- The fluorescence properties of 4′-Methoxychalcone derivates modified by substituents and investigation of lysosomal imaging
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Three types of 4′-methoxychalcone derivatives Cha-1 ~ Cha-9 with different electron-withdrawing or electron-donating substituents at different positions were synthesized and studied. When the A ring has a hydroxyl group at the 2-position, the strong electron-donating groups at the 4-position of the B ring was more conducive to the near-infrared and aggregation-enhanced emission (AEE) features of the compound than the electron withdrawing groups. The single-crystal analysis confirmed that the good planarity of the 4′-methoxychalcone derivatives favors their fluorescence quantum yields. Moreover, chalcone fluorophores with different fluorescence properties could be obtained by modulating substituent at the 2-position of A ring. In addition, Cha-9 was selected as the AEE luminogen to locate the lysosomes in HeLa cells. These results provided fundamental knowledge for the design and application of 4′-methoxychalcone derivatives of aggregation-induced emission (AIE) compounds.
- Cai, Zhengxu,Dong, Yuping,Lin, Na,Shi, Jianbing,Tong, Bin,Wu, Xinghui
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- Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles
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Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).
- Chang, Weixing,Kong, Jingyang,Li, Jing,Liu, Lingyan,Wang, Hongkai,Zeng, Tianlong
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supporting information
p. 4024 - 4032
(2021/07/12)
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- Ultrasound assisted synthesis and cytotoxicity evaluation of known 2′,4′-dihydroxychalcone derivatives against cancer cell lines
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This work reports on the development of an efficient and ecofriendly ultrasound assisted method for the high yield synthesis (70.0–94.0%) of eighteen oxyalkylated derivatives of 2′,4′-dihydroxychalcone. Synthesized compounds were subjected to in vitro biological assays against HT-29 (colorectal), MCF-7 (breast), and PC-3 (prostate) human tumor cell lines, these cell lines are among the ten most aggressive malignancies diagnosed in the world. Cytotoxicity evaluations showed that four of the synthesized compounds exhibited moderate to very high toxic activity against MCF-7 (IC50 = 8.4–34.3 μM) and PC-3 (IC50 = 9.3–29.4 μM) – comparable to 5-fluorouracil (IC50 16.4–22.3 μM). The same compounds only showed moderate activity against HT-29 (IC50 15.3–36.3 μM), closer to daunorubicin (IC50 15.1 μM). Next, although selectivity index (SI) of compounds was weak, compound 18 exhibited a remarkable and selective cytotoxic activity (5.8–10.57) against cancer cells. Outside of these, most compounds significantly reduced cell survival, increased reactive oxygen species (ROS) and caspase activity, and decreased mitochondrial membrane permeability. In this sense, a portion of anti-proliferative activity is due to apoptosis. Notwithstanding, due to its remarkable response, chalcone 18 may be a potential alternative as a chemotherapeutic anti-carcinogen.
- Villena, Joan,Montenegro, Iván,Said, Bastian,Werner, Enrique,Flores, Susana,Madrid, Alejandro
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- A novel one-pot synthesis of flavones
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In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.
- Chang, Meng-Yang,Tsai, Min-Chen,Lin, Chun-Yi
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p. 11655 - 11662
(2021/03/31)
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- Hydroxychalcone dyes that serve as color indicators for pH and fluoride ions
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A chalcone, which is composed of two aromatic rings bridged by an α,β-unsaturated carbonyl group, exhibits a variety of biological activities. With an objective to develop a novel chalcone-based functional dye, we have synthesized a chalcone diol CLN1, bearing two OH groups at the 2-positions on both phenyl rings, as well as reference compounds CLN2-6, and found that it serves as color indicators for pH and fluoride ions. CLN1showed a vivid color change from colorless to yellow (halochromism) in water at pH ≥ 10. Furthermore, it presented a selective color change from colorless to red upon the addition of TBAF in an organic solvent such as CH3CN. CLN1provided a strong red-shifted absorption band in the visible region under alkaline conditions in water and upon the addition of TBAF in CH3CN. The absorption spectral study together with TD-DFT calculations and X-ray crystallographic analysis revealed that the characteristic π-resonant structures of CLN1caused by the ionization or OH-F?interactions and the planar conformation due to its intramolecular hydrogen bonding may provide a strong charge transfer (CT) absorption in the visible region.
- Bu, Ren,Du, Yanqing,Eerdun, Chaolu,Hu, Mixia,Liang, Fengying,Tsuda, Akihiko,Wang, Meiling
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p. 37463 - 37472
(2020/10/28)
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- Flavanone-based fluorophores with aggregation-induced emission enhancement characteristics for mitochondria-imaging and zebrafish-imaging
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Fluorophores with aggregation-induced emission enhancement (AIEE) characteristics applied in bioimaging have attracted more and more attention in recent years. In this work, a series of flavanone compounds with AIEE characteristics was developed and applied to fluorescence imaging of mitochondria and zebrafish. The compounds were readily prepared by the thermal dehydration of chalcone that was obtained by the reaction of o-hydroxyacetophenone and benzaldehyde. Two of these compounds showed significant AIEE characteristics by fluorescence performance experiments, including optical spectra, fluorescence spectra, fluorescence quantum yield (?F), fluorescence lifetime, and scanning electron microscopy (SEM). Compared with traditional organic fluorescent dyes, these compounds have high fluorescence emission and high fluorescence quantum yield in solid or aggregated state, which overcomes the shortcoming of aggregation-caused quenching (ACQ). More importantly, the two compounds exhibited low cytotoxicity and good cytocompatibility in A549 lung cells at the experimental concentration range and they specifically targeted mitochondria, which make it of great potential use in mitochondria labeling. In addition, they were embryonic membrane permeable and had different affinities for different tissues and organs of zebrafish, but mainly distributed in the digestive system, providing a basis for the application of such compounds in bioimaging. These AIEE compounds with superior properties could be of great potential use in mitochondria imaging and other in vivo studies.
