Synthetic approaches, functionalization and therapeutic potential of quinazoline and quinazolinone skeletons: the advances continue

Eur J Med Chem. 2015 Jan 27:90:124-69. doi: 10.1016/j.ejmech.2014.10.084. Epub 2014 Nov 5.

Abstract

The presence of N-heterocycles as an essential structural motif in a variety of biologically active substances has stimulated the development of new strategies and technologies for their synthesis. Among the various N-heterocyclic scaffolds, quinazolines and quinazolinones form a privileged class of compounds with their diverse spectrum of therapeutic potential. The easy generation of complex molecular diversity through broadly applicable, cost-effective, practical and sustainable synthetic methods in a straightforward fashion along with the importance of these motifs in medicinal chemistry, received significant attention from researchers engaged in drug design and heterocyclic methodology development. In this perspective, the current review article is an effort to recapitulate recent developments in the eco-friendly and green procedures for the construction of highly challenging and potentially bioactive quinazoline and quinazolinone compounds in order to help medicinal chemists in designing and synthesizing novel and potent compounds for the treatment of different disorders. The key mechanistic insights for the synthesis of these heterocycles along with potential applications and manipulations of the products have also been conferred. This article also aims to highlight the promising future directions for the easy access to these frameworks in addition to the identification of more potent and specific products for numerous biological targets.

Keywords: Bioactive heterocycles; Biological potential; Cross-coupling reactions; Enzymes; Inhibitors; Synthetic methods.

Publication types

  • Review

MeSH terms

  • Angiogenesis Inhibitors / chemical synthesis
  • Angiogenesis Inhibitors / chemistry
  • Angiogenesis Inhibitors / pharmacology
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Anticonvulsants / chemical synthesis
  • Anticonvulsants / chemistry
  • Anticonvulsants / pharmacology
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Proliferation / drug effects
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Glucuronidase / antagonists & inhibitors
  • Glucuronidase / metabolism
  • Humans
  • Molecular Structure
  • Phosphotransferases / antagonists & inhibitors
  • Phosphotransferases / metabolism
  • Quinazolines / chemical synthesis
  • Quinazolines / chemistry
  • Quinazolines / pharmacology*
  • Quinazolinones / chemical synthesis
  • Quinazolinones / chemistry
  • Quinazolinones / pharmacology*
  • Tetrahydrofolate Dehydrogenase / metabolism

Substances

  • Angiogenesis Inhibitors
  • Anti-Bacterial Agents
  • Anticonvulsants
  • Antineoplastic Agents
  • Enzyme Inhibitors
  • Quinazolines
  • Quinazolinones
  • Tetrahydrofolate Dehydrogenase
  • Phosphotransferases
  • Glucuronidase