4142-51-2Relevant articles and documents
Synthesis and anticancer potential of novel xanthone derivatives with 3,6-substituted chains
Liu, Chaomei,Zhang, Mei,Zhang, Zhenhuan,Zhang, Steven B.,Yang, Shanmin,Zhang, Amy,Yin, Liangjie,Swarts, Steven,Vidyasagar, Sadasivan,Zhang, Lurong,Okunieff, Paul
, p. 4263 - 4271 (2016/08/23)
In an effort to develop new drug candidates with enhanced anticancer activity, our team synthesized and assessed the cytotoxicity of a series of novel xanthone derivatives with two longer 3,6-disubstituted amine carbonyl methoxy side chains on either benzene ring in selected human cancer cell lines. An MTT assay revealed that a set of compounds with lower IC50values than the positive control, 5-FU, exhibited greater anticancer effects. The most potent derivative (XD8) exhibited anticancer activity in MDA-MB-231, PC-3, A549, AsPC-1, and HCT116 cells lines with IC50values of 8.06, 6.18, 4.59, 4.76, and 6.09?μM, respectively. Cell cycle analysis and apoptosis activation suggested that the mechanism of action of these derivatives includes cell cycle regulation and apoptosis induction.
Friedel-crafts-type alkylation with bromodifluoro(phenylsulfanyl)methane through α-fluorocarbocations: Syntheses of thioesters, benzophenones and xanthones
Kuhakarn, Chutima,Surapanich, Nakin,Kamtonwong, Siriporn,Pohmakotr, Manat,Reutrakul, Vichai
supporting information; experimental part, p. 5911 - 5918 (2011/12/05)
Bromodifluoro(phenylsulfanyl)methane undergoes a Friedel-Crafts-type alkylation, through α-fluorocarbocations, with activated aromatic compounds yielding thioesters and/or benzophenones. The methodology has been applied to the synthesis of naturally occurring xanthone derivatives.
Antioxidant xanthone derivatives induce cell cycle arrest and apoptosis and enhance cell death induced by cisplatin in NTUB1 cells associated with ROS
Cheng, Jen-Hao,Huang, A-Mei,Hour, Tzyh-Chyuan,Yang, Shyh-Chyun,Pu, Yeong-Shiau,Lin, Chun-Nan
, p. 1222 - 1231 (2011/04/22)
In an effort to develop novel antioxidant as anticancer agents, a series of xanthones were prepared. In vitro screening, the synthetic xanthones revealed significant inhibitory effects on xanthine oxidase and ABTS radical-cation scavenging activity. The selective compounds 2 and 8 induced an accumulation of NTUB1 cells in the G1 phase arrest and cellular apoptosis by the increase of ROS level. The combination of cisplatin and 2 significantly enhanced the cell death in NTUB1 cells. Compounds 2 and 8 did not show cytotoxic activity in selected concentrations against SV-HUC1 cells. The present results suggested that antioxidants 2 and 8 may be used as anticancer agent for enhancing the therapeutic efficacy of anticancer agents and to reduce their side effect.
γ-Pyrone compounds. IV: Synthesis and antiplatelet effects of mono- and dioxygenated xanthones and xanthonoxypropanolamine
Lin,Liou,Ko,Teng
, p. 11 - 16 (2007/10/02)
Xanthodilol, mono- and dioxygenated xanthones, and 1,3-, 2,3-, 3,4-, 3,5- , 1,6-, 2,6-, and 3,6-dioxygenated xanthones were synthesized from benzophenone precursors by Friedel-Crafts acylation and subsequent base- catalyzed cyclization to eliminate methanol. 3-Hydroxyxanthone, xanthodilol, 2,3-dihydroxyxanthone diacetate, and 3,4-dihydroxyxanthone and its diacetate showed potent antiplatelet effects on arachidonate- and collagen-induced aggregation. 3,5-Dihydroxyxanthone and its diacetate, 1,6-dimethoxyxanthone, and 3,6-dihydroxyxanthone and its diacetate showed potent antiplatelet effects on arachidonate-induced aggregation.
Selective Dealkylation of Methoxyanthraquinones via Difluoro1,O9>boron Chelates: Synthesis of Hydroxymethoxyanthraquinones
Preston, Peter N.,Winwick, Thomas,Morley, John O.
, p. 1439 - 1441 (2007/10/02)
1,8-, 1,5- 1,2-, and 1,4-Dimethoxyanthraquinones have been treated with boron trifluoride-diethyl ether to give difluoro(anthraquinonato)boron chelates (1a-d) respectively. 1,4,5-Trimethoxyanthraquinone was similarly converted separately in benzene and toluene into the mono- (2) and bis-difluoroboron(3)-chelates respectively, and 2,2',4,4'-tetramethoxybenzophenone was converted by BF3*Et2O in toluene into the boron adduct (4).Treatment of these derivatives, (1a-d) and (2)-(4), with methanol gave the following uncomplexed derivatives in good yield respectively: 1-hydroxy-8-methoxyanthraquinone, 1-hydroxy-5-methoxyanthraquinone, 1-hydroxy-2-methoxyanthraquinone, 1-hydroxy-4-methoxyanthraquinone, 4-hydroxy-1,5-dimethoxyanthraquinone, 1,4-dihydroxy-5-methoxyanthraquinone, and 2-hydroxy-2',4,4'-trimethoxybenzophenone.
Selective Demethylation of Di- and Tri-methoxyanthraquinones via Aryloxydifluoroboron Chelates. Synthesis of 4-Hydroxy-1,5-dimethoxyanthraquinone and 1,4-Dihydroxy-5-methoxyanthraquinone
Preston, Peter N.,Winwick, Thomas,Morley, John O.
, p. 89 - 90 (2007/10/02)
Methoxyanthraquinone derivatives react with boron trifluoride-diethyl ether to give mono- and bis-difluoroboron chelates which, in methanol, are converted into hydroxyanthraquinones; an extension of this method is described for the synthesis of 2-hydroxy-2',4,4'-trimethoxybenzophenone.
Intramolecular Oxidative Cyclization Reactions of Trivalent Phosphorus and Carbonyl Functions
Harper, S. D.,Arguengo, Anthony J.
, p. 2497 - 2501 (2007/10/02)
Phosphonous diesters derived from the reaction of phenylphosphonous dichloride with 2-ketophenols readily undergo head-to-tail intramolecular cyclization in cases where the carbonyl function is an aldehyde, trifluoromethylacetophenone, or diaryl ketone.A
