Synthesis and biological evaluation of 3,7-diazabicyclo[4.3.0]nonan-8-ones as potential nootropic and analgesic drugs.

Abstract

A series of cis and trans 3,7-diazabicyclo[4.3.0]nonan-8-ones has been synthesized and tested for their ability to revert scopolamine-induced amnesia in the mouse passive-avoidance test. The racemates of the most potent compounds 4 and 7 were separated and tested, but no enantioselectivity was found for the nootropic activity. Compounds 4 and 7 and their enantiomers displayed interesting antihyperalgesic activity in two models of neuropathic pain (streptozotocin-induced and oxalilplatin-induced neuropathy) in comparison with pregabalin.

• Authors: Elisabetta Martini, Lorenzo Di Cesare Mannelli, Gianluca Bartolucci, Carlo Bertucci, Silvia Dei, Carla Ghelardini, Luca Guandalini, Dina Manetti, Serena Scapecchi, Elisabetta Teodori, Maria Novella Romanelli
• Journal: Journal of medicinal chemistry (J Med Chem) Vol. 54 Issue 7 Pg. 2512-6 (Apr 14 2011) ISSN: 1520-4804 [Electronic] United States
• PMID: 21381762 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Analgesics
• Ketones
• Nootropic Agents
• Scopolamine

Topics

• Amnesia (chemically induced, drug therapy)
• Analgesics (chemical synthesis, chemistry, pharmacology, therapeutic use)
• Animals
• Behavior, Animal (drug effects)
• Drug Design
• Ketones (chemical synthesis, chemistry, pharmacology, therapeutic use)
• Mice
• Nootropic Agents (chemical synthesis, chemistry, pharmacology, therapeutic use)
• Scopolamine (pharmacology)
• Stereoisomerism