- In vitro photoprotective evaluation and development of novel nanoemulsion with chromone derivative
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Chromone derivatives exhibiting high absorbance values in the UVA/UVB region were synthesized, and their photoprotective properties were evaluated. Chromones were prepared according to known literature procedures and characterized by high resolution mass
- Amparo, Tatiane R.,Antunes, Amanda S.,Cazati, Thiago,Diogo, Gabriela M.,Dos Santos, Viviane M. R.,Gouveia, Ana Paula,Penido, Ricardo G.,Perasoli, Fernanda B.,Sousa, Lucas R. D.,Taylor, Jason G.,Vieira, Paula M. A.,dos Santos, Orlando D. H.
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p. 1813 - 1821
(2021/08/05)
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- Design, synthesis and biological evaluation of 2-Phenyl-4H-chromen-4-one derivatives as polyfunctional compounds against Alzheimer’s disease
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Polyfunctional compounds comprise a novel class of therapeutic agents for the treatment of multi-factorial diseases. A series of 2-Phenyl-4H-chromen-4-one and its derivatives (5a–n) were designed, synthesized, and evaluated for their poly-functionality against acetylcholinestrase (AChE) and advanced glycation end products (AGEs) formation inhibitors against Alzheimer’s disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit AChE AGEs formation with additional radical scavenging activity. Especially, 5m, 5b, and 5j displayed the greatest ability to inhibit AChE (IC50 = 8.0, 8.2, and 11.8 nM, respectively) and AGEs formation (IC50 = 55, 79, and 54 μM, respectively) with good antioxidant activity. Molecular docking studies explored the detailed interaction pattern with active, peripheral, and mid-gorge sites of AChE. These compounds, exhibiting such multiple pharmacological activities, can be further taken a lead for the development of potent drugs for the treatment of Alzheimer’s disease.
- Singh, Manjinder,Kaur, Maninder,Vyas, Bhawna,Silakari, Om
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p. 520 - 530
(2017/10/09)
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- Aldose reductase inhibitors for diabetic complications: Receptor induced atom-based 3D-QSAR analysis, synthesis and biological evaluation
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Herein, atom-based 3D-QSAR analysis was performed using receptor-guided alignment of 46 flavonoid inhibitors of aldose reductase (ALR2) enzyme. 3D-QSAR models were generated in PHASE programme, and the best model corresponding to PLS factor four (QSAR4), was selected based on different statistical parameters (i.e., Rtrain2, 0.96; Qtest2 0.81; SD, 0.26). The contour plots of different structural properties generated from the selected model were utilized for the designing of five new congener molecules. These designed molecules were duly synthesized, and evaluated for their in vitro ALR2 inhibitory activity that resulted in the micromolar (IC50 22 μM) activity of all molecules. Thus, the newly designed molecules having ALR inhibitory potential could be employed for the management of diabetic complications.
- Vyas, Bhawna,Singh, Manjinder,Kaur, Maninder,Bahia, Malkeet Singh,Jaggi, Amteshwar Singh,Silakari, Om,Singh, Baldev
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supporting information
p. 59 - 71
(2015/05/05)
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- A new synthesis of flavones and pyranoflavone by intramolecular photochemical Wittig reaction in water
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A new synthetic approach toward the synthesis of flavones and pyranoflavone has been developed by light induced intramolecular photochemical Wittig reaction in water onto aryloxycarbonyl groups and suitably substituted phosphonium bromides sans any phase transfer catalyst or promoter.
- Das, Jhantu,Ghosh, Somnath
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p. 7189 - 7194
(2012/01/05)
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- Efficient synthesis of nitroflavones by cyclodehydrogenation of 2prime;-hydroxychalcones and by the Baker-Venkataraman method
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Several nitroflavone derivatives were synthesized by cyclodehydrogenation of 2′-hydroxychalcones and by the Baker-Venkataraman approach, starting from 2′-hydroxyacetophenones and benzoic acid derivatives. Nitroflavones synthesised by the first synthetic a
- Barros, Ana I. R. N. A.,Silva, Artur M. S.
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p. 1505 - 1528
(2007/10/03)
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- Synthesis and antibacterial activity of substituted flavones, 4-thioflavones and 4-iminoflavones
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Synthesis of flavones, 4-thioflavones and 4-iminoflavones was carried out with the substitution of variable halogens, methyl, methoxy and nitro groups in the A, B and AB rings of the respective compounds and we also report here their antibacterial activity. Most of the synthesized compounds were found to be active against Escherichia coli, Bacillus subtilis, Shigella flexnari, Salmonella aureus, Salmonella typhi and Pseudomonas aeruginosa. Activity of 4-thioflavones and 4-iminoflavones was found to be higher than that of their corresponding flavone analogues. Investigated compounds having substituents like F, OMe and NO2 at 4′-position in ring-B exhibited enhanced activity and the presence of electronegative groups in the studied compounds showed a direct relationship to the antibacterial activity.
- Ullah Mughal, Ehsan,Ayaz, Muhammad,Hussain, Zakir,Hasan, Aurangzeb,Sadiq, Amina,Riaz, Muhammad,Malik, Abdul,Hussain, Samreen,Choudhary, M. Iqbal
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p. 4704 - 4711
(2007/10/03)
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- Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones
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3-Acylchromones and 3-acylflavones, readily available by acylation of 2′-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO 3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones.
