Design and synthesis of novel 2-(3-substituted propyl)-3-(2-methyl phenyl) quinazolin-4-(3H)-ones as a new class of H1-antihistaminic agents

J Enzyme Inhib Med Chem. 2013 Feb;28(1):65-71. doi: 10.3109/14756366.2011.631184. Epub 2011 Nov 10.

Abstract

A series of novel 2-(3-substituted propyl)-3-(2-methyl phenyl) quinazolin-4-(3H)-ones were synthesized by the reaction of 2-(3-bromopropyl thio)-3-(2-methyl phenyl) quinazolin-4-(3H)-one with various amines. The starting material, 2-(3-bromopropyl thio)-3-(2-methyl phenyl) quinazolin-4-(3H)-one was synthesized from 2-methyl aniline. When tested for their in vivo H(1)-antihistaminic activity on conscious guinea pigs, all the test compounds protected the animals from histamine induced bronchospasm significantly. Compound 2-(3-(4-methylpiperazin-1-yl) propylthio)-3-(2-methyl phenyl) quinazolin-4(3H)-one (OT5) emerged as the most active compound (71.70% protection) of the series when compared to the reference standard chlorpheniramine maleate (70.09% protection). Compound OT5 shows negligible sedation (7%) compared to chlorpheniramine maleate (33%). Therefore, compound OT5 can serve as the leading molecule for further development into a new class of H(1)-antihistaminic agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bronchial Spasm / prevention & control
  • Chemistry Techniques, Synthetic
  • Chlorpheniramine / pharmacology
  • Drug Design
  • Drug Evaluation, Preclinical / methods
  • Guinea Pigs
  • Histamine H1 Antagonists / chemical synthesis*
  • Histamine H1 Antagonists / chemistry
  • Histamine H1 Antagonists / pharmacology*
  • Hypnotics and Sedatives / chemistry
  • Hypnotics and Sedatives / pharmacology
  • Male
  • Mice
  • Motor Activity / drug effects
  • Piperazines / pharmacology
  • Quinazolines / chemistry*
  • Quinazolinones / pharmacology
  • Structure-Activity Relationship

Substances

  • 2-(3-(4-methylpiperazin-1-yl)propylthio)-3-(2-methylphenyl)quinazolin-4(3H)-one
  • Histamine H1 Antagonists
  • Hypnotics and Sedatives
  • Piperazines
  • Quinazolines
  • Quinazolinones
  • Chlorpheniramine