- He, Feng,Li, Na,Liu, Liyan,Luo, Huiqing,Wang, Huaqiao,Yang, Depo
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- Chiral Hydroxytetraphenylene-Boron Complex Catalyzed Asymmetric Diels-Alder Cycloaddition of 2′-Hydroxychalcones
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(S)-2,15-Cl2-DHTP-boron complex catalyst for the asymmetric Diels-Alder cycloaddition of 2′-hydroxychalcones and dienes was developed and tested. The resulting cyclohexenes with three chiral centers were obtained in high yields (up to 98%) with excellent stereoselectivities (up to >20:1 endo/exo, >99% ee). This catalytic system features high efficiency, broad substrate scopes, and mild reaction conditions. In addition, a DFT study was performed to explain the stereochemical course of the asymmetric induction.
- Chai, Guo-Li,Qiao, Yan,Zhang, Ping,Guo, Rong,Wang, Juan,Chang, Junbiao
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supporting information
p. 8023 - 8027
(2020/11/02)
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- Design, synthesis and QSAR study of 2′-hydroxy-4′-alkoxy chalcone derivatives that exert cytotoxic activity by the mitochondrial apoptotic pathway
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Eleven 4′-alkoxy chalcones were synthesized and biologically evaluated for their antiproliferative activity against four human tumor cell lines (PC-3, MCF-7, HF-6, and CaSki). Compounds 3a-3d and 3f were selective against PC-3, with IC50 values ranging from 8.08 to 13.75 μM. In addition, chalcones 3a-3c did not affect the normal fibroblasts BJ cells. The most active and selective compounds were further evaluated for their effect on the progression of cell cycle in PC-3 cells, and chalcones 3a and 3c induced a G2/M phase arrest. Furthermore, it was found that these three chalcones induced the mitochondrial apoptotic pathway by regulating Bax and Bcl-2 transcripts and by increasing caspase 3/7 activation. Otherwise, the QSAR model indicates that the double bond of the α,β-unsaturated carbonyl, as well as the planar structure geometry, are important to the biological activity of the synthetized chalcones. Based on these studies, it was concluded that withdrawing substituents in ring A, decrease the antiproliferative activity. This is related to the possible mechanism of action of these compounds, where a Michael addition needs to take place in order to be a potent anticancer agent.
- Marquina, Silvia,Maldonado-Santiago, Maritza,Sánchez-Carranza, Jessica Nayelli,Antúnez-Mojica, Mayra,González-Maya, Leticia,Razo-Hernández, Rodrigo Said,Alvarez, Laura
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- From Carbamate to Chalcone: Consecutive Anionic Fries Rearrangement, Anionic Si → C Alkyl Rearrangement, and Claisen-Schmidt Condensation
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A highly efficient one-pot procedure was developed for the synthesis of various 2′-hydroxychalcones from phenyl diethylcarbamate, featuring consecutive Snieckus-Fries rearrangement, anionic Si a?' C alkyl rearrangement, and Claisen-Schmidt condensation in a single operation. The applicability of this protocol was demonstrated by the highly efficient synthesis of the anti-inflammatory natural product lonchocarpin. The mechanism insight is also provided.
- Kumar, Singam Naveen,Bavikar, Suhas Ravindra,Pavan Kumar, Chebolu Naga Sesha Sai,Yu, Isaac Furay,Chein, Rong-Jie
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supporting information
p. 5362 - 5366
(2018/09/12)
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- Chalcone derivatives enhance ATP-binding cassette transporters A1 in human THP-1 macrophages
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Atherosclerosis is a process of imbalanced lipid metabolism in the vascular walls. The underlying pathology mainly involves the deposition of oxidized lipids in the endothelium and the accumulation of cholesterol in macrophages. Macrophages export excessive cholesterol (cholesterol efflux) through ATP-binding cassette transporter A1 (ABCA1) to counter the progression of atherosclerosis. We synthesized novel chalcone derivatives and assessed their effects and the underlying mechanisms on ABCA1 expression in macrophages. Human THP-1 macrophages were treated with synthetic chalcone derivatives for 24 h. In Western blot and flow cytometry analyses, a chalcone derivative, (E)-1-(3,4-diisopropoxyphenyl)-3-(4-isopropoxy-3-methoxyphenyl)prop- 2-en-1-one (1m), was observed to significantly enhance ABCA1 protein expression in THP-1 cells (10 μM, 24 h). Levels of mRNA of ABCA1 and liver X receptor alpha (LXRα) were quantified using a real-time quantitative polymerase chain reaction technique and were found to be significantly increased after treatment with the novel chalcone derivative 1m. Several microRNAs, including miR155, miR758, miR10b, miR145, miR33, and miR106b, which functionally inhibit ABCA1 expression were suppressed after treatment with 1m. Collectively, 1m increases ABCA1 expression in human THP-1 macrophages. The mechanisms involve the activation of the LXRα-ABCA1 pathway and suppression of certain microRNAs that regulate ABCA1 expression.
- Teng, I-Jou,Tsai, Min-Chien,Shih, Shao-Fu,Tsuei, Bi-Feng,Chang, Hsin,Chuang, Yi-Ping,Lin, Chin-Sheng,Chern, Ching-Yuh,Chen, Sy-Jou
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- In Vitro and in Vivo Antischistosomal Activities of Chalcones
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In this study, we evaluated the in vitro and in vivo schistosomicidal activities of chalcones against Schistosoma mansoni worms. In vitro assays revealed that chalcones 1 and 3 were the most active compounds, without affecting significantly mammalian cells. Confocal laser scanning microscopy and scanning electron microscopy studies revealed reduction on the numbers of tubercles and morphological alterations in the tegument of S. mansoni worms after in vitro incubation with chalcones 1 and 3. In a mouse model of schistosomiasis, the oral treatment (400 mg/kg) with chalcone 1 or 3 significantly caused a total worm burden reduction in mice. Chalcone 1 showed significant inhibition of the S. mansoni ATP diphosphohydrolase activity, which was corroborated by molecular docking studies. The results suggested that chalcones could be explored as lead compounds with antischistosomal properties.
