- Method for synthesizing coumaroyl dopamine by one-pot method
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The invention discloses a method for synthesizing coumaroyl dopamine by one-pot method, which comprises the following steps: (1) reacting coumaric acid serving as a raw material with ethyl chloroformate under the action of triethylamine to obtain an intermediate III; (2) carrying out condensation on the intermediate III and dopamine hydrochloride under the action of triethylamine to obtain an intermediate V; and (3) treating the intermediate V with hydrazine hydrate to obtain a target compound I, namely coumaroyl dopamine. The method has the advantages of high efficiency and high yield, and is suitable for large-scale industrial production.
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Paragraph 0024; 0028; 0029; 0030; 0034; 0035; 0039
(2021/11/19)
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- Synthesis of amide and ester derivatives of cinnamic acid and its analogs: Evaluation of their free radical scavenging and monoamine oxidase and cholinesterase inhibitory activities
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A series of cinnamic acid derivatives, amides (1–12) and esters (13–22), were synthesized, and structure–activity relationships for antioxidant activity, and monoamine oxidases (MAO) A and B, acetylcholinesterase, and butyrylcholinesterase (BChE) inhibitory activities were analyzed. Among the synthesized compounds, compounds 1–10, 12–18, and rosmarinic acid (23), which contained catechol, o-methoxyphenol or 5-hydroxy-indole moieties, showed potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity. Compounds 9–11, 15, 17–22 showed potent and selective MAO-B inhibitory activity. Compound 20 was the most potent inhibitor of MAO-B. Compounds 18 and 21 showed moderate BChE inhibitory activity. In addition, compound 18 showed potent antioxidant activity and MAO-B inhibitory activity. In a comparison of the cinnamic acid amides and esters, the amides exhibited more potent DPPH free radical scavenging activity, while the esters showed stronger inhibitory activities against MAO-B and BChE. These results suggested that cinnamic acid derivatives such as compound 18, p-coumaric acid 3,4-dihydroxyphenethyl ester, and compound 20, p-coumaric acid phenethyl ester, may serve as lead compounds for the development of novel MAO-B inhibitors and candidate lead compounds for the prevention or treatment of Alzheimer’s disease.
- Takao, Koichi,Toda, Kazuhiro,Saito, Takayuki,Sugita, Yoshiaki
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p. 1020 - 1027
(2017/11/17)
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- Preparation method of N-coumaroyldopamine
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The invention discloses a preparation method of N-coumaroyldopamine. The preparation method includes adding 3-hydroxytyramine hydrobromide, methyl p-hydroxycinnamate, and alkaline into a four-port round-bottom flask as well as solvent, stirring, and finishing thin-layer chromatography detection reaction; adding water into reaction solution to separate, adding ethyl acetate for extraction, washing organic phase with saturated salt solution, washing inorganic phase with diluted hydrochloric acid, drying with anhydrous sodium sulfate, filtering, and concentrating to obtain pulp; adding petroleum ether into the pulp, heating to reflow, cooling and standing, pouring solution on the upper layer, adding ethyl acetate into the pulp, mixing, filtering and drying to obtain white solids. Through authentication of nuclear magnetism, the product is N-coumaroyldopamine. In the preparation method of N-coumaroyldopamine, the final product is synthesized directly at one step, synthesis steps are greatly reduced, and production cost is greatly reduced. Moreover, fewer steps facilitate after-treatment of reaction, and purification is simplified.
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Paragraph 0010; 0015-0016
(2017/04/04)
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- Cinnamic acid amides from Tribulus terrestris displaying uncompetitive α-glucosidase inhibition
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The α-glucosidase inhibitory potential of Tribulus terrestris extracts has been reported but as yet the active ingredients are unknown. This study attempted to isolate the responsible metabolites and elucidate their inhibition mechanism of α-glucosidase. By fractionating T. terristris extracts, three cinnamic acid amide derivatives (1-3) were ascertained to be active components against α-glucosidase. The lead structure, N-trans-coumaroyltyramine 1, showed significant inhibition of α-glucosidase (IC50 Combining double low line 0.42 μM). Moreover, all active compounds displayed uncompetitive inhibition mechanisms that have rarely been reported for α-glucosidase inhibitors. This kinetic behavior was fully demonstrated by showing a decrease of both Km and Vmax, and Kik/Kiv ratio ranging between 1.029 and 1.053. We progressed to study how chemical modifications to the lead structure 1 may impact inhibition. An α, β-unsaturation carbonyl group and hydroxyl group in A-ring of cinnamic acid amide emerged to be critical functionalities for α-glucosidase inhibition. The molecular modeling study revealed that the inhibitory activities are tightly related to π-π interaction as well as hydrogen bond interaction between enzyme and inhibitors.
