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Synthesis and Evaluation of a Series of 3,4,5-Trimethoxycinnamic Acid Derivatives as Potential Antinarcotic Agents
- Title
- Synthesis and Evaluation of a Series of 3,4,5-Trimethoxycinnamic Acid Derivatives as Potential Antinarcotic Agents
- Authors
- Jung J.-C.; Moon S.; Min D.; Park W.K.; Jung M.; Oh S.
- Ewha Authors
- 오세관; 정재철
- SCOPUS Author ID
- 오세관; 정재철
- Issue Date
- 2013
- Journal Title
- Chemical Biology and Drug Design
- ISSN
- 1747-0277
- Citation
- Chemical Biology and Drug Design vol. 81, no. 3, pp. 389 - 398
- Indexed
- SCI; SCIE; SCOPUS
- Document Type
- Article
- Abstract
- A series of 3,4,5-trimethoxycinnamic acid derivatives was prepared and evaluated for antinarcotic effects on morphine dependence in mice and binding affinities on serotonergic receptors. The key synthetic strategies involve generation of ketones 6-7, esters 9-12 through condensation reaction, and amides 13-19 via coupling reaction using 1-hydroxybenzotriazole/ethyl(dimethylaminopropryl)carbodiimide system in high yield. We found that the naloxone-induced morphine withdrawal syndrome was significantly suppressed by new synthetic 3,4,5-trimethoxycinnamic acid derivatives (20mg/kg/day). Most of 3,4,5-trimethoxycinnamic acid derivatives were found to have high affinity to 5-HT1A receptor. The naloxone-induced morphine withdrawal syndrome was attenuated by (+)8-OH-DPAT (0.1mg/kg/day, i.p.), a 5-HT1A receptor agonist. In cortical neuronal cells, (+)8-OH-DPAT (1μm) produced an elevation of the pERK 1/2 expression, and the elevated pERK levels were inhibited by WAY 100635, a 5-HT1A receptor-specific antagonist. Interestingly, the pERK levels were increased by the 3,4,5-trimethoxycinnamic acid derivatives and the derivatives-mediated changes in pERK levels were blocked by the WAY 100635. These results suggested that new synthetic 3,4,5-trimethoxycinnamic acid derivatives have a potential antinarcotic effect through acting as a 5-HT1A receptor agonist in mice. © 2012 John Wiley & Sons A/S.
- DOI
- 10.1111/cbdd.12087
- Appears in Collections:
- 의과대학 > 의학과 > Journal papers
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