- Pereira, Vinícius R. D.,Junior, Ismael J. Alves,da Silveira, Lígia S.,Geraldo, Reinaldo B.,de F. Pinto, Priscila,Teixeira, Fernanda S.,Salvadori, Maria C.,Silva, Marcos P.,Alves, Lara A.,Capriles, Priscila V. S. Z.,das C. Almeida, Ayla,Coimbra, Elaine S.,Pinto, Pedro L. S.,Couri, Mara R. C.,de Moraes, Josué,Da Silva Filho, Ademar A.
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- NOTCH INHIBITORS FOR USE IN THE TREATMENT OF T-CELL ACUTE LYMPHOBLASTIC LEUKEMIA
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Compounds of formula (I) in the capacity of compounds with anti-tumor activity for the treatment of T-cell acute lymphoblastic leukemia (T-ALL).
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Page/Page column 25; 32-33
(2018/07/29)
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- Synthesis of 5-subsituted flavonols via the Algar-Flynn-Oyamada (AFO) reaction: The mechanistic implication
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Herein, we report a synthetic method with improved selectivity for 5-substituted flavonols via the Algar-Flynn-Oyamada reaction (AFO), by using of sodium carbonate/hydrogen peroxide A series of 5-substituted flavonols was obtained with moderate to high yields. The mechanism of the AFO reaction was elucidated. LCMS analysis and in situ 1H NMR analysis indicated that the epoxide was involved in the transformation from chalcone to flavonol and/or aurone under alkaline base/peroxide conditions.
- Shen, Xianyan,Zhou, Qiang,Xiong, Wei,Pu, Wenchen,Zhang, Wei,Zhang, Guolin,Wang, Chun
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p. 4822 - 4829
(2017/07/17)
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- Certain 4-iminoflavones derivatives: Synthesis, docking studies, antiasthmatic and antimicrobial agents
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In this present study, certain substituted 4-iminoflavone derivatives 5(a-j) were synthesized. All the synthesized compounds were evaluated for antiasthmatic and antimicrobial activity. Among the synthesized compounds, 5f was found to be the most promising against asthmatic models, whilst, 5h was found active against all the microbial strains. Antiasthmatic activity was correlated and evaluated with various models, e.g., citric acid induced cough model, OVA induced asthma model (biochemical estimation for cell infiltrations, estimation of lipid peroxidation and glutathione and estimation of TNF-α and IL-6 and histamine induced response). Compound 5f was found to show 2.20 ± 0.047 number of cough whilst codeine showed 1.40 ± 0.548; compound 5f produced considerable reduction in neutrophils, lymphocytes, eosinophils and leukocytes; decrease in LPO level (lung and BALF) and increment in GSH level (lungand BALF); and decreased the level of TNF-α and IL-6, respectively. On the other hand, 5h showed MIC 6.25 μg/mL against B. subtilis and S. aureus, 3.1 μg/mL against E. coli, 1.55 μg/mL against S. typhi and 6.25 μg/mL against C. albicans, respectively. In addition to gain better understanding on the biological activities of synthesized compounds, molecular docking study was performed within the binding site of human histamine H1 receptor and Glc-6-P synthase revealing compound 5f and 5h as best fit within the respective receptor pockets.
- Khah, Shaila,Goyal, Rohit,Chabba, Ankush,Jaiswal, Varun,Sharma, Gaurav,Naushad
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p. 1687 - 1696
(2016/07/06)
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- 2-substituted benzopyran-4-one compounds and application thereof
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The invention relates to the technical field of medicine and discloses 2-substituted benzopyran-4-one compounds with a structure shown in general formula I and an application of the compounds in preparation of antifungal drugs and synergistic antifungal drugs. The compounds can be jointly used with azole antifungal drugs, can improve sensibility of drug-resistance bacteria to the azole drugs, reverses drug resistance and produces a synergistic antifungal function.
- -
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Paragraph 0198
(2016/10/08)
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- Origin of Spectral Features and Acid-Base Properties of 3,7-Dihydroxyflavone and Its Monofunctional Derivatives in the Ground and Excited States
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Comprehensive spectral investigations of 3,7-dihydroxyflavone and its two derivatives, which each contain a methyl-blocked hydroxyl group, reveal complex radiation absorption in the 300-450 nm range and emission in the 370-650 nm range. The absorption and fluorescence characteristics of these compounds depend on the pH/H0 of the water/methanol media, which is caused by the existence of the compounds in various protolytic (cationic, neutral, anionic) and tautomeric forms. Combined analysis of steady-state, time-dependent and fluorescence decay spectral data enabled the identification of the emitting species, determination of their lifetimes with respect to radiative and nonradiative deactivation processes, fluorescence quantum yields, protolytic and tautomeric abilities under various conditions, and acidic dissociation constants of the cationic, neutral, and anionic forms of the compounds. Results of calculations carried out at the DFT and TD DFT levels of theory generally confirmed the experimental findings concerning tautomeric/protolytic transformations and equilibria. Computational methods also provided insight into possible tautomerization pathways. Electronically excited molecules are generally much more susceptible to tautomerization and acidic dissociation than ground-state ones. 3,7-Dihydroxyflavone exhibits distinguishable features among the compounds investigated and can be considered as potential spectral indicator of properties (polarity, hydrophobicity, hydrogen-bonding ability) and acidity/basicity of liquid environments.
