- Iodine-mediated direct synthesis of 3-iodoflavones
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Molecular iodine has been used for the regioselective, one pot, direct synthesis of 3-iodoflavones from 2′-allyloxy chalcones, 2′-hydroxy chalcones and flavones. Allyl deprotection, cyclization dehydrogenation and α-iodination of 2′-allyloxychalcones has been achieved in a single step to offer 3-iodoflavones.
- Patil, Avinash M.,Kamble, Dayanand A.,Lokhande, Pradeep D.
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p. 1299 - 1307
(2018/04/05)
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- Synthesis and Screening of Human Monoamine Oxidase-A Inhibitor Effect of New 2-Pyrazoline and Hydrazone Derivatives
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A group of 3,5-diaryl-2-pyrazoline and hydrazone derivatives was prepared via the reaction of various chalcones with hydrazide compounds in ethanol. Twenty original compounds were synthesized. Ten of these original compounds have a pyrazoline structure, n
- Evranos-Aks?z, Begüm,Baysal, Ipek,Yabano?lu-?ift?i, Samiye,Djikic, Teodora,Yelek?i, Kemal,U?ar, Gülberk,Ertan, Rahmiye
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p. 743 - 756
(2015/10/12)
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- Design and synthesis of chalcone derivatives as potent tyrosinase inhibitors and their structural activity relationship
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Browning of fruits and vegetables is a serious issue in the food industry, as it damages the organoleptic properties of the final products. Overproduction of melanin causes aesthetic problems such as melisma, freckles and lentigo. In this study, a series of chalcones (1-10) have been synthesized and examined for their tryrosinase inhibitory activity. The results showed that flavokawain B (1), flavokawain A (2) and compound 3 were found to be potential tyrosinase inhibitors, indicating IC50 14.20-14.38 μM values. This demonstrates that 4-substituted phenolic compound especially at ring A exhibited significant tyrosinase inhibition. Additionally, molecular docking results showed a strong binding affinity for compounds 1-3 through chelation between copper metal and ligands. The detailed molecular docking and SARs studies correlate well with the tyrosinase inhibition studies in vitro. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and single X-ray crystallographic techniques. These findings could lead to design and discover of new tyrosinase inhibitors to control the melanine overproduction and overcome the economic loss of food industry.
- Akhtar, Muhammad Nadeem,Sakeh, Nurshafika M.,Zareen, Seema,Gul, Sana,Lo, Kong Mun,Ul-Haq, Zaheer,Shah, Syed Adnan Ali,Ahmad, Syahida
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- Absorption and fluorescent studies of 3-hydroxychromones
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The synthesis and spectral studies of variously substituted 3-hydroxychromones have been carried out. A key relationship between the structural motif of synthesized 3-hydroxychromones (3-HCs) and their fluorescent properties was found. The chromones substituted with electron-donating group at 4′-position expressed the red shift of the N and T band and also exhibited the increased fluorescent intensity ratio while the chromones with electron-withdrawing group showed the blue shift of the N and T band. Therefore, these 3-HCs may behave as the possible fluorescent probes.
- Khanna, Radhika,Kumar, Ramesh,Dalal, Aarti,Kamboj, Ramesh C.
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p. 1159 - 1163
(2015/10/20)
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- Discovery of 2′-hydroxychalcones as autophagy inducer in A549 lung cancer cells
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A series of 2′-hydroxychalcone derivatives was synthesized and the effects of all the compounds on growth of A549 lung cancer cell were investigated. The results showed that all compounds had inhibitory effects on the growth of A549 lung cancer cells and compound 2-7 possessed the highest growth inhibitory effect and induced autophagy of A549 lung cancer cells.
- Wang, Fang-Wu,Wang, Sheng-Qing,Zhao, Bao-Xiang,Miao, Jun-Ying
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p. 3062 - 3070
(2014/05/06)
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- COMPOSITION FOR TREATING DIABETES AND METABOLIC DISEASES AND A PREPARATION METHOD THEREOF
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Disclosed is a chalcone composition for treating diabetes and metabolic syndromes. In particular, the chalcone compound bound with 2-halogen in ring A significantly decreases the blood glucose level in the in vitro anti-diabetic effect experiment. In the in vivo animal model, the leading chalcone compound can prevent the progression of diabetes and control the blood glucose level, and there is no significant difference in the gains in body weight. Throughout the seven-week administration, there are no hepatic or renal toxicity observed.
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Paragraph 0029
(2013/03/26)
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- Synthesis and biological activities of some flavones
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Chalcones are synthesized by a base catalyzed Claisen Schmidt condensation reaction and then treated with dimethylsulphoxide in presence of iodine to get flavones. The synthesized compounds were evaluated for their antibacterial activity against Escherichia coilt P. aeruginosa, S. epidermidis and B. subtilis. All the flavones showed moderate to good activity. The structures of these compounds were confirmed by IR, UV, 1H NMR, Mass and elemental analysis.
- Sawant,Gill,Nirwan
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- Synthesis and biological activities of some flavones
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Chalcones are synthesized by a base catalyzed Claisen Schmidt condensation reaction and then treated with dimethylsulphoxide in presence of iodine to get flavones. The synthesized compounds were evaluated for their antibacterial activity against Escherichia coli, P. aeruginosa, S. epidermidis and B. subtilis. All the flavones showed moderate to good activity. The structures of these compounds were confirmed by IR, UV, 1H NMR, Mass and elemental analysis.
- Sawant,Gill,Nirwan
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p. 297 - 300
(2013/09/24)
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- An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4
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2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl 4 are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group. 2012 Elsevier Ltd. All rights reserved.
