- Synthesis of structurally diverse biflavonoids
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Synthetic biflavonoids are associated with interesting biological activities, yet they remain poorly explored within drug discovery. Recent years have witnessed a growing interest in synthetic approaches that can provide access to structurally novel biflavonoids so that the biological usefulness of this compound class can be more fully investigated. Herein, we report upon the exploration of strategies based around Suzuki-Miyaura cross-coupling and alcohol methylenation for the synthesis of two classes of biflavonoids: (i) rare ‘hybrid’ derivatives containing flavonoid monomers belonging to different subclasses, and (ii) homodimeric compounds in which the two flavonoid monomers are linked by a methylenedioxy group. Application of these strategies enabled the preparation of a structurally diverse collection of novel biflavonoids from readily-available starting materials, thereby facilitating the probing of uncharted regions of biologically interesting chemical space.
- Sum, Tze Jing,Sum, Tze Han,Galloway, Warren R.J.D.,Twigg, David G.,Ciardiello, Joe J.,Spring, David R.
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supporting information
p. 5089 - 5101
(2018/05/23)
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- Divergent and concise total syntheses of dihydrochalcones and 5-deoxyflavones recently isolated from Tacca species and Mimosa diplotricha
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Dihydrochalcones and 5-deoxyflavones are types of compounds possessing various biologically interesting properties. Herein, we report the concise and divergent total syntheses of several naturally occurring dihydrochalcones and 5-deoxyflavones from readily available starting materials. The divergent strategy is based around manipulation of a common chalcone scaffold and features application of Algar-Flynn-Oyamada oxidation and benzoquinone C-H activation methodologies. These are the first reported total syntheses of these biologically interesting compounds and the concise and flexible route should be readily amenable to future analogue generation. Furthermore, this work provides an illustration of the utility of divergent synthesis for the expedient and step-economical preparation of natural product libraries.
- Sum, Tze Han,Sum, Tze Jing,Stokes, Jamie E.,Galloway, Warren R.J.D.,Spring, David R.
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p. 4557 - 4564
(2015/06/08)
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- Design and synthesis of 3,3′-biscoumarin-based c-Met inhibitors
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A library of biscoumarin-based c-Met inhibitors was synthesized, based on optimization of 3,3′-biscoumarin hit 3, which was identified as a non-ATP competitive inhibitor of c-Met from a diverse library of coumarin derivatives. Among these compounds, 38 and 40 not only showed potent enzyme activities with IC50 values of 107 nM and 30 nM, respectively, but also inhibited c-Met phosphorylation in BaF3/TPR-Met and EBC-1 cells. This journal is the Partner Organisations 2014.
- Xu, Jimin,Ai, Jing,Liu, Sheng,Peng, Xia,Yu, Linqian,Geng, Meiyu,Nan, Fajun
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p. 3721 - 3734
(2014/06/09)
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- Synthesis and antiproliferative activity of new polyoxo 2-Benzyl-2,3-dihydrobenzofurans and their related compounds
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A set of new polyoxo 2-benzyl-2,3-dihydrobenzofurans and their related compounds, including 2-benzylbenzofuran-3(2H)-ones and 2-benzylbenzofurans, were designed and synthesized. Their antiproliferative activities were evaluated against human gastric cancer (SGC-7901), human fibrosarcoma (HT-1080) and human oral epidermoid carcinoma (KB) cell lines in vitro. Preliminary results showed that some polyoxo 2-benzyl-2,3-dihydrobenzofurans and their related compounds had significant activity comparable with that of cisplatin. 2013 Bentham Science Publishers.
- Qi, Ping,Jiang, Jianhua,Qi, Huan,Jin, Yinghua,Shen, Qirong,Wu, Yingliang,Song, Hongrui,Zhang, Weige
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p. 886 - 894
(2013/12/04)
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- Metal-free oxidation of aromatic carbon-hydrogen bonds through a reverse-rebound mechanism
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Methods for carbon-hydrogen (C-H) bond oxidation have a fundamental role in synthetic organic chemistry, providing functionality that is required in the final target molecule or facilitating subsequent chemical transformations. Several approaches to oxidizing aliphatic C-H bonds have been described, drastically simplifying the synthesis of complex molecules. However, the selective oxidation of aromatic C-H bonds under mild conditions, especially in the context of substituted arenes with diverse functional groups, remains a challenge. The direct hydroxylation of arenes was initially achieved through the use of strong Bronsted or Lewis acids to mediate electrophilic aromatic substitution reactions with super-stoichiometric equivalents of oxidants, significantly limiting the scope of the reaction. Because the products of these reactions are more reactive than the starting materials, over-oxidation is frequently a competitive process. Transition-metal-catalysed C-H oxidation of arenes with or without directing groups has been developed, improving on the acid-mediated process; however, precious metals are required. Here we demonstrate that phthaloyl peroxide functions as a selective oxidant for the transformation of arenes to phenols under mild conditions. Although the reaction proceeds through a radical mechanism, aromatic C-H bonds are selectively oxidized in preference to activated-H bonds. Notably, a wide array of functional groups are compatible with this reaction, and this method is therefore well suited for late-stage transformations of advanced synthetic intermediates. Quantum mechanical calculations indicate that this transformation proceeds through a novel addition-abstraction mechanism, a kind of 'reverse-rebound' mechanism as distinct from the common oxygen-rebound mechanism observed for metal-oxo oxidants. These calculations also identify the origins of the experimentally observed aryl selectivity.