- Serdiuk, Illia E.,Roshal, Alexander D.,B?azejowski, Jerzy
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p. 4325 - 4337
(2016/07/11)
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- 3-substituted propyl-2-alkene-1-ketone compound and application thereof
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The invention relates to the technical field of medicine and particularly discloses a 3-substituted propyl-2-alkene-1-ketone compound and application thereof to preparation of antifungal drugs and synergistic antifungal drugs. The compound can be used tog
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Paragraph 0106; 0107; 0108; 0109; 0110; 0111; 0112; 0113
(2016/10/09)
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- The synthesis and synergistic antifungal effects of chalcones against drug resistant Candida albicans
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To identify effective and low toxicity synergistic antifungal compounds, 24 derivatives of chalcone were synthesized to restore the effectiveness of fluconazole against fluconazole-resistant Candida albicans. The minimal inhibitory concentration (MIC80) and the fractional inhibitory concentration index (FICI) of the antifungal synergist fluconazole were measured against fluconazole-resistant Candida albicans. This was done via methods established by the clinical and laboratory standards institute (CLSI). Of the synthesized compounds, 2′-hydroxy-4′-methoxychalcone (8) exhibited the most potent in vitro (FICI = 0.007) effects. The structure activity relationship of the compounds are then discussed.
- Wang, Yuan-Hua,Dong, Huai-Huai,Zhao, Fei,Wang, Jie,Yan, Fang,Jiang, Yuan-Ying,Jin, Yong-Sheng
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supporting information
p. 3098 - 3102
(2016/06/13)
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- Single and double intramolecular proton transfers in the electronically excited state of flavone derivatives
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In an attempt to create a flavone derivative able to take part in Excited State Intramolecular Double Proton Transfer (ESIDPT), we synthesized two carbonyl derivatives of 3,7-dihydroxyflavone, both containing two different proton-transfer sites as well as related carbonyl derivatives of 3-hydroxyflavone and 7-hydroxyflavone. All the examined hydroxyflavones were found to participate in the Excited State Intramolecular Proton Transfer (ESIPT). ESIPT which involves 3-hydroxyl and 4-carbonyl groups was found to have a higher barrier compared to ESIPT involving 7-hydroxyl and 6/8-carbonyl fragments. According to the data presented, 3,7-dihydroxy-2-phenyl-6-(3-phenylpropanoyl)-4H-chromen-4-one undergoes a two-stage ESIDPT with formation of an intermediate tautomer. This kind of ESIDPT leads to a tautomeric form with an abnormally low rate of radiative deactivation of the excited state, which conditions low fluorescence quantum yield. The behavior of 3,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde in the electronically excited state is similar to 3-hydroxyflavone derivatives, thus we conclude the occurrence of a single ESIPT in this compound.
- Serdiuk,Roshal
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p. 102191 - 102203
(2015/12/11)
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- Steroid Sulfatase Inhibitors Based on Phosphate and Thiophosphate Flavone Analogs
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Preclinical Research A series of phosphate and thiophosphate flavone derivatives were synthesized and biologically evaluated in vitro for inhibition of steroid sulfatase (STS) activity. The described synthesis includes the straightforward preparation of 7-hydroxy-2-phenyl-4H-chromen-4-one 3a, 2-(4-fluorophenyl)-7-hydroxy-4H-chromen-4-one 3b, 7-hydroxy-2-(4-(trifluoromethyl)phenyl)-4H-chromen-4-one 3c, 7-hydroxy-2-(p-tolyl)-4H-chromen-4-one 3d modified with different phosphate or thiophosphate moieties. The inhibitory properties of the synthesized compounds were tested against human placenta STS. Some of the novel STS inhibitors had good activities against STS. In particular, the bis-(4-oxo-2-(p-tolyl)-4H-chromen-7-yl) hydrogenthiophosphate, 6i had the most potent inhibitory effect with an IC50 value of 3.25 μM as compared to an IC50 value of 8.50 μM for the 2-(4-trifluoromethylphenyl)-chromen-4-one-7-O-sulfamate used as a reference. Drug Dev Res 76: 450-462, 2015.
- Kozak, Witold,Dako, Mateusz,Maslyk, Maciej,Kubiski, Konrad,Rachon, Janusz,Demkowicz, Sebastian
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p. 450 - 462
(2016/01/28)
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- Synthesis and evaluation of neuroprotective selenoflavanones
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The physicochemical properties and antioxidant activity of a molecule could be improved by the substitution of an oxygen atom in a molecule with selenium. We synthesized selenoflavanones and flavanones to evaluate their neuroprotective effects. The selenoflavanones showed improved physicochemical properties, suggestive of the ability to pass through the blood-brain barrier (BBB). They showed in vitro antioxidant effects against hydrogen peroxide, and did not result in severe cytotoxicity. Moreover, infarction volumes in a transient ischemia mouse model were significantly reduced by the selenoflavanone treatments.
- Choi, Yong-Sung,Kim, Dong-Myung,Kim, Yoon-Jung,Yang, Sai,Lee, Kyung-Tae,Ryu, Jong Hoon,Jeong, Jin-Hyun
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p. 29574 - 29582
(2015/12/23)
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- Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold
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The effect of aryl substitution on various aspects of the interconversion of ortho-hydroxychalcones and flavanones has been studied using multiple spectroscopic techniques. Derivatization of the core scaffold predictably alters the midpoint pH of this equilibration process suggesting its viability for application as a functional colorimetric molecular switch.
- Muller, Brian M.,Mai, Jesse,Yocum, Reid A.,Adler, Marc J.
