Resolution and chiral recognition of muscone as well as actions on neural system.

Abstract

In this letter, (R)-muscone and (S)-muscone were prepared by optical resolution of dl-muscone using N,N'-dibenzyl-l-tartaramide or N,N'-dibenzyl-d-tartaramide, according to the method reported by Kunihiko Takabe. But we separated the diastereomers using EtOH instead of MeOH in the recrystallization step to get the goal product with higher optical purity and yield. The regulatory effect of muscone and its enantiomer on the neural system showed that they could prolong mouse hypoxia tolerance and dose-dependently enhance mouse spinal cord stimulation induced by strychnine nitrate. (R)-muscone and (S)-muscone had a synergistic action on shortening sleep time induced by sodium pentobarbital in mice.

• Authors: Yu Meng, Qiong Xiao, Jin-Ye Bai, Xuan Xiao, Shu Zhang, Xiu-Yuan Zhu, Gui-Fang Cheng, Da-Li Yin
• Journal: Journal of Asian natural products research (J Asian Nat Prod Res) Vol. 16 Issue 12 Pg. 1166-70 (Dec 2014) ISSN: 1477-2213 [Electronic] England
• PMID: 25559500 (Publication Type: Journal Article)

Chemical References

• Cycloparaffins
• Strychnine
• muscone
• Phenobarbital

Topics

• Animals
• Cycloparaffins (chemistry, pharmacology)
• Dose-Response Relationship, Drug
• Hippocampus (physiology)
• Hypoxia (metabolism)
• Mice
• Molecular Structure
• Nervous System (drug effects)
• Neurons (physiology)
• Phenobarbital (pharmacology)
• Stereoisomerism
• Strychnine (pharmacology)