22214-30-8Relevant articles and documents
Competitive influence of carboxylic groups in ionic complex formation of 4-hydroxybenzylidene alkanones with polyamidines
Dudkina, Marina M.,Tenkovtsev, Andrey V.,Komber, Hartmut,Haeussier, Liane,Boehme, Frank
, p. 8389 - 8393 (2004)
Interactions of phenolic and carboxylic group containing chromophores (hydroxyarylidene alkanones) with polyamidines were investigated by UV/vis and 1H NMR spectroscopy. Because of the strong basicity of the polyamidines, deprotonation of the c
Isolation of E-1-(4'-hydroxyphenyl)-but-1-en-3-one from Scutellaria barbata
Ducki,Hadfield,Lawrence,Liu,McGown,Zhang
, p. 185 - 186 (1996)
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Synthesis and antiviral activities of novel penta-1,4-diene-3-one oxime derivatives bearing a pyridine moiety
Wang, Xiaobin,Chen, Meihang,Li, Qin,Zhang, Juping,Ruan, Xianghui,Xie, Yan,Xue, Wei
, p. 1225 - 1233 (2017)
A series of novel penta-1,4-diene-3-one oxime ether derivatives bearing a pyridine moiety were designed and synthesized, and their antiviral activities against tobacco mosaic virus (TMV) were evaluated. The results of the biological assay indicated that most of the title compounds exhibit good antiviral activities against TMV at 500 μg/mL. In particular, the title compounds 5c, 5j, 5o and 5p showed remarkable curative activities against TMV, with EC50 values of 274.8, 299.2, 251.8 and 287.7 μg/mL, respectively, which were superior to that of ribavirin (379.8 μg/mL). This study indicates that penta-1,4-diene-3-one oxime ether derivatives bearing a pyridine moiety can serve as potential alternative templates in the search for novel, highly efficient, anti-plant viral agents.
Preparation of a raspberry ketone precursor in the presence of rare earth oxide catalysts
Hoelderich, Wolfgang F.,Ritzerfeld, Verena
, p. 654 - 663 (2015)
The raspberry precursor 4-(4-hydroxyphenyl)-but-3-ene-2-one which afterwards undergoes a catalytic hydrogenation to produce raspberry ketone was synthesized by aldol condensation of acetone and 4-hydroxybenzaldehyde over rare earth oxides as basic catalysts and supported rare earth oxides as acid-base bifunctional catalysts. Thereby, several rare earth metal oxides were tested in their neat form as well as supported on carriers with high surface areas such as alumina, titania, tetragonal zirconia and charcoal. The catalysts were characterized by XRD, BET, NH3/CO2-TPD and pyridine-FTIR. All experiments were carried out batch wise in 75 ml autoclaves adjusting molar ratios of acetone and 4-hydroxybenz-aldehyde from 12:1 to 4:1, temperature range from 80 to 200 °C and autogeneous pressures from 1 to 25 bar. It could also be realized, that titania and alumina are no inert materials, but also highly active catalysts for this reaction. An experimental design program was used to optimize the reaction conditions as well as the conversion and selectivity. In addition the reaction was carried out in a fixed bed plug flow reactor to determine stability and robustness of the catalyst. The quality/contaminations of the starting material have a strong influence on the catalytic performance.
Antimicrobial evaluation and action mechanism of pyridinium-decorated 1,4-pentadien-3-one derivatives
Zhou, Jian,Tao, Qing-Qing,Wang, Pei-Yi,Shao, Wu-Bin,Wu, Zhi-Bing,Li, Zhong,Yang, Song
, p. 1742 - 1746 (2018)
A type of pyridinium-decorated 1,4-pentadien-3-one derivatives possessing flexible alkyls were designed and synthesized by integrating the key scaffolds of pyridinium cations and 1,4-pentadien-3-one skeleton in a single molecular architecture. Antimicrobial bioassays indicated that some of the target molecules exerted considerable bioactivities against six phytopathogenic strains, especially for Xanthomonas oryzae pv. oryzae, the minimal EC50 value can reach to 0.504 μg/mL. A plausible action mechanism for this kind of compounds was proposed and confirmed by employing fluorescent spectroscopy, fluorescence microscopy, and scanning electron microscopy. We anticipated that this finding can promote high-efficient lead compounds discovery in the research of antimicrobial chemotherapy.
