1,158
Views
13
CrossRef citations to date
0
Altmetric
Research Article

Pyrazolo[1,5-a]quinazoline scaffold as 5-deaza analogue of pyrazolo[5,1-c][1,2,4]benzotriazine system: synthesis of new derivatives, biological activity on GABAA receptor subtype and molecular dynamic study

, , , , , , , & show all
Pages 195-204 | Received 12 Dec 2014, Accepted 22 Jan 2015, Published online: 20 Mar 2015

References

  • Guerrini G, Ciciani G, Costanzo A, et al. Synthesis of novel cognition enhancer with pyrazolo[5,1-c][1,2,4]benzotriazine core acting at c-aminobutyric acid type A (GABA A) receptor. Bioorg Med Chem 2013;21:2186–98
  • Guerrini G, Ciciani G, Bruni F, et al. Development of ligands at γ-aminobutyrric acid type A (GABAA) receptor subtype as new agents for pain relief. Bioorg Med Chem 2011;19:7441–52
  • Guerrini G, Ciciani G, Bruni F, et al. New 3-,8-disubstituted pyrazolo[5,1-c][1,2,4]benzotriazines useful for studying the interaction with the HBp-3 area (hydrogen bond point area) in the benzodiazepine site on the γ-aminobutyric acid type A (GABAA) receptor. Bioorg Med Chem 2011;19:3074–85
  • Wenthur CJ, Morrison RD, Daniels JS, et al. Synthesis and SAR of substituted pyrazolo[1,5-a]quinazolines as dual mGlu(2)/mGlu(3) NAMs. Bioorg Med Chem Lett 2014;24:2693–8
  • Taliani S, Pugliesi I, Barresi E, et al. Phenylpyrazolo[1,5-a]quinazolin-5(4H)-one: a suitable scaffold for the development of noncamptothecin topoisomerase I (Top1) inhibitors. J Med Chem 2013;56:7458–62
  • Colotta V, Catarzi D, Varano F, et al. Synthesis and binding activity of some pyrazolo[1,5-c]quinazolines as tools to verify an optional binding site of a benzodiazepine receptor ligand. J Med Chem 1996;39:2915–21
  • Catarzi D, Cecchi L, Colotta V, et al. Tricyclic heteroaromatic systems 1,2,4-triazolo[1,5-a]quinaxolines: synthesis and benzodiazepine receptor activity. Farm 1993;48:1065–78
  • Bertelli L. Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors. Eur J Med Chem 2000;35:333–41
  • Nilsson J, Gidlöf R, Nielsen EØ, et al. Triazoloquinazolinediones as novel high affinity ligands for the benzodiazepine site of GABA(A) receptors. Bioorg Med Chem 2011;19:111–21
  • Costanzo A, Guerrini G, Ciciani G, et al. Benzodiazepine receptor ligands. 4: synthesis and pharmacological evaluation of 3-heteroaryl-8-chloropyrazolo[5,1-c][1,2,4]benzotriazine 5-oxides. J Med Chem 1999;42:2218–26
  • Morris GM, Huey R, Lindstrom W, et al. AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem 2009;30:2785–91
  • Jakalian A, Jack DB, Bayly CI. Fast, efficient generation of high-quality atomic charges. AM1-BCC model: II. Parameterization and validation. J Comput Chem 2002;23:1623–41
  • Wang J, Wang W, Kollman PA, Case DA. Automatic atom type and bond type perception in molecular mechanical calculations. J Mol Graph Model 2006;25:247–60
  • Case DA, Darden TA, Cheatham TE III, et al. AMBER 9. San Francisco, CA: University of California; 2006
  • Wang J, Wolf RM, Caldewell JW, et al. Development and testing of a general Amber force field. J Comput Chem 2004;25:56531
  • Jorgensen WL, Chandrasekhar J, Madura JD, et al. Comparison of simple potential functions for simulating liquid water. J Chem Phys 1983;79:926–35
  • Darden T, York D, Pedersen L. Particle mesh Ewald: an N·log(N) method for Ewald sums in large systems. J Chem Phys 1993;98:10089–93
  • Ryckaert JP, Ciccotti G, Berendsen JC. Numerical integration of the Cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes. J Comput Phys 1977;23:327–41
  • Connolly ML. Solvent-accessible surfaces of proteins and nucleic acids. Science 1983;221:709–13
  • Costanzo A, Guerrini G, Bruni F, Selleri S. Reactivity of 1-(2-nitrophenyl)5-aminopyrazoles under basic conditions and synthesis of new 3-,7-, and 8-substituted pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxides, as benzodiazepine receptor ligands. J Heterocycl Chem 1994;31:1369–76
  • Alexander EJ. 4,5-Dihydro-5-oxopyrazolo[1,5-a]quinazoline-3-carboxylic acid derivatives. US1978/4105766 A1; 1978
  • Mayer S, Schann S. Substituted pyrazoloquinazolinones and pyrroloquinazolinones as allosteric modulators of group II metabotropic glutamate receptors. WO 2013/174822 A1; 2013
  • Peet PN. An unexpected aminolysis in the synthesis of 5-substituted 3-(1H-tetrazol-5-yl)pyrazolo[1,5-a]quinazolines. J Heterocycl Chem 1989;26:713–16
  • Penning TD, Thomas SA, Hajduk PJ, et al. Potent PARP inhibitors. US2012/8183250 B2; 2012
  • Lee NK, Lee JW, Lee S, et al. Quinazoline derivatives for the treatment and prevention of diabetes and obesity. 2006 WO2006071095A1. WO2006/071095, 2006
  • Haddach M, La Jolla FP. Tricyclic compounds and pharmaceutical uses thereof. US2001/0065712 A1; 2001
  • Ong CW, Liu M-C, Lee K-D, Chang KW, et al. Synthesis of bisquinoline–pyrrole oligoamide as G-quadruplex binding ligand. Tetrahedron 2012;68:5453–7
  • Catarzi D, Cecchi L, Colotta V, et al. Reaction of 1-aminophtalazines with alpha-halocarbonyl compounds: imidazo[2,1-a]phtalazines and their benzodiazepine receptor activities. Il Farmaco 1993;48:447–57
  • Tarzia G, Occelli E, Toja E, et al. 6-(Alkylamino)-3-aryl-1,2,4-triazolo[3,4-a]phthalazines. A new class of benzodiazepine receptor ligands. J Med Chem 1988;31:1115–23
  • O’Mara M, Cromer B, Parker M, Chung S-H. Homology model of the GABAA receptor examined using Brownian dynamics. Biophys J 2005;88:3286–99

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.