- Clarke, David S.,Gabbutt, Christopher D.,Hepworth, John D.,Heron, B. Mark
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p. 5515 - 5519
(2007/10/03)
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- Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor
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A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands.
- Marder, Mariel,Zinczuk, Juan,Colombo, Maria I.,Wasowski, Cristina,Viola, Haydee,Wolfman, Claudia,Medina, Jorge H.,Ruveda, Edmundo A.,Paladini, Alejandro C.
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p. 2003 - 2008
(2007/10/03)
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- A new metal complex promoted system for highly selective synthesis of 4H-chromen-4-ones (chromones)
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Co(III)(salpr)(OH), a six coordinate cobalt Schiff base complex, promotes the highly selective conversion of 1-(o-hydroxyaryl)-1,3-diketones to 4H-chromen-4-ones under neutral conditions.
- Nishinaga,Ando,Maruyama,Mashino
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p. 839 - 841
(2007/10/02)
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- Syntheses of some New Heterocycles from 4'-Aminochromones. Part I
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Syntheses of some new pyrazoles from hitherto unknown 4'-aminochromones have been described.Their structures have been confirmed on the basis of elemental analysis and spectral data.
- Mazumdar, A. K. D.,Das, S. C.,Karmakar, P. K.,Saha, N. K.,Banerji, K. D.
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p. 761 - 764
(2007/10/02)
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- Epoxidation of Flavones by Dimethyldioxirane
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The synthesis of epoxides 2 by epoxidation of flavones 1 with isolated dimethyldioxirane (as acetone solution) at subambient temperatures is reported.These labile epoxides were isolated and completely characterized by UV, IR, 1H and 13C NMR, MS, and C,H analyses.Warming to room temperature led to rearrangement to afford quantitatively the 3-hydroxyflavones 3b,h,i,n.Treatment of the epoxides 2b,f with methanol led to the 3-hydroxy-2-methoxyflavanones 4b,f, as a mixture of cis and trans isomers.
- Adam, Waldemar,Golsch, Dieter,Hadjiarapoglou, Lazaros
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p. 7292 - 7297
(2007/10/02)
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- Structural Studies on Bio-active Compounds. Part 12. Tautomerism and Conformation of Aryl-substituted 1-(2-Hydroxyphenyl)-3-phenylpropane-1,3-diones in the Solid Phase and in Solution
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The tautomerism of a series of aryl-substituted 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-diones has been studied in deuteriochloroform solution by 1H n.m.r. techniques and, in the case of 1-(2-hydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione and 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropane-1,3-dione, in the solid state by X-ray crystallography.Of these compounds, most exist between 80 and 95percent in the enolised form in solution and 1-(2-hydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione adopts this tautomer in the crystal.However, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropane-1,3-dione is present as the diketone in the solid phase and enolises very slowly in solution. 1-(6-Benzoyloxy-2-hydroxyphenyl)-3-hydroxy-3-phenylprop-2-en-1-one is shown by 1H n.m.r. spectroscopy possibly to adopt a 'coiled' conformation in solution in deuteriochloroform.
- Cunningham, Bernadette D. M.,Lowe, Philip R.,Threadgill, Michael D.
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p. 1275 - 1284
(2007/10/02)
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- Pyridinium Chlorochromate in Organic Synthesis. A Facile and Selective Oxidative Cleavage of Enol Ethers
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Pyridinium chlorochromate (PCC) has been found to be selective reagent for the oxidative cleavage of enol ethers to esters or keto lactones in high yields.
- Baskaran, S.,Islam, I.,Raghavan, Malini,Chandrasekaran, S.
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p. 1175 - 1178
(2007/10/02)
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- Reactions of Carbonyl Compounds in Basic Solutions. Part 11. The Baker-Venkataraman Rearrangement
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The detailed mechanism of the Baker-Venkataraman rearrangement has been studied.The kinetics of the rearrangement of a series of 2-acetylphenyl 3- or 4-substituted benzoates and acetylnaphthyl benzoates catalysed by a basic 'non-nucleophilic' buffer in dimethyl sulphoxide have been measured.Studies of substituent effects, kinetic isotope effects, and acidity function correlations indicate a pathway involving pre-equilibrium formation of the carbanion, followed by rate-determining intramolecular nucleophilic attack.The methanolysis of the 2-acetylphenyl benzoates catalysed by methoxide in methanolic dimethyl sulphoxide has been similary investigated.In this case the pathway appears to involve neighbouring group participation by the ketonic carbonyl group.
- Bowden, Keith,Chehel-Amiran, Mohsen
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p. 2039 - 2044
(2007/10/02)
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- Synthesis and characterization of 2-(2-hydroxyphenyl)-4-aryl-1,5-benzodiazepines
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Four benzodiazepine derivatives, reported earlier by other authors, were resynthesized and characterized by NMR, IR, GC/MS and elemental analysis. Three of the four compounds have melting points different from those initially reported by 35-70° C. The dif
- Lin,Hoch
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p. 640 - 642
(2007/10/02)
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- Synthesis of Some New Heterocycles from 4'-Amino Flavone
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A convenient synthesis, with good yields, for 4'-amino flavone (VI) using sodium dithionite as a reducing agent is presented.A few disubstituted thioureas (VIIa, b, c) have been prepared from VI. 4'-Hydrazino-flavone (IX) has been synthesised for the firs
- Fernandes, Peter S.,Coutinho, Louis
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p. 864 - 866
(2007/10/02)
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