- Yuan, Changxia,Liang, Yong,Hernandez, Taylor,Berriochoa, Adrian,Houk, Kendall N.,Siegel, Dionicio
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p. 192 - 196
(2013/08/23)
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- A facile demethylation of ortho substituted aryl methyl ethers promoted by AlCl3
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An efficient and practical demethylation of ortho substituted aryl methyl ethers using AlCl3 has been developed. This method gives a high conversion, is simple to operate and is cost-effective. A mechanism involving the complexation of AlCl3 with the OMe and the adjacent electron withdrawing group is proposed. Many functional groups can be tolerated in the demethylation process, and 29 examples gave a demethylated product in a yield of 90-98%.
- Du, Zhen-Ting,Lu, Jing,Yu, Hong-Rui,Xu, Yan,Li, An-Pai
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experimental part
p. 222 - 227
(2010/08/04)
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- Synthesis of 2-styrylchromones as a novel class of antiproliferative agents targeting carcinoma cells
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A series of 2-styrylchromone analogs were synthesized and examined for their antiproliferative effects on a panel of carcinoma cells. Among the tested agents, only 4m exhibited a moderate activity with an IC50 value of 28.9 μM against PC-3 cells which indicates the selectivity of PC-3 cells in response to 2-styrylchromones. In addition, 4q demonstrated the most antiproliferative effect with an IC50 value of 4.9 μM against HeLa cells. Flow cytometric analysis and DAPI staining revealed that HeLa cells exposed to 4q as low as 5 μM induced cell death through sub-G1 arrest and DNA fragmentation. Furthermore, CoMFA analysis of tested 2-styrylchromones resulted in a q2 of 0.459 to generate a 3D-QSAR model on BT483 cell line. Together, these results suggest a potential structural optimization and pharmacological study of 2-styrylchromones.
- Shaw, Arthur Y.,Chang, Chun-Yi,Liau, Hao-Han,Lu, Pei-Jung,Chen, Hui-Ling,Yang, Chia-Ning,Li, Hao-Yi
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experimental part
p. 2552 - 2562
(2009/09/30)
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- Selective demethylation and debenzylation of aryl ethers by magnesium iodide under solvent-free conditions and its application to the total synthesis of natural products
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An efficient selective demethylation and debenzylation method for aryl methyl/benzyl ethers using magnesium iodide under solvent-free conditions has been developed and applied to the synthesis of natural flavone and biphenyl glycosides. A variety of functional groups including glycoside were tolerated under the reaction conditions. Experimental results indicated that the removal of an O-benzyl group was easier than that of an O-methyl group, regardless of wherever they were meta or para to the carbonyl. Thus selective debenzylation can be achieved for substrates bearing both benzyloxy and methoxy groups.
- Bao, Kai,Fan, Aixue,Dai, Yi,Zhang, Liang,Zhang, Weige,Cheng, Maosheng,Yao, Xinsheng
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scheme or table
p. 5084 - 5090
(2010/04/03)
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- Synthesis and antiproliferative in-vitro activity of natural flavans and related compounds
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The total synthesis of natural flavan racemates (±) 1, (±) 2 and natural flavones 3, 4 had thus been achieved. A straightforward synthetic procedure of flavans via the Pd-C catalyzed hydrogenation/hydrogenolysis of corresponding flavones was developed. Furthermore, the antiproliferative activities of racemic flavans (±) 1, (±) 2, flavones 3, 4, and five synthetic intermediates toward human SGC-7901, BEL-7402, HeLa, and HL-60 cell lines in vitro were evaluated by MTT assay, and the racemic flavans (±) 1 were found to have significant antiproliferative activity against all four cell lines.
- Zhang, Liang,Zhang, Wei-Ge,Ma, En-Long,Wu, Lan,Bao, Kai,Wang, Xiao-Long,Wang, Yu-Ling,Song, Hong-Rui
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p. 650 - 655
(2008/12/21)
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- FLAVONES
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The present invention relates to flavone compounds and their use in methods of treating or preventing parasitic infections, fungal infections and cell proliferative disorders. The present invention also relates to the use of flavone compounds in methods of controlling pests.
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Page/Page column 18; 49-50
(2008/06/13)
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- First total synthesis of two 5-deoxyflavone derivatives from Albizia odoratissima
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The first total synthesis of two unusual 5-deoxyflavone derivatives from Albizia odoratissima, 7,8-dimethoxy-3′,4′-methylenedioxyflavone 1 and 7,2′,4′-trimethoxy-flavone 2, has been accomplished.
- Gao, Jin-Ming,Lu, Jia-Wen,Zhang, An-Ling,Cheng, Yong-Xian,Watchueng, Jean,Konishi, Yasuo
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p. 163 - 164
(2007/10/03)
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- Total synthesis of heliannone A and (R,S)-heliannone B, two bioactive flavonoids from Helianthus annuus cultivars
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The total synthesis of heliannone A (1) and (R,S)-heliannone B (2), two bioactive flavonoids originally isolated from Helianthus annuus cultivars, is described.
- Rao,Rao,Kishore,Gunasekar
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p. 368 - 369
(2007/10/03)
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- XANTHONOLIGNOIDS FROM KIELMEYERA CORIACEA
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Key Word Index - Kielmeyera coriacea; Guttiferae; synthesis; kielcorin; cis-kielcorin; kielcorin B; xanthonolignoids. The synthesis of kielcorin and the tentative identification of kielcorin B (5-hydroxymethyl-6-guaiacyl-2,3:3',2',4'-methoxyxanthone-1,4-dioxane), isomeric xanthonolignoids of Kielmeyera coriacea are reported.
- De M. Pinto, Madalena M.,Mesquita, Antonio A. L.,Gottlieb, Otto R.
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p. 2045 - 2048
(2007/10/02)
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