1082730-34-4Relevant articles and documents
General Method for the Preparation of Indole-2-Weinreb Amides
Glas, Carina,Bracher, Franz
, p. 757 - 768 (2019/01/23)
Indole-2-Weinreb amides are obtained via thermolysis of α-azidocinnamic acid Weinreb amides in a Hemetsberger-Knittel-type cyclization. The required vinyl azides are not accessible by Knoevenagel condensation, but are obtained by cerium(IV)-mediated oxida
Synthesis and Evaluation of a Series of 3,4,5-Trimethoxycinnamic Acid Derivatives as Potential Antinarcotic Agents
Jung, Jae-Chul,Moon, Sohyeon,Min, Dongguk,Park, Woo Kyu,Jung, Mankil,Oh, Seikwan
, p. 389 - 398 (2013/04/10)
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.