- 7-Hydroxy-4-(4-methoxyphenyl)-3,4-dihydrocoumarin
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The heterocyclic ring of the title compound, C16H14O4, is in a half-chair conformation. The best planes through the two phenyl rings make an angle of 61.0(1) °. The packing of the molecules is stabilized by intermolecular
- Rajalakshmi,Jain, Niveta,Deepthi,Krishnamurthy,Pattabhi, Vasantha
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- Synthesis and biological evaluation of 4-arylcoumarins as potential anti-Alzheimer's disease agents
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Alzheimer's disease (AD) is a progressive neurological degenerative disease that has complex pathogenesis. A variety of studies in humans indicate that several enzymes inhibitors can be useful in the treatment of AD, including acetylcholinesterase (AchE), butyrylcholinesterase (BuChE) and monoamine oxidase (MAO). Various substituted 4-arylcoumarin derivatives were synthesised, and their activity in vitro were investigated, including AChE/BuChE inhibitory activity, MAO inhibitory activity, and antioxidant activity. Most of the compounds were found to exhibit high inhibitory activity, and individual compounds have extremely excellent activities. Therefore 4-arylcoumarins provides an idea for drugs design for the development of therapeutic or preventive agents for AD.
- Miao, Yuhang,Sun, Jie,Wang, Xiaojing,Yang, Jie,Yun, Yinling
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- Synthesis and biological evaluation of novel neoflavonoid derivatives as potential antidiabetic agents
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Various substituted neoflavonoid derivatives were synthesized using sulfated montmorillonite K-10 as a catalyst. This method is environmental friendly, sustainable and economical, convenient in isolation and purification processes, with little byproducts, using earth-abundant catalysts and has relatively high yield. Those neoflavonoid derivatives were screened for antioxidant, a-glucosidase inhibitory, aldose reductase 2 (ALR2) inhibitory and advanced glycation end-product formation inhibitory effects. Most compounds exhibited significant antioxidant and advanced glycation end-product (AGE) formation inhibitory activities. It was interesting to note that out of thirty compounds, 8k and 8l were found to have greater ALR2 inhibitory activity than the standard drug quercetin. The pharmacological studies suggested neoflavonoid with adjacent 7,8-dihydroxy groups were more effective in inhibiting ALR2. Antidiabetic activity studies had shown that compounds 8l and 8m were equipotent to the standard drug glibenclamide in vivo. In summary, the target compound 8l provided a potential drug design concept for the development of therapeutic or prophylactic agents of diabetes and diabetes complications.
- Wang, Bing,Li, Na,Liu, Teng,Sun, Jie,Wang, Xiaojing
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p. 34448 - 34460
(2017/07/22)
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- Synthesis and Hydroxyl Radical Scavenging Activity of 4-Aryl-3,4-Dihydrocoumarins
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Twelve 4-aryl-3,4-dihydrocoumarins were synthesized by the condensation of phenols with the corresponding substituted cinnamic acids in the presence of nitrobenzene and sulfated montmorillonite K-10. This method displayed the property of green chemistry w
- Li, Na,Wang, Bing,Sun, Jing-yong,Wang, Xiao-jing,Sun, Jie
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p. 860 - 865
(2017/10/07)
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- Preparation method of 3,4-dihydro-4-arylcoumarin compounds
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The invention relates to the field of chemical synthesis, and concretely relates to a preparation method of 3,4-dihydro-4-arylcoumarin compounds. The method is characterized in that: substituted benzaldehyde is used as an initial raw material, propane diacid is added, a reaction is carried out with catalysis of piperidine, and substituted phenyl acrylic acid derivatives are obtained; montmorillonite K-10 which is acidified by sulfuric acid is used as a catalyst, a reaction between the substituted phenyl acrylic acid derivatives and phenolic compounds is carried out with heating, and the 3,4-dihydro-4-arylcoumarin compounds are obtained. Compared with the prior art, the preparation method of the 3,4-dihydro-4-arylcoumarin compounds has the advantages of easily available and cheap raw materials, simple operation, recyclable catalyst, environmental protection, simple post-treatment, low production cost, good promotion application, etc.
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Paragraph 0036
(2016/11/14)
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- An efficient and fast synthesis of 4-aryl-3,4-dihydrocoumarins by (CF3SO3)3Y catalysis under microwave irradiation
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A new and efficient synthesis of eleven 4-aryl-3,4-dihydrocoumarins, in which six are new compounds, was performed using (CF3SO3)3Y as catalyst under microwave irradiation. The target compounds were obtained in good yields (68-80%) and remarkable time (7-20 min) when compared to the literature reports (1-40 h).
