Quinazoline-containing Hydrazydes of Dicarboxylic Acids and Products of Their Structural Modification: A Novel Class of Anti-inflammatory Agents

Acta Chim Slov. 2021 Jun;68(2):395-403.

Abstract

The synthesis of hydrazides formed by quinazolin-4(3H)-ylidenehydrazine and dicarboxylic acids, as well as their further modification are described in the present manuscript. It was shown that above-mentioned hydrazides may be obtained via acylation of initial quinazolin-4(3H)-ylidenehydrazine by corresponding acylhalides, cyclic anhydrides and imidazolides of dicarboxylic acids monoesters. Obtained hydrazides were converted into [1,2,4]triazolo[1,5-c]quinazolines that were used as initial compounds for chemical modification aimed to the introduction of amide fragment to the molecule. The IR, 1H NMR and chromato-mass spectral data of obtained compounds were studied and discussed. Obtained substances were studied for anti-inflammatory activity using carrageenan-induced paw inflammation model. Amides of ([1,2,4]triazolo[1,5-c]quinazoline-2-yl)alkyl carboxylic acids were detected as promising class of anti-inflammatory agents for further purposeful synthesis and profound study of anti-inflammatory activity.

MeSH terms

  • Administration, Oral
  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / administration & dosage
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / therapeutic use*
  • Carrageenan
  • Dicarboxylic Acids / administration & dosage
  • Dicarboxylic Acids / chemistry
  • Dicarboxylic Acids / therapeutic use*
  • Disease Models, Animal
  • Edema / chemically induced
  • Edema / drug therapy*
  • Hydrazines / administration & dosage
  • Hydrazines / chemistry
  • Hydrazines / therapeutic use*
  • Inflammation / chemically induced
  • Inflammation / drug therapy*
  • Quinazolines / administration & dosage
  • Quinazolines / chemistry
  • Quinazolines / therapeutic use*
  • Rats
  • Rats, Wistar

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Dicarboxylic Acids
  • Hydrazines
  • Quinazolines
  • Carrageenan