- Maiti, Gourhari,Kayal, Utpal,Karmakar, Rajiv,Bhattacharya, Rudraksha N.
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p. 6321 - 6325,5
(2012/12/12)
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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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- Synthesis and biological activities of some new quinoxalines
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The condensation of 5-chloro-2-hydroxyacetophenone 1 with different substituted aromatic aldehydes in ethanol in presence of strong alkali furnished 1-(2-hydroxy-5-chlorophenyl)-3-aryl propen-1-ones 2a-e. Bromination of compounds 2a-e in acetic acid gave 1-(2-hydroxy-5-chlorophenyl)-3-aryl 2,3-dibromopropan-1-ones 3a-e which upon treatment with o-phenylenediamine in methanol in presence of cone sulphuric acid underwent cyclization and resulted in the formation of quinoxaline derivatives 4ae. Structures of compounds were established on the basis of analytical and spectral studies. Further these compounds were evaluated for their antimicrobial activities and some selected compounds were evaluated for antitubercular activities.
- Basawaraj, Raga,Alvi, Shah Nadeemuddin,Chillargi, Neelavati,Gahininath, Wadikar,Zaheeruddin
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p. 147 - 150
(2013/09/24)
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- A two step synthesis of BzR/GABAergic active flavones via a Wacker-related oxidation
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A general route for the synthesis of biologically important flavones is reported via a two step sequence employing a catalytic Wacker-Cook oxidation4b as the key step.
- Lorenz, Michael,Shahjahan Kabir,Cook, James M.
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experimental part
p. 1095 - 1098
(2010/04/05)
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- Synthesis and fungicidal evaluation of novel chalcone-based strobilurin analogues
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Strobilurin derivatives have become one of the most important classes of agricultural fungicide due to a novel action mode, wide fungicidal spectrum, lower toxicity toward mammalian cells, and environmentally benign characteristics. To discover new strobilurin analogues with high activity against resistant pathogens, a series of new chalcone-based strobilurin derivatives are designed and synthesized by integrating a chalcone scaffold with a strobilurin pharmacophore. The preliminary bioassay showed that some of the chalcone analogues exhibited good in vivo fungicidal activities against Pseudoperoniospora cubensis and Sphaerotheca fuliginea at the dosage of 200 μg mL-1. Two compounds, (£)-methyl 2-[2-({3-[(£)-3-(2- chlorophenyl)acryloyl]phenoxy}methyl)phenyl]-3-meth-oxyacrylate (1e) and (E)-methyl 2-[2-({3-[(E)-3-(3-bromophenyl)acryloyl]phenoxy}methyl)phenyl]-3- methoxyacrylate (11), were found to display higher fungicidal activities against P. cubensis (EC90 = 118.52 μg ml-1 for 1e and EC 90 = 113.64 μg mL-1 for 11) than Kresoxim-methyl (EC90 = 154.92 μg mL-1) and were identified as the most promising candidates for further study. The present work demonstrated that strobilurin analogues containing chalcone as a side chain could be used as a lead structure for further developing novel fungicides. To our knowledge, this is the first report about the syntheses and fungicidal activities of chalcone-based strobilurin derivatives.
- Zhao, Pei-Liang,Liu, Chang-Ling,Huang, Wei,Wang, Ya-Zhou,Yang, Guang-Fu
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p. 5697 - 5700
(2008/03/14)
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- Synthesis and PPAR-γ ligand-binding activity of the new series of 2′-hydroxychalcone and thiazolidinedione derivatives
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Fifteen chalcones and three thiazolidinedione (TZD) chalcones were prepared to evaluate their peroxisome proliferator-activated receptor-γ (PPAR-γ) ligand-binding activities. Among the three TZDs, one compound possessed PPAR-γ transactivation potential, while the others showed antagonistic activity against PPAR-γ transactivation. Among the chalcones, compound 5 was the most potent, and structure-activity relationship studies indicated that a methoxyl group in position C-4 and hydroxyl group in position C-4′ or 5′ in chalcone plays a key role in determining the potency of PPAR-γ activation.
- Sang, Hoon Jung,Soo, Young Park,Kim-Pak, Youngmi,Hong, Kyu Lee,Kyong, Soo Park,Kuk, Hyun Shin,Ohuchi, Kazuo,Shin, Hyun-Kyung,Sam, Rok Keum,Soon, Sung Lim
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p. 368 - 371
(2007/10/03)
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- Inhibitory effects of 2'-hydroxychalcones on rat lens aldose reductase and rat platelet aggregation
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Inhibitory effects of synthetic 2'-hydroxychalcone derivatives on rat lens aldose reductase (RLAR) and on platelet aggregation were investigated for the prevention or the treatment of chronic diabetic complications. 5'-chloro-4,2'-dihydroxychalcone (8) and 5'-chloro-3,2'-dihydroxychalcone (27) exhibited a potent inhibitory effect on rat platelet aggregation induced by ADP (IC50=0.10 and 0.06 mg/ml, respectively) and collagen (IC50=44 and 16 μg/ml, respectively) but showed relatively weak inhibitory activities on RLAR.
- Lim, Soon Sung,Jung, Sang Hoon,Ji, Jun,Shin, Kuk Hyun,Keum, Sam Rok
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p. 1786 - 1789
(2007/10/03)
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- 4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity
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4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5 μg/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.
- De Meyer,Haemers,Mishra,Pandey,Pieters,Vanden Berghe,Vlietinck
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p. 736 - 746
(2007/10/02)
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