Mechanically Activated Solid-State Synthesis of Flavones by High-Speed Ball Milling

Zhu, Xingyi; Li, Zhenhua; Shu, Qiangfeng; Zhou, Chenfeng; Su, Weike

doi:10.1080/00397910902898551

Cited by 25 publications

(9 citation statements)

References 27 publications

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“…White solid, yield: 85.3%； Rf = 0.52, MeOH:CH 2 Cl 2 = 1:10. It is a known compound (Ibrahim & Abul‐Hajj, 1990; Zhu, Li, Shu, Zhou, & Su, 2009). 1 H NMR (600 MHz, DMSO‐ d 6 ) δ (ppm):10.842 (s, 1H, OH), 8.077–8.061 (m, 2H, ArH), 7.894 (d, J = 8.7 Hz, 1H, ArH), 7.610–7.560 (m, 3H, ArH), 7.013 (d, J = 2.2 Hz, 1H, ArH), 6.937 (dd, J = 8.7, 2.2 Hz, 1H, ArH), 6.907 (s, 1H, CHCO).…”

Section: Methodsmentioning

confidence: 99%

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Nitrogen‐containing flavonoid and their analogs with diverse B‐ring in acetylcholinesterase and butyrylcholinesterase inhibition

Chen

Liu

et al. 2020

Drug Development Research

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In this study, a series of new flavones (2-phenyl-chromone), 2-naphthyl chromone, 2-anthryl-chromone, or 2-biphenyl-chromone derivatives containing 6 or 7-substituted tertiary amine side chain were designed, synthesized, and evaluated in acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition. The results indicated that the alteration of aromatic ring connecting to chromone scaffold brings about a significant impact on biological activity. Compared with flavones, the inhibitory activity of 2-naphthyl chromone, 2-anthryl-chromone derivatives against AChE significantly decreased, while that of 2-biphenyl chromone derivatives with 7-substituted tertiary amine side chain is better than relative flavones derivatives. For all new synthesized compounds, the position of tertiary amine side chain obviously influenced the activity of inhibiting AChE. The results above provide great worthy information for the further development of new AChE inhibitors. Among the newly synthesized compounds, compound 5a is potent in AChE inhibition (IC 50 = 1.29 ± 0.10 μmol/L) with high selectivity for AChE over BChE (selectivity ratio: 27.96). An enzyme kinetic study of compound 5a suggests that it produces a mixed-type inhibitory effect against AChE.

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Section: Methodsmentioning

confidence: 99%

“…White solid, yield: 85.3%； Rf = 0.52, MeOH:CH 2 Cl 2 = 1:10. It is a known compound (Ibrahim & Abul-Hajj, 1990;Zhu, Li, Shu, Zhou, & Su, 2009 25, 163.34, 162.74, 158.04, 132.17, 131.60, 129.65, 127.07, 126.64, 116.47, 115.73, 106.94…”

Section: General Procedures For the Synthesis Of Compounds 3a-3hmentioning

confidence: 99%

Nitrogen‐containing flavonoid and their analogs with diverse B‐ring in acetylcholinesterase and butyrylcholinesterase inhibition

Chen

Liu

et al. 2020

Drug Development Research

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“…The synthesis of flavones was accomplished by cyclodehydration of 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones in the presence of KHSO 4 by HSBM within 15 min (Scheme 1.42). 40 Kaupp and co-workers have reported the quantitative formation of sixmembered oxygen containing heterocycles by Michael addition followed by rearrangement and cyclization under ball milling (Scheme 1.43). 41 Quantitative yields of products were obtained without using any catalyst in a waste free manner.…”

Section: Oxygen-containing Heterocyclesmentioning

confidence: 98%

CHAPTER 1. Carbon–Heteroatom Bond Forming Reactions and Heterocycle Synthesis under Ball Milling

Ranu¹,

Chatterjee²,

Mukherjee³

2014

Green Chemistry Series

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“…Su and coworkers described an efficient solid-state KHSO 4catalyzed synthesis of flavones from 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones (Scheme 133). 153 The cyclodehydration was performed in a planetary centrifugal mill AGO-2 with a rotational speed of 1290 rpm (21.5 Hz) for 5-15 min to give flavones in 88-97% yields.…”

Section: Miscellaneous Mechanochemical Reactionsmentioning

confidence: 99%

Mechanochemical organic synthesis

2013

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Recently, mechanical milling using a mixer mill or planetary mill has been fruitfully utilized in organic synthesis under solvent-free conditions. This review article provides a comprehensive overview of various solvent-free mechanochemical organic reactions, including metal-mediated or -catalyzed reactions, condensation reactions, nucleophilic additions, cascade reactions, Diels-Alder reactions, oxidations, reductions, halogenation/aminohalogenation, etc. The ball milling technique has also been applied to the synthesis of calixarenes, rotaxanes and cage compounds, asymmetric synthesis as well as the transformation of biologically active compounds.

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Mechanically Activated Solid-State Synthesis of Flavones by High-Speed Ball Milling

Cited by 25 publications

References 27 publications

Nitrogen‐containing flavonoid and their analogs with diverse B‐ring in acetylcholinesterase and butyrylcholinesterase inhibition

Nitrogen‐containing flavonoid and their analogs with diverse B‐ring in acetylcholinesterase and butyrylcholinesterase inhibition

CHAPTER 1. Carbon–Heteroatom Bond Forming Reactions and Heterocycle Synthesis under Ball Milling

Mechanochemical organic synthesis

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