- Song, Yeong Hun,Kim, Dae Wook,Curtis-Long, Marcus J.,Park, Chanin,Son, Minky,Kim, Jeong Yoon,Yuk, Heung Joo,Lee, Keun Woo,Park, Ki Hun
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p. 201 - 208
(2016/05/02)
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- Synthesis of phenolic amides and evaluation of their antioxidant and anti-inflammatory activity in vitro and in vivo
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A series of 15 phenolic amides (PAs) have been synthesized (PA1-PA15) and examined in vitro by four different tests: (1) prevention of Cu2+-induced human low-density lipoprotein oxidation, (2) scavenging of stable radicals, (3) anti-inflammatory activity, (4) scavenging of superoxide radicals. We used PA1 and α-tocopherol for an in vivo study. The overall potential of the antioxidant system was significantly enhanced by the PA1 and α-tocopherol supplements as the hepatic TBARS levels were lowered while the hepatic SOD activities and GSH concentration were elevated in PA1 fed rats. Our results support that PA1 may exert antioxidant action through inhibiting superoxide generation. PA1 decreased the level of nitric oxide (NO) production, tumor necrosis factor-alpha (TNF-α) and nuclear factor-kappa B (NF-κB). These results show that PA1 can inhibit lipid peroxidation, enhance the activities of antioxidant enzymes, and decrease the TNF-α/NF-κB level and nitric oxide production. Therefore, it was speculated that PA1 acts through its anti-inflammation capacity.
- Lee, Ya-Ting,Hsieh, You-Liang,Yeh, Yen-Hung,Huang, Chih-Yang
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p. 85806 - 85815
(2015/11/03)
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- Anti-tyrosinase, antioxidant and antimicrobial activities of hydroxycinnamoylamides
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Synthetic hydroxycinnamoylamides of amino acids (precursors of aromatic amines) were studied for their antioxidant activity in vitro by two antioxidant assay systems, including 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and inhibition of lipid peroxidation (LPO). Furthermore, these compounds were tested and compared with their corresponding cinnamoylamides of aromatic amines for their inhibitory activity using mushroom tyrosinase. In addition, five hydroxycinnamoyl amino acid amides were investigated for their antimicrobial effect. Structure-activity relationships analysis disclosed that the presence of catechol rest at amino acid or at benzene moieties of substituted cinnamic acid amides significantly scavenged DPPH radical and inhibited LPO. The results obtained by LPO clearly expressed the positive influence of indole moiety on the activity. Moreover, the existence of p-hydroxy substituted cinnamic acid moiety leads to better tyrosinase inhibition. Amongst the tested compounds, amides of p-coumaroyldopamine or tyramine and their corresponding amino acid precursors are the most potent tyrosinase inhibitors.
- Georgiev, Lyubomir,Chochkova, Maya,Totseva, Iskra,Seizova, Katya,Marinova, Emma,Ivanova, Galya,Ninova, Mariana,Najdenski, Hristo,Milkova, Tsenka
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p. 4173 - 4182
(2013/09/02)
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- Synthesis and structure-activity relationships and effects of phenylpropanoid amides of octopamine and dopamine on tyrosinase inhibition and antioxidation
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Phenylpropanoid amides of octopamine (OA) 1a-1e and dopamine (DA) 2a-2e were synthesised and the structure-activity relationships (SARs) for antioxidant and tyrosinase inhibition activities were analysed. Among synthesised compounds, 2c, which contains two catechol moieties, exhibited the most DPPH radical-scavenging activity (EC50 = 16.2 ± 2.4 μM), and 1d exhibited significant tyrosinase inhibitory activity (IC50 = 5.3 ± 1.8 μM). Interestingly, with the same acid moiety, OA derivatives showed more inhibitory effect on tyrosinase than did compounds derived from DA, whereas DA derivatives were found to have higher antioxidant activity than compounds derived from OA. The relationship between their structures and their potencies, demonstrated in the current study, will be useful for the design of optimal agents.
- Wu, Zhengrong,Zheng, Lifang,Li, Yang,Su, Feng,Yue, Xiaoxuan,Tang, Wei,Ma, Xiaoyan,Nie, Junyu,Li, Hongyu
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p. 1128 - 1131
(2012/07/28)
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- Inhibition of in vitro prostaglandin and leukotriene biosyntheses by cinnamoyl-β-phenethylamine and N-acyldopamine derivatives
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N-trans- and N-cis-Feruloyltyramines were isolated as the inhibitors of in vitro prostaglandin (PG) synthesis from an Indonesian medicinal plant, Ipomoea aquatica (Convolvulaceae). In order to clarify structure activity relationships, cinnamoyl-β-phenethylamines with possible combinations of naturally occurring cinnamic acids and β-phenethylamines were synthesized and tested for their inhibitory activities against PG synthetase and arachidonate 5-lipoxygenase. The compounds containing catechol groups such as N-caffeoyl-β-phenethylamine (CaP) showed higher inhibitory effects on PG synthetase. The catechol group was found to M essential for the inhibition of arachidonate 5-lipoxygenase. The investigation of concentration dependent effects on PG biosynthesis revealed that CaP enhanced PG biosynthesis at a lower concentration range, whereas it inhibited the reaction at a higher concentration. The effects of CaP on each reaction step were investigated with purified PG endoperoxide synthase and microsomal PG synthetase. CaP inhibited the cyclooxygenase reaction, while it enhanced the hydroperoxidase reaction. N-Acyldopamines which contain catechol and lipophylic group were synthesized from dopamine and fatty acids to test their inhibitory effects on arachidonate 5-lipoxygenase. N-Linoleoyldopamine was the most active compound and its IC50 value was 2.3 nM in our assay system, in which an IC50 value of AA 861, a specific inhibitor of 5-lipoxygenase, was 8 nM.
- Tseng,Iwakami,Mikajiri,Shibuya,Hanaoka,Ebizuka,Padmawinata,Sankawa
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p. 396 - 400
(2007/10/02)
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