Syntheses and anti-depressant activity of 5-amino-1, 3, 4-thiadiazole-2-thiol imines and thiobenzyl derivatives

Bioorg Med Chem. 2008 Sep 1;16(17):8029-34. doi: 10.1016/j.bmc.2008.07.056. Epub 2008 Jul 24.

Abstract

A number of new imine derivatives of 5-amino-1, 3, 4-thiadiazole-2-thiol have been synthesized, and their anti-depressant activity was tested using imipramine as reference drug. Two compounds namely 5-{[1-(4-chlorophenyl)-3-(4-methoxy-phenyl)prop-2-en-1-ylidene]-amino}-5-benzylthio-1, 3,4 -thiadiazole 4i(b) and 5-{[1-(4-chlorophenyl)-3-(4-dimethyl-aminophenyl)-prop-2-en-1-ylidene]amino}-5-benzylthio-1,3,4-thiadiazole 4i(c) have shown significant anti-depressant activity, which decreased immobility time by 77.99% and 76.26% compared to the standard imipramine (82%). All the compounds in the series have passed neurotoxicity tests.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antidepressive Agents / chemical synthesis*
  • Antidepressive Agents / chemistry
  • Antidepressive Agents / pharmacology*
  • Behavior, Animal / drug effects
  • Dose-Response Relationship, Drug
  • Drug Evaluation, Preclinical
  • Imines / chemical synthesis*
  • Imines / chemistry
  • Imines / pharmacology*
  • Imipramine / pharmacology
  • Male
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Motor Activity / drug effects
  • Stereoisomerism
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry
  • Sulfhydryl Compounds / pharmacology*
  • Swimming
  • Thiadiazoles / chemical synthesis*
  • Thiadiazoles / chemistry
  • Thiadiazoles / pharmacology*

Substances

  • Antidepressive Agents
  • Imines
  • Sulfhydryl Compounds
  • Thiadiazoles
  • Imipramine