- Rodrigues-Santos, Cláudio E.,Echevarria, Aurea
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p. 4505 - 4508
(2008/02/03)
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- Synthetic and novel biocatalytic resolution studies on (±)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins
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Eleven (±)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins have been synthesised in two steps starting from the coupling of cinnamic acid/substituted cinnamic acid with appropriate phenols, followed by acetylation in 50-83% overall yields. All hydroxy- and acet
- Singh, Ishwar,Prasad, Ashok K.,Sharma, Ajendra K.,Saxena, Rajendra K.,Olsen, Carl E.,Cholli, Ashok L.,Samuelson, Lynne A.,Kumar, Jayant,Watterson, Arthur C.,Parmar, Virinder S.
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p. 529 - 538
(2007/10/03)
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- Microwave-assisted synthesis of derivatives of chromanones
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A variety of chromanones are prepared from resorcinol and phloroglucinol in four steps: two of these reactions are conducted under microwave irradiation, the synthesis of cinnamic acids and the cyclisation of N-cinnamoylazoles.
- Barbry,Champagne
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- β,β-dimethylacrylophenones : BF3.ET2O-POCl3 catalysed acylation of phenols using β, β-dimethylacrylic acid
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Boron trifluoride etherate - phosphoryl chloride reagent is a useful reagent for the condensation between phenols and β,β-dimethylacrylic acid. The main products are acrylophenones. But surprisingly hydroquinone gives mono and diacrylates.
- Jain, Niveta,Krishnamurty
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p. 1237 - 1241
(2007/10/03)
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- Uncatalyzed reaction of phenols and naphthols with methyl cinnamates. A simple synthesis of 4-arylchroman-2-ones and 1-arylbenzo[f]chroman-3-ones
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4-Arylchroman-2-ones and 1-arylbenzo[f]chroman-3-ones can be prepared in moderate to good yields by reaction of phenols or β-naphthols with p-substituted methyl cinnamates in o-xylene under reflux.
- Speranza, Giovanna,Di Meo, Antonella,Zanzola, Simona,Fontana, Gabriele,Manitto, Paolo
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p. 931 - 936
(2007/10/03)
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- Condensation of Phenols and Cinnamic Acids in Presence of Polyphosphoric Acid: A Novel Biogenetic-type Oxidative Self-cyclisation of p-Methoxycinnamic Acid to 7-Methoxycoumarin
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The course of PPA condensation/cyclisation of different phenols and cinnamic acids has been found to depend upon the nature of the substrate, stoichiometry, composition of PPA, and reaction condition.Condensation of phloroglucinol (50-70 deg C, 1 hr) with cinnamic acid in the presence of PPA leads to pinocembrin (I) (50percent) and 5-hydroxy-4,8-diphenyl-3,4,6,7-tetrahydro2H,6H-benzodipyran-2,6-dione (II) (14percent).This condensation reaction when carried out with resorcinol for 2 hr furnishes 7-hydroxyflavanone (III) (60percent).Condensation of resorcinol monomethyl ether affords 2'-hydroxy-4'-methoxychalcone (IV) (12percent) and 4'-hydroxy-2'-methoxychalcone (V) (40percent), but no flavanone derivative.Reaction of p-methoxycinnamic acid (in xylene), in the presence of PPA and resorcinol, however, yields 7-hydroxy-4-(4'-methoxyphenyl)-3,4-dihydrocoumarin (VI) (56percent); with resorcinol monomethyl ether the corresponding 7-methoxy derivative (VII) (44percent) is obtained.Further, p-methoxycinnamic acid undergoes self-condensation in the presence of 0.5 mol equiv of phloroglucinol or resorcinol to give p-methoxycinnamic anhydride (VIII) (only 4percent) or bis(methoxybenzal)acetone (IX) (50percent).Interestingly, in the presence of resorcinol monomethyl ether (0.5 mol equiv, 4hr) p-methoxycinnamic acid undergoes biogenetic-type oxidative self-cyclisation to form 7-methoxycoumarin (X) (80percent).A plausible mechanism for the formation of X has been suggested.
- Talapatra, Bani,Deb, Tulika,Talapatra, Sunil
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p. 1122 - 1125
(2007/10/02)
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