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p. 5108 - 5114
(2014/07/08)
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- Quantum-chemical analysis of the Algar-Flynn-Oyamada reaction mechanism
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This work is devoted to improving the understanding of Algar-Flynn-Oyamada reaction mechanism and the analysis of factors that affect the formation of flavonols. The calculation of thermodynamic parameters for the key reaction steps pointed to a mechanism involving chalcone epoxides as intermediates. A correlation was identified between the nucleophilicity of oxygen atom at position 2' of epoxide anions and the yields of flavonols. An increased charge at the nucleophilic center was shown to reduce the effectiveness of β-cyclization of epoxide anions.
- Serdiuk,Roshal,B?a?ejowski
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p. 396 - 403
(2014/08/05)
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- Enantioselective selenocyclization via dynamic kinetic resolution of seleniranium ions by hydrogen-bond donor catalysts
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Highly enantioselective selenocyclization reactions are promoted by the combination of a new chiral squaramide catalyst, a mineral acid, and an achiral Lewis base. Mechanistic studies reveal that the enantioselectivity originates from the dynamic kinetic resolution of seleniranium ions through anion-binding catalysis.
- Zhang, Hu,Lin, Song,Jacobsen, Eric N.
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supporting information
p. 16485 - 16488
(2015/01/09)
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- Microwave-assisted synthesis and tyrosinase inhibitory activity of chalcone derivatives
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A series of chalcones and their derivatives were synthesized, and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that some of the synthesized compounds exhibited significant inhibitory activity, and four compounds exhibited more potent tyrosinase inhibitory activity than the reference standard inhibitor kojic acid (5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one). Specifically, 1-(-1-(4-methoxyphen- yl)-3-phenylallylidene)thiosemicarbazide (18) exhibited the most potent tyrosinase inhibitory activity with IC50 value of 0.274 μm. The inhibition mechanism analysis of 1-(-1-(2,4-dihydroxyphenyl)-3-phenylallylidene) thiosemicarbazide (16) and 1-(-1-(4-methoxyphenyl)-3-phenylallylidene) thiosemicarbazide (18) demonstrated that the inhibitory effects of the two compounds on the tyrosinase were irreversible. Preliminary structure activity relationships' analysis suggested that further development of such compounds might be of interest.
- Liu, Jinbing,Chen, Changhong,Wu, Fengyan,Zhao, Liangzhong
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- Towards a dynamic covalent molecular switch: Substituent effects in chalcone/flavanone isomerism
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Chalcone/flavanone interconversion occurs facilely under aqueous alkaline conditions making it a promising scaffold for the development of a covalent molecular switch. In this study, a single methoxy substituent is shown to have a significant impact on the equilibrium dynamics of this reaction; this impact is dependent on the site of substitution. The Royal Society of Chemistry.
- Mai, Jesse,Hoxha, Ermal,Morton, Caitlin E.,Muller, Brian M.,Adler, Marc J.
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supporting information
p. 3421 - 3423
(2013/07/04)
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- Simple and efficient one step synthesis of functionalized flavanones and chalcones
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A facile and highly efficient microwave-assisted synthesis of functionalized chalcones and flavanones based on the Claisen-Schmidt condensation reaction is reported. The method describes the synthesis of flavanones in single step with excellent yield and it was revealed that position and number of substituents on acetophenones and aromatic aldehydes played a very crucial and key role in the construction of flavanone derivatives. Among the thirty two synthesized compounds, five chalcones and one flavanone were novel compounds.
- Albogami, Abdullah Saad,Karama, Usama,Mousa, Ahmed Amine,Khan,Al-Mazroa, Sara Abdullah,Alkhathlan, Hamad Z.
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p. 619 - 626
(2012/10/30)
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- Arylalkyl ketones, benzophenones, desoxybenzoins and chalcones inhibit TNF-α induced expression of ICAM-1: Structure-activity analysis
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The interaction between leukocytes and the vascular endothelial cells (EC) via cellular adhesion molecules plays an important role in the pathogenesis of various inflammatory and autoimmune diseases. Small molecules that block these interactions have been targeted as potential therapeutic agents against acute and chronic inflammatory diseases. In an effort to identify potent intercellular cell adhesion molecule-1 (ICAM-1) inhibitors, a large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones and their analogs (54 in total) have been synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated the possible mechanism for their ICAM-1 inhibitory activities. The most active compound was found to be 79. A large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones as well as their analogs (54 in total) were synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated a possible mechanism of their ICAM-1 inhibitory activities. The most active compound was found to be 79. Copyright
- Kumar, Sarvesh,Reddy L, Chandra Shekhar,Kumar, Yogesh,Kumar, Amit,Singh, Brajendra K.,Kumar, Vineet,Malhotra, Shashwat,Pandey, Mukesh K.,Jain, Rajni,Thimmulappa, Rajesh,Sharma, Sunil K.,Prasad, Ashok K.,Biswal, Shyam,Van Der Eycken, Erik,Depass, Anthony L.,Malhotra, Sanjay V.,Ghosh, Balaram,Parmar, Virinder S.
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experimental part
p. 368 - 377
(2012/07/31)
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- Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein
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Breast cancer resistance protein (BCRP/ABCG2) belongs to the ATP binding cassette family of transport proteins. BCRP has been found to confer multidrug resistance in cancer cells. A strategy to overcome resistance due to BCRP overexpression is the investigation of potent and specific BCRP inhibitors. The aim of the current study was to investigate different multi-substituted chalcones for their BCRP inhibition. We synthesized chalcones and benzochalcones with different substituents (viz. OH, OCH3, Cl) on ring A and B of the chalcone structure. All synthesized compounds were tested by Hoechst 33342 accumulation assay to determine inhibitory activity in MCF-7 MX and MDCK cells expressing BCRP. The compounds were also screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity in the calcein AM accumulation assay and were found to be selective towards inhibition of BCRP. Substituents at position 2′ and 4′ on chalcone ring A were found to be essential for activity; additionally there was a great influence of substituents on ring B. Presence of 3,4-dimethoxy substitution on ring B was found to be optimal, while presence of 2- and 4-chloro substitution also showed a positive effect on BCRP inhibition.
