A class of novel Schiff's bases: Synthesis, therapeutic action for chronic pain, anti-inflammation and 3D QSAR analysis

Bioorg Med Chem. 2010 Mar 15;18(6):2165-2172. doi: 10.1016/j.bmc.2010.01.075. Epub 2010 Feb 6.

Abstract

To discover analgesics for treating chronic pain 17 novel Schiff's bases, N,N'-(Z-allylidene-1,3-diyl)bisamino acid methyl esters were prepared from 1,1,3,3,-tetramethoxypropane and amino acid methyl esters. On tail-flick mouse model 20 micromol/kg of these Schiff's bases were orally administered, the analgesic action started 30 min after administration, reached the maximum 120 min after administration, and at 180 min this action was still observed. On a xylene-induced ear edema mouse model 20 micromol/kg of these Schiff's bases exhibited desirable anti-inflammation. Thus the present Schiff's bases are able to treat chronic pain from inflammation. The effect of the side chains of the amino acid residues of these Schiff's bases on the analgesic activity was explained with 3D QSAR.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Oral
  • Animals
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / classification
  • Anti-Inflammatory Agents / therapeutic use*
  • Chronic Disease
  • Disease Models, Animal
  • Ear / pathology
  • Edema / chemically induced
  • Edema / drug therapy*
  • Edema / pathology
  • Esters / chemical synthesis
  • Esters / chemistry
  • Male
  • Mice
  • Mice, Inbred ICR
  • Models, Molecular
  • Molecular Structure
  • Pain / drug therapy*
  • Quantitative Structure-Activity Relationship
  • Schiff Bases / chemistry*
  • Schiff Bases / classification
  • Schiff Bases / therapeutic use*
  • Stereoisomerism
  • Xylenes

Substances

  • Anti-Inflammatory Agents
  • Esters
  • Schiff Bases
  • Xylenes