Microwave-Assisted Efficient Synthesis of Polymethoxyacetophenones and Natural Polymethoxyflavones, and Their Inhibitory Effects on Melanogenesis

Tsukayama, Masao; Kusunoki, Eiji; Hossain, Mohammad Mamun; Kawamura, Yasuhiko; Hayashi, Shinji

doi:10.3987/com-07-11054

Cited by 15 publications

(8 citation statements)

References 14 publications

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“…This involves more steps compared to the direct cyclization but still is very useful for a planned synthesis. A simple and green pathway is described for the synthesis of highly substituted flavones using a diketone through a number of protectiondeprotection steps [21].…”

Section: Resultsmentioning

confidence: 99%

Eco-friendly and simple synthesis of some non-natural flavones through chalcones

et al. 2018

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A distinctive feature of polyphenolics is the possession of biological properties such as antioxidant and antimicrobial activities. Simple synthesis and study about such important class of compounds and their analogs are very important to enhance the understanding of their role in human health and diseases. Accordingly, a series of chalcones (2a-f) have been synthesized by Claisen-Schmidt condensation reaction with required acetophenones and aromatic aldehydes in high yields. The conversion of chalcones to the corresponding flavones (1a-g) taking minimal amount of dimethyl sulfoxide with iodine in presence of sulfuric acid was carried out under microwave conditions in high yields.

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Section: Resultsmentioning

confidence: 99%

Eco-friendly and simple synthesis of some non-natural flavones through chalcones

et al. 2018

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“…100-102 °C (lit. 21 for another 4 h. After completion of the reaction, H 2 O (100 mL) was added and the mixture was stirred for another 1 h and extracted with dichloromethane (50 mL × 2). The organic layers were combined and washed sequentially with H 2 O (100 mL × 2), saturated sodium bicarbonate (100 mL × 2) and H 2 O (100 mL × 1).…”

Section: Methodsmentioning

confidence: 99%

“…100-102 °C (lit. 21 101-103 °C) 1 H NMR (500 MHz, DMSO-d 6 ) (δ, ppm): 2.48 (s, 3H, COCH 3 ), 3.80 (s, 3H, OCH 3 ), 3.82 (s, 3H, OCH 3 ), 3.85 (s, 3H, OCH 3 ), 6.12 (s, 1H, ArH), 6.13 (s, 1H, ArH). IR ν max (KBr/cm −1 ): 1704 (C=O).…”

Section: 46-trimethoxyacetophenone (2)mentioning

confidence: 99%

A novel Synthesis of Naringenin and Related Flavanones

Chen

Wang

et al. 2014

Journal of Chemical Research

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“…101-102 °C (lit. 16 101-103 °C) 1 2-Hydroxy-4,6-dimethoxyacetophenone (3): A solution of the compound 2 (4.2 g, 0.02 mol) in dichloromethane (20 mL) at approximately 0 °C was treated with 1 mol L -1 BCl 3 in dichloromethane (24 mL, 0.024 mol) dropwise for about 1 h, and then the reaction mixture was stirred at room temperature for another 1 h. H 2 O (100 mL) was added, the mixture was stirred for another hour and extracted with dichloromethane twice (50 mL × 2). The organic layers were combined and washed sequentially with H 2 O (100 mL × 2), saturated sodium bicarbonate (100 mL × 2) and H 2 O (100 mL × 1) and then dried with anhydrous sodium sulfate overnight.…”

Section: Methodsmentioning

confidence: 99%

Total Synthesis of Luteolin

Liu

Chen

et al. 2014

Journal of Chemical Research

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Luteolin is a naturally-occurring polyphenolic flavonoid compound which has received considerable attention because of its wide range of biological and pharmacological properties. Efficient methods are reported for preparing luteolin, based on the acylation of 1,3,5-trimethoxybenzene and condensation with 3,4-dimethoxybenzaldehyde or the reaction of 3,4-dimethoxycinnamic acid with 1,3,5-trimethoxybenzene. The first of these is the better method.The flavonoids are polyphenolic compounds possessing a C6-C3-C6 skeleton ( Fig. 1) 1 , which occur widely in fruits and vegetables, and exhibit a broad spectrum of interesting biological activities against cancer, cardiovascular, and neurodegenerative diseases. 2 They are divided into several subgroups based on structural differences in their ring C involving its oxidation state. 3 The A and B-rings of naturally occurring flavonoids are usually functionalised by OH, OMe, isoprenyl, and glycosyl groups. The OH and glycosyl residues can be further functionalised by acyl, glycosyl or other flavonoid moieties. 3 They exert antioxidant and biological activities due to their aromatic moieties and the presence of oxygen functions. Luteolin (Fig. 2) is a polyphenolic flavonoid compound which has attracted considerable attention owing to its biological and pharmacological activities. 4-6 However, only a small amount of luteolin is available for biological studies because it is difficult to obtain. Among the published syntheses of luteolin, 7-9 none is attractive for large-scale synthesis due to drawbacks such as the use of expensive starting materials that are not easily accessible. Therefore, a simple and efficient synthetic method of luteolin is very desirable. We now report an efficient synthetic route for the preparation of luteolin (Scheme 1) based on our previous work. [10][11][12][13][14][15] Results and discussion

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Microwave-Assisted Efficient Synthesis of Polymethoxyacetophenones and Natural Polymethoxyflavones, and Their Inhibitory Effects on Melanogenesis

Cited by 15 publications

References 14 publications

Eco-friendly and simple synthesis of some non-natural flavones through chalcones

Eco-friendly and simple synthesis of some non-natural flavones through chalcones

A novel Synthesis of Naringenin and Related Flavanones

Total Synthesis of Luteolin

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