- Juvale, Kapil,Pape, Veronika F.S.,Wiese, Michael
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experimental part
p. 346 - 355
(2012/03/09)
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- Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics
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A total of 30 chalcone analogues was synthesized via a base catalyzed Claisen Schmidt condensation and screened for their in vitro antibacterial activity against Methicillin-sensitive Staphylococcus aureus (MSSA) and Methicillin-resistant Staphylococcus aureus (MRSA) alone or in combination with non beta-lactam antibiotics namely ciprofloxacin, chloramphenicol, erythromycin, vancomycin, doxycycline and gentamicin. In the checkerboard technique, fractional inhibitory concentration indices (FICI) show that the following combinations like ciprofloxacin with 25 (4′-bromo-2-hydroxychalcone); doxycycline with 21 (4-hydroxychalcone); doxycycline with 25; and doxycycline with 4 (2′,2-dihydroxychalcone) were synergistic against MRSA. In term SAR study, the relationship between chalcone structure and their antibacterial activity against S. aureus and synergy with tested antibiotics were discussed. Possible mechanisms for antibacterial activity of chalcones alone as well as the synergistic effect in combinations were proposed by molecular modeling studies, respectively. Combinations of chalcones with conventional antibiotics could be an effective alternative in the treatment of infection caused by MRSA.
- Tran, Thanh-Dao,Do, Tuong-Ha,Tran, Ngoc-Chau,Ngo, Trieu-Du,Huynh, Thi-Ngoc-Phuong,Tran, Cat-Dong,Thai, Khac-Minh
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experimental part
p. 4555 - 4560
(2012/08/07)
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- In vitro inhibitory properties of ferrocene-substituted chalcones and aurones on bacterial and human cell cultures
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Two series of ten chalcones and ten aurones, where ferrocene replaces the C ring and with diverse substituents on the A ring were synthesized. The compounds were tested against two antibiotic-sensitive bacterial strains, E. coli ATCC 25922 and S. aureus ATCC 25923, and two antibiotic-resistant strains, S. aureus SA-1199B and S. epidermidis IPF896. The unsubstituted compound and those with methoxy substitution showed an inhibitory effect on all bacterial strains at minimum inhibitory concentrations ranging between 2 and 32 mg L -1. For four of these compounds, the effect was bactericidal, as opposed to bacteriostatic. The corresponding organic aurones did not show growth inhibition, underscoring the role of the ferrocene group. The methoxy-substituted aurones and the unsubstituted aurone also showed low micromolar (IC50) activity against MRC-5 non-tumoral lung cells and MDA-MB-231 breast cancer cells, suggesting non-specific toxicity.
- Tiwari, Keshri Nath,Monserrat, Jean-Philippe,Hequet, Arnaud,Ganem-Elbaz, Carine,Cresteil, Thierry,Jaouen, Gerard,Vessieres, Anne,Hillard, Elizabeth A.,Jolivalt, Claude
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experimental part
p. 6451 - 6457
(2012/09/21)
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- Synthesis and antimalarial evaluation of novel benzopyrano[4,3-b]benzopyran derivatives
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7-Methoxyflavenes and 5,7,8-trimethoxyflavenes were found to undergo stereoselective acid-catalyzed rearrangement to generate the benzopyrano[4,3-b]benzopyran ring system present in the natural product, dependensin. Dependensin and its analogs were subjected to antimalarial growth inhibition assays against Plasmodium falciparum and found to have IC 50 values ranging between 1.9 and 3.9 μM.
- Devakaram, Ruth,Black, David Stc.,Andrews, Katherine T.,Fisher, Gillian M.,Davis, Rohan A.,Kumar, Naresh
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experimental part
p. 5199 - 5206
(2011/10/09)
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- Ionic liquid mediated Cu-catalyzed cascade oxa-Michael-oxidation: Efficient synthesis of flavones under mild reaction conditions
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Flavonoids are a class of natural products, found in a wide range of vascular plants and dietary components. Their low toxicity and extensive biological activities, including anti-cancer and anti-bacterial, have made them attractive candidates to serve as therapeutic agents for many diseases. Herein, we disclose a highly efficient synthetic method of CuI-catalyzed cascade oxa-Michael-oxidation, using chalcones as substrates, mediated by the ionic liquid [bmim][NTf2] at a low temperature. This efficient synthetic method has demonstrated high synthetic utility and can afford flavones in good to high yields (up to 98%).
- Du, Zhiyun,Ng, Huifen,Zhang, Kun,Zeng, Huaqiang,Wang, Jian
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supporting information; experimental part
p. 6930 - 6933
(2011/11/04)
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- Synthesis and antibacterial activity of chalcones bearing prenyl or geranyl groups from Angelica keiskei
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Chalcones bearing prenyl or geranyl groups from Angelica keiskei, such as 4-hydroxyderricin (1a), xanthoangelol (1e), xanthoangelol F (1f), xanthoangelol H (2), deoxyxanthoangelol H (3), and deoxydihydroxanthoangelol H (4) and their derivatives were synthesized. From the evaluation of antibacterial activity of the synthesized chalcones, 1a, isobavachalcone (1b), 1e, 1f, bavachalcone (5a), and broussochalcone B (5b) were found to inhibit Gram-positive bacteria.
