents / pharmacology
  • Bone Resorption / drug therapy
  • Chronic Disease
  • Diphosphonates / chemical synthesis*
  • Diphosphonates / chemistry
  • Diphosphonates / pharmacology
  • Granuloma / drug therapy
  • Hypersensitivity, Delayed / drug therapy
  • Inflammation / drug therapy
  • Mice
  • Rats
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry
  • Thiazoles / pharmacology

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Bone Density Conservation Agents
  • Diphosphonates
  • Thiazoles