An efficient Pd@Pro-GO heterogeneous catalyst for the α, β-dehydrogenation of saturated aldehyde and ketones
Pan, Gao-Fei,Wang, Zhe,Chang, Yi-Yuan,Hao, Yue,Wang, Yi-Chen,Xing, Rui-Guang
supporting information, (2021/12/30)
An Efficient Pd@Pro-GO heterogeneous catalyst was developed that can promote the α, β-dehydrogenation of saturated aldehyde and ketones in the yield of 73% ? 92% at mild conditions without extra oxidants and additives. Pd@Pro-GO heterogeneous catalyst was synthesized via two steps: firstly, the Pro-GO was obtained by the esterification reaction between graphene oxide (GO) and N-(tert-Butoxycarbonyl)-L-proline (Boc-Pro-OH), followed by removing the protection group tert-Butoxycarbonyl (Boc), which endowed the proline-functionalized GO with both the lewis acid site (COOH) and the bronsted base site (NH), besides, the pyrrolidine of proline also can form imine with aldehydes to activate these substrates; Second, palladium was dispersed on the proline-functionalized GO (Pro-GO) to obtained heterogeneous catalyst Pd@Pro-GO. Mechanistic studies have shown that the Pd@Pro-GO-catalyzed α,β-dehydrogenation of saturated aldehyde and ketones was realized by an improved heterogeneously catalyzed Saegusa oxidation reaction. Based on the obove characteristics, the Pd@Pro-GO will be widely used in the transition metal catalytic field.
Design, green synthesis, antioxidant activity screening, and evaluation of protective effect on cerebral ischemia reperfusion injury of novel monoenone monocarbonyl curcumin analogs
He, Wenfei,Wang, Jingsong,Jin, Qiling,Zhang, Jiafeng,Liu, Yugang,Jin, Zewu,Wang, Hua,Hu, Linya,Zhu, Lu,Shen, Mengya,Huang, Lili,Huang, Shengwei,Li, Wulan,Zhuge, Qichuan,Wu, Jianzhang
, (2021/07/06)
Antioxidants with high efficacy and low toxicity have the potential to treat cerebral ischemia reperfusion injury (CIRI). Dienone monocarbonyl curcumin analogs (DMCA) capable of overcoming the instability and pharmacokinetic defects of curcumin possess notable antioxidant activity but are found to be significantly toxic. In this study, a novel skeleton of the monoenone monocarbonyl curcumin analogue sAc possessing reduced toxicity and improved stability was designed on the basis of the DMCA skeleton. Moreover, 32 sAc analogs were obtained by applying a green, simple, and economical synthetic method. Multiple sAc analogs with an antioxidant protective effect in PC12 cells were screened using an H2O2-induced oxidative stress damage model, and quantitative evaluation of structure–activity relationship (QSAR) model with regression coefficient of R2 = 0.918921 was built through random forest algorithm (RF). Among these compounds, the optimally active compound sAc15 elicited a potent protective effect on cell growth of PC12 cells by effectively eliminating ROS generation in response to oxidative stress injury by activating the Nrf2/HO-1 antioxidant signaling pathway. In addition, sAc15 exhibited good protection against CIRI in the mice middle cerebral artery occlusion (MCAO) model. In this paper, we provide a novel class of antioxidants and a potential compound for stroke treatment.
8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study
Xing, Gang,Zhi, Zhengxing,Yi, Ce,Zou, Jitian,Jing, Xuefeng,Yiu-Ho Woo, Anthony,Lin, Bin,Pan, Li,Zhang, Yuyang,Cheng, Maosheng
, (2021/07/19)
β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.