- Sugamoto, Kazuhiro,Matsusita, Yoh-Ichi,Matsui, Kana,Kurogi, Chiaki,Matsui, Takanao
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p. 5346 - 5359
(2011/08/04)
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- Solution phase photocyclisation reaction of 2-hydroxychalcones to 4-flavanones
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The photochemical cyclisation of 2-hydroxychalcones leading to the synthesis of 4-flavanones in solution phase has been investigated. The formation of photoproducts has been explained on the basis of excited state intramolecular proton transfer (ESIPT) and the cyclisation efficiency of the chalcones has been found to depend upon the electron density on the phenolic oxygen as well as on the carbonyl group. This synthesis of flavanones by photoirradiation is an eco-friendly route with comparative yield to those of thermal methods. Although the molecular skeletons of these substrates is amenable to cis-trans isomerisations and cycloadditions but no photoproducts corresponding to these reactions have been realized.
- Kamboj, Ramesh C.,Berar, Surinder,Berar, Urmila,Gupta, Satish C.
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experimental part
p. 879 - 885
(2012/04/04)
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- Selective synthesis of 3,4-dihydrocoumarins and chalcones from substituted aryl cinnamic esters
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Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by TiCl4. This method can be used for preparing various coumarin & chalcone compounds.
- Jeon, Jae-Ho,Yang, Deok-Mo,Jun, Jong-Gab
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experimental part
p. 65 - 70
(2011/10/31)
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- Synthesis of flavanones by use of anhydrous potassium carbonate as an inexpensive, safe, and efficient basic catalyst
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Anhydrous potassium carbonate has been utilized as an inexpensive, safe, and efficient basic catalyst for the synthesis of flavanones starting either from 2′-hydroxychalcones or from 2′-hydroxyacetophenones. In both the cases the favored reaction condition was either refluxing in a solvent with added catalyst or microwave irradiation on the catalyst.
- Mondal, Rina,Gupta, Arpita Das,Mallik, Asok K.
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experimental part
p. 5020 - 5024
(2011/10/19)
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- A new series of flavones, thioflavones, and flavanones as selective monoamine oxidase-B inhibitors
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A new series of synthetic flavones, thioflavones, and flavanones has been synthesized and evaluated as potential inhibitors of monoamine oxidase isoforms (MAO-A and -B). The most active series is the flavanone one with higher selective inhibitory activity against MAO-B. Some of these flavanones (mainly the most effective) have been separated and tested as single enantiomers. In order to investigate the MAOs recognition of the most active and selective compounds, a molecular modeling study has been performed using available Protein Data Bank (PDB) structures as receptor models for docking experiments.
- Chimenti, Franco,Fioravanti, Rossella,Bolasco, Adriana,Chimenti, Paola,Secci, Daniela,Rossi, Francesca,Yá?ez, Matilde,Orallo, Francisco,Ortuso, Francesco,Alcaro, Stefano,Cirilli, Roberto,Ferretti, Rosella,Sanna, M. Luisa
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experimental part
p. 1273 - 1279
(2010/04/24)
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- Synthesis and antiinflammatory activity of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide
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Nineteen new 2-pyrazoline bearing benzenesulfonamide derivatives were synthesized by condensing chalcones with 4-hydrazinonbenzenesulfonamide hydrochloride. Their chemical structures were proved by means of IR, 1H NMR, 13C NMR, mass spectroscopic and elemental analyses data. These compounds were tested at dose of 20 mg/kg for their anti-inflammatory activity in carrageenan-induced rat paw edema model and volume of paw edema was measured at 0, 3 and 5 h. Two compounds 3k and 3l were found to be more active than celecoxib throughout the study (at 3 and 5 h). While two other compounds 3m and 3n showed more potent activity than celecoxib at 5 h. They are devoid of ulcerogenic potential when administered orally at a dose of 60 mg/kg. Compounds (3k-m) showed COX-1 and COX-2 inhibitory activity at 0.05 μM.
- Rathish,Javed, Kalim,Ahmad, Shamim,Bano, Sameena,Alam,Pillai,Singh, Surender,Bagchi, Vivek
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scheme or table
p. 255 - 258
(2009/05/07)
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- Red fluorescence from tautomers of 2′-hydroxychalcones induced by intramolecular hydrogen atom transfer
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Tautomer fluorescence in the longer wavelength region at 600 nm produced by intramolecular hydrogen atom transfer was observed in several 2′-hydroxychalcones having an electron donating group at the para position of the phenyl ring. The quantum yield of tautomer fluorescence increased by 1000 times upon decreasing the temperature from room temperature to 77 K. The introduction of dendritic substituents also increased the intensity of the tautomer fluorescence. One can control the photochemical and photophysical properties of the olefins by introduction of intramolecular hydrogen bonding and photoinduced hydrogen atom transfer. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2009.
- Teshima, Takeshi,Takeishi, Madoka,Arai, Tatsuo
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experimental part
p. 1393 - 1401
(2009/09/25)
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- Enantioselective synthesis of chromanes by iridium-catalyzed asymmetric hydrogenation of 4H-chromenes
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Iridium complexes of chiral oxazoline-based P,N-ligands proved to be efficient catalysts for the enantioselective hydrogenation of 2-aryl- and 2-alkyl-4H-chromenes. The best results were obtained with a ligand derived from threonine (ThrePHOX), which induced ee values of 95% to >99% in the hydrogenation of 2-methyl-, 2-cyclohexyl- and various 2-aryl-substituted chromenes. Georg Thieme Verlag Stuttgart.
