Synthesis of substituted cinnamoyl-tyramine derivatives and their platelet anti-aggregatory activities

Woo, Nam-Tae; Jin, Sun; Cho, Dae Jin; Kim, Nam Sun; Bae, Eun Hyung; Han, Ducky; Han, Byung Hoon; Kang, Young‐Hwa

doi:10.1007/bf02974047

Cited by 4 publications

(2 citation statements)

References 6 publications

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“…Compound 3 and 11 had an antihyperglycemic effect as inhibition percentage of 20.1% and 30.7% in sucrose-loaded model (SLM) at a dosage of 100 mg/kg-body weight [ 16 , 17 ]. Compound 5 inhibited platelet aggregation with the IC 50 value of 2.6 μM [ 18 ]. Compound 10 and 11 showed anti-inflammatory activity with 50% NO inhibition concentration as 14.08 μM and 15.08 μM, respectively [ 19 , 20 ].…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis of N-phenethyl Cinnamide Derivatives and Their Biological Activities for the Treatment of Alzheimer’s Disease: Antioxidant, Beta-amyloid Disaggregating and Rescue Effects on Memory Loss

et al. 2018

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Gx-50 is a bioactive compound for the treatment of Alzheimer’s disease (AD) found in Sichuan pepper (Zanthoxylum bungeanum). In order to find a stronger anti-AD lead compound, 20 gx-50 (1–20) analogs have been designed and synthesized, and their molecular structures were determined based on nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis, as well as comparison with literature data. Compounds 1–20 were evaluated for their anti-AD potential by using DPPH radical scavenging assay for considering their anti-oxidant activity, thioflavin T (ThT) fluorescence assay for considering the inhibitory or disaggregate potency of Aβ, and transgenic Drosophila model assay for evaluating their rescue effect on memory loss. Finally, compound 13 was determined as a promising anti-AD candidate.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis of N-phenethyl Cinnamide Derivatives and Their Biological Activities for the Treatment of Alzheimer’s Disease: Antioxidant, Beta-amyloid Disaggregating and Rescue Effects on Memory Loss

et al. 2018

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“…TMCA amides have been revealed to show hematologic activity, in which anti-aggregatory and haemostatic effect are the relative effects.Substituted cinnamoyl-tyramine analogues were synthesized and evaluated the platelet anti-aggregatory activity [79]. Among the synthetic derivatives, amides S68 and S69 (Fig.…”

Section: Hematologic Activity Of Synthetic Tmca Derivativesmentioning

confidence: 99%

Research progress in the biological activities of 3,4,5-trimethoxycinnamic acid (TMCA) derivatives

Zhao

Song

Xie

et al. 2019

European Journal of Medicinal Chemistry

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a b s t r a c t TMCA (3,4,5-trimethoxycinnamic acid) ester and amide are privileged structural scaffolds in drug discovery which are widely distributed in natural products and consequently produced diverse therapeutically relevant pharmacological functions. Owing to the potential of TMCA ester and amide analogues as therapeutic agents, researches on chemical syntheses and modifications have been carried out to druglike candidates with broad range of medicinal properties such as antitumor, antiviral, CNS (central nervous system) agents, antimicrobial, anti-inflammatory and hematologic agents for a long time. At the same time, SAR (structure-activity relationship) studies have draw greater attention among medicinal chemists, and many of the lead compounds were derived for various disease targets. However, there is an urgent need for the medicinal chemists to further exploit the precursor in developing chemical entities with promising bioactivity and druggability. This review concisely summarizes the synthesis and biological activity for TMCA ester and amide analogues. It also comprehensively reveals the relationship of significant biological activities along with SAR studies.

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Characterization and profiling of phenolic amides from Cortex Lycii by ultra-high performance liquid chromatography coupled with LTQ-Orbitrap mass spectrometry

et al. 2014

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Cortex Lycii, the root bark of Lycium chinense Mill. or Lycium barbarum L., is a frequently used traditional Chinese medicine. Phytochemical studies have shown that phenolic amides are not only characteristic compounds but also abundant ones in this plant. In the present study, an effective method was developed for structural characterization of phenolic amides from Cortex Lycii by ultra-high performance liquid chromatography coupled with linear ion trap Orbitrap tandem mass spectrometry. The fragmentation of 14 compounds including six cinnamic acid amides, six neolignanamides, and two lignanamides were studied systematically for the first time. It was found that, in the positive ion mode, neutral loss of the tyramide moiety (137 Da) or N-(4-aminobutyl)acetamide moiety (130 Da) were characteristic for these compounds. At least 54 phenolic amides were detected in the extract and 48 of them were characterized, among which 14 known compounds were identified unambiguously by comparing the retention time and mass spectra with those of reference compounds, and 34 components were tentatively identified based on the fragmentation patterns, exact mass, UV spectra, as well as retention time. Fifteen compounds were characterized as potential new ones. Additionally, the developed method was applied to analyze eight batches of samples collected from the northwest of China, and it was found that cinnamic acid amides were the main type of phenolic amides in Cortex Lycii. In conclusion, the identification of these chemicals provided essential data for further phytochemical studies, metabolites identification, and the quality control of Cortex Lycii.

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Synthesis of substituted cinnamoyl-tyramine derivatives and their platelet anti-aggregatory activities

Cited by 4 publications

References 6 publications

Design, Synthesis of N-phenethyl Cinnamide Derivatives and Their Biological Activities for the Treatment of Alzheimer’s Disease: Antioxidant, Beta-amyloid Disaggregating and Rescue Effects on Memory Loss

Design, Synthesis of N-phenethyl Cinnamide Derivatives and Their Biological Activities for the Treatment of Alzheimer’s Disease: Antioxidant, Beta-amyloid Disaggregating and Rescue Effects on Memory Loss

Research progress in the biological activities of 3,4,5-trimethoxycinnamic acid (TMCA) derivatives

Characterization and profiling of phenolic amides from Cortex Lycii by ultra-high performance liquid chromatography coupled with LTQ-Orbitrap mass spectrometry

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