Synthesis and configurational assignment of 1,2-dihydroimidazo[5,1-b] quinazoline-3,9-diones: Novel NMDA receptor antagonists

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Abstract

NMDA receptors form a major subdivision of the ionotropic glutamate receptor family that mediates excitatory synaptic transmission in the brain. Series of 1-substituted 1,2-dihydroimidazo[5,1-b]quinazolinediones were synthesized and found to have potent nanomolar activity at the glycine site of the NMDA receptor. Imidazoquinazolinediones were prepared by cyclocondensation of 4-oxo-quinazoline-2-carboxamide with aldehydes and orthoesters with good yields. The formed enantiomers were separated by chiral HPLC. The absolute configuration of pure enantiomers is elucidated by combined CD/Quantumchemical time-dependent DFT calculation method (TDDFT).

Original languageEnglish
Pages (from-to)10365-10371
Number of pages7
JournalTetrahedron
Volume68
Issue number50
DOIs
Publication statusPublished - Dec 16 2012

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Keywords

  • Absolute configuration
  • HPLC-ECD
  • NMDA antagonist
  • Quinazoline
  • TDDFT ECD calculation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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