- Valla, Carine,Baeza, Alejandro,Menges, Frederik,Pfaltz, Andreas
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scheme or table
p. 3167 - 3171
(2009/06/17)
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- Nitrogen-containing flavonoid analogues as CDK1/cyclin B inhibitors: Synthesis, SAR analysis, and biological activity
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A series of nitrogen-containing flavonoid analogues were designed and synthesized by Mannich reaction, and screened for the inhibitory activities of cyclin-dependent kinases using a FRET-based biochemical assay method. The results showed that C-8 nitrogen-containing baicalein analogues 3a-3f exhibited potent CDK1/Cyclin B inhibitory activities. 5,6,7-Trihydroxy-8-(dimethylaminomethyl)-2-phenyl-4H-chromen-4-one 3a, 5,6,7-trihydroxy-8-(pyrrolid inylmethyl)-2-phenyl-4H-chromen-4-one 3b, and 5,6,7-trihydroxy-8-(piperidinylmethyl)-2-phenyl-4H-chromen-4-one 3c (IC50 1.05-1.28 μM) were about sixfold more potent than baicalein 2 (IC50 6.53 μM). 5,6,7-Trihydroxy-8-(morpholinomethyl)-2-phenyl-4H-chromen-4-one 3d, 5,6,7-trihydroxy-8-(thiomorpholinomethy)-2-phenyl-4H-chrom en-4-one 3e, and 5,6,7-trihydroxy-8-(4-methylpiperazinylmethyl)-2-phenyl-4H-chromen-4-one 3f (IC50 0.27-0.38 μM) were about 20-fold more potent than baicalein, and were at the same level as flavopiridol (IC50 0.33 μM).
- Zhang, Shixuan,Ma, Jigang,Bao, Yongming,Yang, Puwen,Zou, Liang,Li, Kangjian,Sun, Xiaodan
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p. 7128 - 7133
(2008/12/22)
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- Synthesis of flavanones using nanocrystalline MgO
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The design and development of a truly nano heterogeneous catalyst for the Claisen-Schmidt condensation (CSC) of benzaldehydes with 2-hydroxyacetophenone to yield substituted chalcones followed by isomerization to afford flavanones with excellent yields and selectivity is described.
- Choudary,Ranganath,Yadav, Jagajit,Lakshmi Kantam
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p. 1369 - 1371
(2007/10/03)
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- New synthesis of flavanones catalyzed by L-proline
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L-Proline is utilized as an efficient organocatalyst for the synthesis of substituted flavanones and chalcones in good yields. The efficiency of the catalyst was proved with a variety of substrates ranging from electron-deficient to electron-rich aryl aldehydes and 2-hydroxyacetophenones.
- Chandrasekhar,Vijeender,Venkatram Reddy
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p. 6991 - 6993
(2007/10/03)
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- Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives
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A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr 3 in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3′,4′- dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production.
- Dao, Tran Thanh,Chi, Yeon Sook,Kim, Jeongsoo,Kim, Hyun Pyo,Kim, Sanghee,Park, Haeil
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p. 1165 - 1167
(2007/10/03)
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- Flavonoids: Structural requirements for antiproliferative activity on breast cancer cells
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Several classes of flavonoids (flavones, flavanones, 2′-hydroxychalcones and flavan-4-ols) having a variety of substituents on A ring were investigated for their antiproliferative activity against MCF-7 human breast cancer cells. Structure-activity relationships of these compounds were discussed. 2′-hydroxychalcones and methoxylated flavanones were found to be potent inhibitors of MCF-7 cells growth whereas flavones and flavan-4-ols appeared to be weak inhibitory agents except 7,8-dihydroxyflavone.
- Pouget, Christelle,Lauthier, Fabienne,Simon, Alain,Fagnere, Catherine,Basly, Jean-Philippe,Delage, Christiane,Chulia, Albert-Jose
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p. 3095 - 3097
(2007/10/03)
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- Effect of flavonol derivatives on the carrageenin-induced paw edema in the rat and inhibition of cyclooxygenase-1 and 5-lipoxygenase in vitro.
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Alkoxyflavonols were synthesized by the Algar-Flynn-Oyamada (AFO) cyclization of chalcones. Hydroxyflavonols were prepared by dealkylation of methoxyflavonols by refluxing in hydroiodic acid. The alkoxyflavonols 3-hydroxy-2-(2,3,4-trimethoxyphenyl)-4H-chr
- Sobottka,Werner,Blaschke,Kiefer,Nowe,Dannhardt,Schapoval,Schenkel,Scriba
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p. 205 - 210
(2007/10/03)
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- Condensation reactions in water of active methylene compounds with arylaldehydes. One-pot synthesis of flavonols
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The condensation reactions of acetophenone, cyclohexanone, isophorone, phenylacetonitrile, p-nitrophenylacetonitrile, (phenylsulfonyl)acetonitrile and indene with benzaldehyde were studied in water heterogeneous phase in the presence and absence of anionic and cationic surfactants such as SLS, CTACl, (CTA)2SO4 and CTAOH. All the reactions occur with excellent yields. The cationic surfactants favour the reaction and the comparison with the corresponding tetrabutylammonium salts show that the micellar catalysis is effective mainly towards the dehydration reaction following that of condensation. Anionic surfactant SLS is inactive. 2'-hydroxychalcones were prepared in aqueous medium in good-excellent yields and the one-pot synthesis of 7- and 3',4'-substituted flavonols was achieved.
- Fringuelli, Francesco,Pani, Giosanna,Piermatti, Oriana,Pizzo, Ferdinando
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p. 11499 - 11508
(2007/10/02)
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- 13C Nuclear Magnetic Resonance Studies on 1,3-Diphenylprop-2-enones
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The 13C NMR spectra of 48 differently substituted chalcones (1,3-diphenylprop-2-enones) have been recorded and the results are discussed.The data will be useful in the identification of new/natural chalcones.
- Parmar, V. S.,Sharma, Sunil,Rathore, J. S.,Garg, Meenu,Gupta, Sandhya,et al.
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p. 470 - 474
(2007/10/02)
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