Pazinaclone

The issue of Pazinaclone is one of the most relevant issues today, with repercussions in various areas of society. From its origins to its impact on daily life, Pazinaclone has generated passionate debates and has been the subject of numerous studies and research. In this article, we will explore different aspects related to Pazinaclone, analyzing its historical importance, its influence on popular culture and its relevance today. Additionally, we will examine the possible future implications of Pazinaclone and possible solutions to the challenges it poses. Join us on this exciting journey through the world of Pazinaclone!

Pazinaclone
Clinical data
ATC code
  • none
Identifiers
  • 2-(7-chloro-1,8-naphthyridin-2-yl)-3-decan-8-yl)-2-oxoethyl]-3H-isoindol-1-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC25H23ClN4O4
Molar mass478.93 g·mol−1
3D model (JSmol)
  • Clc1nc2nc(ccc2cc1)N4C(=O)c3ccccc3C4CC(=O)N6CCC5(OCCO5)CC6
  • InChI=1S/C25H23ClN4O4/c26-20-7-5-16-6-8-21(28-23(16)27-20)30-19(17-3-1-2-4-18(17)24(30)32)15-22(31)29-11-9-25(10-12-29)33-13-14-34-25/h1-8,19H,9-15H2 checkY
  • Key:DPGKFACWOCLTCA-UHFFFAOYSA-N checkY
  (verify)

Pazinaclone (DN-2327) is a sedative and anxiolytic drug in the cyclopyrrolone family of drugs. Some other cyclopyrrolone drugs include zopiclone and eszopiclone.

Pazinaclone has a very similar pharmacological profile to the benzodiazepines including sedative and anxiolytic properties, but with less amnestic effects, and at low doses it is a relatively selective anxiolytic, with sedative effects only appearing at higher doses.

Pazinaclone produces its sedative and anxiolytic effects by acting as a partial agonist at GABAA benzodiazepine receptors, although pazinaclone is more subtype-selective than most benzodiazepines.

Synthesis

Pazinaclone synthesis: U.S. patent 4,778,801

Reaction of 2-amino-7-chloro-1,8-naphthyridine with phthalic anhydride leads to the corresponding phthalimide. Selective reduction of one of the imide carbonyl groups in essence converts that to an aldehyde. Condensation with tert-butyl(triphenylphosphoranylidene)acetate gives the Wittig product.

The carboxylic acid is then treated with diethyl cyanophosphonate to convert that to an activated acid cyanide; reaction with 1,4-dioxa-8-azaspirodecane results in formation of the corresponding amide, pazinaclone.

See also

References

  1. ^ Wada T, Fukuda N (March 1992). "Effect of a new anxiolytic, DN-2327, on learning and memory in rats". Pharmacology, Biochemistry, and Behavior. 41 (3): 573–9. doi:10.1016/0091-3057(92)90375-p. PMID 1350101. S2CID 20581568.
  2. ^ Suzuki M, Uchiumi M, Murasaki M (October 1995). "A comparative study of the psychological effects of DN-2327, a partial benzodiazepine agonist, and alprazolam". Psychopharmacology. 121 (4): 442–50. doi:10.1007/BF02246492. PMID 8619007. S2CID 35222663.
  3. ^ Atack JR (May 2005). "The benzodiazepine binding site of GABA(A) receptors as a target for the development of novel anxiolytics". Expert Opinion on Investigational Drugs. 14 (5): 601–18. doi:10.1517/13543784.14.5.601. PMID 15926867. S2CID 22793644.
Wikious
Boobota
Sagapedia