244103-34-2Relevant academic research and scientific papers
Novel β?hydroxy ketones: Synthesis, spectroscopic characterization, molecular docking, and anticancer activity studies
Guzel, Mustafa,Kanturk, Gokhan,Kucuk, Hatice Baspinar,Senturk, Ahmet Mesut,Yerlikaya, Serife,Yildiz, Tulay
, (2021/11/01)
In this study, a series of novel β?hydroxy ketone derivatives 3a-o were designed, synthesized, and evaluated for their anticancer activity. The structure of these compounds were characterized by IR, 1H and 13C NMR, mass spectrometry and elemental analysis methods. All the synthesized compounds were screened for anticancer activity against MCF-7 and U87 cells. Among them, compound 3l was appeared to be the most potent compound on both cancer cells; and IC50 dose was determined as 145 μM for MCF-7 cells and 6,6 μM for U87 cells. DNA ladder and Annexin V apoptotic marker tests were used and as a result, 3l caused the initiation of apoptosis on U87 cells. VDAC protein expression increased dramatically after U87 glioblastoma brain cancer cells were treated with compound 3l Additionally, the molecular modeling of these compounds was studied in FLT3 receptor, Estrogen receptor, and PARP2 receptor for the treatment of Acute Myeloid Leukemia (AML), breast cancer, and Glioblastoma (GBM) respectively. Their binding motifs and drug-like properties were investigated, and the results are highlighted in the discussion. Based on the results, compound 3l may have a potential drug candidate profile that can reverse the drug resistance profile.
Formation and Disproportionation of Xanthenols to Xanthenes and Xanthones and Their Use in Synthesis
Shi, Zeyu,Chen, Si,Xiao, Qiong,Yin, Dali
, p. 3334 - 3343 (2021/02/05)
A facile and versatile strategy employing TiCl4-mediated cyclization followed by a Cannizzaro reaction has been developed for the synthesis of various xanthene derivatives. The reaction proceeded smoothly to afford both xanthenes/xanthones or their sulfur derivatives and tolerated a wide range of electronically diverse substrates. Using this methodology, pranoprofen was synthesized in three steps in 59% overall yield from commercially available starting materials.
Lewis Acid Catalyzed Reductive Cyclization of 2-Aryloxybenzaldehydes and 2-(Arylthio)benzaldehydes to Unsubstituted 9H-Xanthenes and Thioxanthenes in Diisopropyl Ether
Verma, Shashi Kant,Prajapati, Anamika,Saini, Manoj Kumar,Basak, Ashok K.
supporting information, p. 532 - 539 (2020/11/30)
Readily accessible 2-aryloxybenzaldehydes and 2-(arylthio)benzaldehydes undergo a sequence of reactions leading to a wide variety of unsubstituted 9H-xanthenes and thioxanthenes in high yields when heated with a Lewis acid in diisopropyl ether. This reductive cyclization method is compatible with several important functional groups. The method is also applicable for the selective reductive cyclization of the more electron-rich aryl ring of a 2,6-bis(aryloxy)benzaldehyde. The key feature of this transformation is the chemoselective reduction of a transient xanthylium ion in the presence of aldehydic group via intermolecular hydride transfer from diisopropyl ether (solvent). (Figure presented.).
An organocatalytic method for the synthesis of some novel xanthene derivatives by the intramolecular Friedel-Crafts reaction
Yildiz, Tülay,Kü?ük, Hatice Ba?pinar
, p. 16644 - 16649 (2017/03/24)
An efficient organocatalytic method for the synthesis of new substituted 9-arylxanthenes (2a-2u) starting from diarylcarbinol compounds with an arenoxy group (1a-1u) has been developed using the intramolecular Friedel-Crafts reaction. The substrates were
12H-BENZO[A]XANTHEN-12-ONES, COMPOSITIONS CONTAINING, AND USES OF, SAME
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Page/Page column 62, (2017/01/09)
The present invention provides compounds of the following structure, (I), methods of using such compounds, and pharmaceutical compositions containing such compounds. In addition, this invention provides methods for the treatment and/or prevention of disease states mediated by Aryl Hydrocarbon receptor pathways.
Metal-free oxidative coupling: Xanthone formation via direct annulation of 2-aryloxybenzaldehyde using tetrabutylammonium bromide as a promoter in aqueous medium
Rao, Honghua,Ma, Xinyi,Liu, Qianzi,Li, Zhongfeng,Cao, Shengli,Li, Chao-Jun
supporting information, p. 2191 - 2196 (2013/10/01)
A metal-free intramolecular annulation of 2-aryloxybenzaldehydes to xanthones is disclosed, which proceeds through the direct oxidative coupling of an aldehyde C-H bond and aromatic C-H bonds using tetrabutylammonium bromide (TBAB) as a promoter in aqueous medium. This strategy works smoothly in the presence of both electron-donating and electron-withdrawing groups, and displays good tolerance towards catalytically reactive substituents, thus promising further functionalizations of xanthone products.
Wake-promoting agents: Search for next generation modafinil: Part IV
Louvet, Philippe,Schweizer, Dominique,Gourdel, Marie-Edith,Riguet, Eric,Yue, Christoph,Marcy, Val R.,Lin, Yin Guo,Gruner, John,Lesur, Brigitte,Bacon, Edward R.,Chatterjee, Sankar
scheme or table, p. 949 - 951 (2012/10/08)
In search of a next generation molecule to the novel wake promoting agent modafinil, a series of diphenyl ether derived wakefulness enhancing agents (in rat) was developed. From this work, racemic compound 16 was separated into its chiral enantiomers to p
A new synthesis of methyl 7 H-Dibenz[b,g]oxocin-6-carboxylates from Morita-Baylis-Hillman adducts of 2-phenoxybenzaldehydes
Ahn, Sang-Hyun,Jang, Seung Soon,Han, Eun-Gu,Lee, Kee-Jung
experimental part, p. 377 - 386 (2011/04/22)
A new synthetic method for methyl 7H-dibenz[b,g]oxocin-6-carboxylates by Friedel-Crafts reaction of readily available bromides of Morita-Baylis-Hillman adducts with aluminum chloride has been developed. Georg Thieme Verlag Stuttgart New York.
A new synthetic route to unsymmetrical 9-arylxanthenes
Das, Sajal Kumar,Singh, Ritesh,Panda, Gautam
scheme or table, p. 4757 - 4761 (2010/02/28)
A. facile and general three-step synthetic route towards unsymmetrical 9-arylxanthenes was developed. The reaction sequence involves nucleophilic substitution of commercially available 2-fluorobenzaldehydes with arenoxides, Grignard reaction of the resulting 2-arenoxybenzaldehydes with arylmagnesium bromides, followed by FeCl3-catalyzed intramolecular diarylmethylation of the resulting carbinols, This strategy was extended to access symmetrical as well as unsymmetrical 9-arylthioxanthenes.
Iron-catalyzed cascade arene-aldehyde addition/cyclizations for the highly efficient synthesis of xanthenes and its analogous: Observation of a C-C bond cleavage in indole-based triarylmethanes
Li, Hongfeng,Yang, Jingyu,Liu, Yuanhong,Li, Yanzhong
body text, p. 6797 - 6801 (2009/12/30)
(Chemical Equation Presented) An efficient, general, and one-pot procedure for the synthesis of multisubstituted xanthene derivatives through Fe(III)-catalyzed reactions of 2-aryloxybenzaldehydes with electron-rich arenes has been developed. This method offers several advantages such as high selectivities, mild reaction conditions, and easily accessible starting materials. A mechanistic study revealed that a C-C bond cleavage of a triarylmethane intermediate might be involved in the domino process.
