39103-33-8Relevant academic research and scientific papers
Synthesis of Spiro[benzofuran-2,2'-benzo[b]thiophene]-3,3'-diones via PIDA/CuBr-Mediated Spirocyclization
Du, Yunfei,Li, Xuemin,Liang, Huiyuan,Sun, Fengxia,Wang, Donghua,Wang, Xi,Yang, Yaxin O,Zhang, Jingran
, p. 6563 - 6569 (2020/11/16)
A phenyliodine(III) diacetate (PIDA)/CuBr-mediated construction of the novel 3H,3'H-spiro[benzofuran-2,2'-benzo[b]thiophene]-3,3'-dione skeleton was realized from the reaction of (Z)-3-hydroxy-1-(2-hydroxyphenyl)-3-(2-halogenphenyl)prop-2-en-1-ones with p
Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma
Byrne, Andrew J.,Bright, Sandra A.,Fayne, Darren,McKeown, James P.,McCabe, Thomas,Twamley, Brendan,Williams, Clive,Meegan, Mary J.
, p. 181 - 199 (2018/03/13)
Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.
One-pot synthesis of 3-fluoroflavones: Via 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-diones and selectfluor at room temperature
Wang, Rui,Han, Jie,Li, Chenchen,Zhang, Jie,Liang, Yong,Wang, Tao,Zhang, Zunting
supporting information, p. 2479 - 2488 (2018/04/12)
A concise and efficient one-pot strategy to synthesize 3-fluoroflavones was developed. 1-(2-Hydroxyphenyl)-3-phenylpropane-1,3-diones were fluorinated using selectfluor with a small amount of CH3CN at room temperature, followed by cyclization a
Suppression of PGE2 production via disruption of MAPK phosphorylation by unsymmetrical dicarbonyl curcumin derivatives
Mohd Aluwi, Mohd Fadhlizil Fasihi,Rullah, Kamal,Haque, Md. Areeful,Yamin, Bohari M.,Ahmad, Waqas,Amjad, Muhammad Wahab,Leong, Sze Wei,Fahmizar, Nurul Amira,Jalil, Juriyati,Abas, Faridah,Ismail, Nor Hadiani,Jantan, Ibrahim,Lam, Kok Wai
, p. 3323 - 3335 (2017/10/06)
Curcumin is an important molecule found in turmeric plants and has been reported to exhibit some profound anti-inflammatory activities by interacting with several important molecular targets found in the mitogen-activated protein kinase and NF-κβ pathways. As part of our continuing effort to search for new anti-inflammatory agents with better in vitro and in vivo efficacies, we have synthesized a series of new unsymmetrical dicarbonyl curcumin derivatives and tested their effects on prostaglandin E2 secretion level in interferon-γ/lipopolysaccharide-activated macrophage cells. Among those, five compounds exhibited remarkable suppression on prostaglandin E2 production with IC50 values ranging from 0.87 to 18.41 μM. The most potent compound 17f was found to down-regulate the expression of cyclooxygenase-2 mRNA suggesting that this series of compounds could possibly target the mitogen-activated protein kinase signal transduction pathway. Whilst the compound did not affect the expression of the conventional mitogen-activated protein kinases, the results suggest that it could disrupt the phosphorylation and activation of the proteins particularly the c-Jun N-terminal kinases. Finally, the binding interactions were examined using the molecular docking and dynamics simulation approaches.
A Baker-Venkataraman retro-Claisen cascade delivers a novel alkyl migration process for the synthesis of amides
Ameen, Dana,Snape, Timothy J.
supporting information, p. 1816 - 1819 (2015/03/30)
A simple extension of the carbamoyl Baker-Venkataraman rearrangement has been developed. If residual water in the reaction is not strictly excluded a Baker-Venkataraman retro-Claisen cascade takes place, giving amide products, in which an alkyl group apparently migrates between two functionalities of the substrate.
Synthesis and Fluoride Ion - Triggered Chemiluminescence (CIEEL Mechanism) of Siloxy-Substituted Benzofuran Dioxetanes
Adam, Waldemar,Fell, Rainer,Schulz, Manfred H.
, p. 2227 - 2238 (2007/10/02)
The dioxetanes 2 with tert-butyldimethylsiloxy-substituted aryl groups have been prepared from the corresponding benzofurans by photooxygenation and their fluoride ion-triggered CIEEL chemiluminescence was investigated; facile saponification by fluoride and even phenoxide ions of the aryl esters 4 is held responsible for the low chemiluminescence efficiencies.Keywords: Benzofuran Dioxetanes / CIEEL / Fluoride Ion Triggering / Chemiluminescence
