20979-50-4Relevant articles and documents
Formation of the unexpected 3-alkylated flavonoids in the alkylation of B-ring substituted 5,7-dihydroxy flavones
Wang, Cai-Ling,Zheng, Xing,Meng, Wei-Dong,Li, Hong-Qi,Qing, Feng-Ling
, p. 5399 - 5402 (2005)
Treatment of B-ring substituted 5,7-dihydroxy flavones with alkyl halides in the presence of potassium carbonate gave unexpected 3-alkylated flavonoids. Related experiments were carried out to explain the formation of 3-alkylated flavonoids and a ring opening followed by alkylation and ring closure mechanism was proposed.
Microwave assisted efficient synthesis of flavone using ZnO nanoparticles as promoter under solvent-free conditions
Unde, Pradip J.,Thorat, Nitin M.,Patil, Limbraj R.
, p. 1133 - 1136 (2019/04/05)
A simple and highly efficient protocol for synthesis of flavones from 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones in presence of ZnO nanoparticles as a promoter in thermal as well as microwave irradiation under solvent-free conditions have been demonstrated. The catalyst is inexpensive, stable, can be easily recycled/reused for several cycles with consistent activity and observed almost same yield confirming the stability of the catalyst. It is believed that the present approach will become an alternative route for the conventional reactions. Because in this protocol, yield is quite high, short reaction time, simple work up, catalyst can be recycled as well as it is free of any hazardous by-products formation during workup.
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.
L-ascorbic acid: A green and competent promoter for solvent-free synthesis of flavones and coumarins under conventional as well as microwave heating
Dengale, Rohit Arvind,Thorat, Nitin Madhu,Thopate, Shankar Ramchandra
, p. 734 - 741 (2017/02/05)
Background: An expeditious approach has been developed for the synthesis of two distinct classes of benzopyrones viz. flavones and coumarins under solvent-free conditions. L-Ascorbic acid was found to be an effective promoter under microwave irradiation and conventional heating. Various benzo-α-pyrones and benzo-γ-pyrones were synthesized with overall good yields. The present protocol is highly facile and needs no column chromatography for purification and therefore it would serve as an effective and compatible method under both microwave irradiation and conventional heating. Results: The catalytic ability of L-ascorbic acid was investigated for the synthesis of flavones and coumarins. For this purpose, cyclodehydration of 1-(2-hydroxyphenyl)-3-aryl-1,3-propanedione and Pechmann coumarin synthesis, reactions were selected. And accordingly, it was observed that one mole of L-ascorbic acid was necessary for the completion of reaction. In all the cases, the desired flavones were smoothly generated with good to excellent yields; indicating its excellent tolerance for various functional groups. However, electron donating groups favors coumarin synthesis under these conditions. All the reaction mixtures were carefully analyzed and NMR indicates high conversions and lack of side products. Conclusion: We have developed L-ascorbic acid-promoted, solvent-free and simple method for the synthesis of benzo-α-pyrones and benzo-γ-pyrone under microwave irradiation as well as conventional heating in good to excellent yields. The notable advantages of this method are solvent-free conditions, inexpensive and efficient eco-friendly promoter, and shorter reaction time and can be carried out under air. This methodology is highly facile and requires no column chromatography for purification. The resulting flavones and coumarins are versatile building blocks in the construction of heterocyclic architectures, dominant in natural products. Further studies of exploiting the efficiency of L-ascorbic acid as a promoter in synthesis of various heterocyclic compounds are in progress.
Inhibitory effect of flavonoids on human glutaminyl cyclase
Li, Manman,Dong, Yao,Yu, Xi,Zou, Yongdong,Zheng, Yizhi,Bu, Xianzhang,Quan, Junmin,He, Zhendan,Wu, Haiqiang
, p. 2280 - 2286 (2016/04/26)
Glutaminyl cyclase (QC) plays an important role in the pathogenesis of Alzheimer's disease (AD) and can be a potential target for the development of novel anti-AD agents. However, the study of QC inhibitors are still less. Here, phenol-4′ (R1-), C5-OH (R2-) and C7-OH (R3-) modified apigenin derivatives were synthesized as a new class of human QC (hQC) inhibitors. The efficacy investigation of these compounds was performed by spectrophotometric assessment and the structure-activity relationship (SAR) was evaluated. Molecular docking was also carried out to analyze the binding mode of the synthesized flavonoid to the active site of hQC.
Ammonium acetate promoted rapid and efficient synthesis of γ-Benzopyranones and 3,4-dihydropyrimidin-2(1H)-ones/thiones under solventfree conditions: A parallel scrutiny of microwave irradiation versus conventional heating
Thorat, Nitin M.,Dengale, Rohit A.,Thopate, Shankar R.,Rohokale, Sandeep V.
, p. 574 - 583 (2015/10/05)
Simple and highly efficient approach for the synthesis of γ-Benzopyranones and 3,4-Dihydropyrimidin-2(1H)-ones/thiones using ammonium acetate as a promoter under thermal as well as microwave irradiation using solvent-free conditions has been demonstrated.
An efficient and green synthesis of flavones using natural organic acids as promoter under solvent-free condition
Thorat, Nitin M.,Kote, Santosh R.,Thopate, Shankar R.
, p. 601 - 605 (2014/07/21)
An efficient and eco-friendly synthesis of flavones, promoted by naturally occurring acids, via cyclodehydration of 1-(2-hydroxyphenyl)-3-aryl-1,3- propanediones using conventional and microwave heating under solvent-free condition is described.
Pyrrolidine and iodine catalyzed domino aldol-Michael-dehydrogenative synthesis of flavones
Naik, Mayuri M.,Tilve, Santosh G.,Kamat, Vijayendra P.
, p. 3340 - 3343 (2014/06/09)
A one pot synthesis of flavones is established from 2′- hydroxyacetophenones and substituted aromatic aldehydes. The method uses domino aldol-Michael-oxidation reaction catalyzed by pyrrolidine as a base and iodine as an oxidant in dimethyl sulfoxide.
Synthesis of novel 4,6-diaryl-2-aminopyrimidines as potential antiplasmodial agents
Giridhar, Rajani,Tamboli, Riyaj S.,Prajapati, Dhaval G.,Soni, Sanket,Gupta, Sarita,Yadav
, p. 3309 - 3315 (2013/07/27)
A novel series of 4,6-diaryl-2-aminopyrimidines 8a-o has been synthesized and evaluated for in vitro antiplasmodial activity against Plasmodium falciparum. Out of the 15 compounds synthesized and tested, 6 compounds have shown IC50 values in the range of 1.61-9.53 μg/mL. These compounds are several times more potent than chloroquine and quinine, the two standard drugs used for the purpose of comparison.
Cyclization of 2'-hydroxychalcones to flavones using ammonium iodide as an iodine source - An eco-friendly approach
Kulkarni, Pramod S.,Kondhare, Dasharath D.,Varala, Ravi,Zubaidha, Pudukulathan K.
, p. 909 - 916 (2013/08/23)
Ammonium iodide on exposure to air decomposes to ammonia and iodine. The in situ generated iodine was used for the cyclization of 2'-hydroxychalcones to the corresponding flavones under solvent-free conditions in good to excellent yields. This method could serve as an attractive alternative to the existing methods for synthesis of flavones and the use of toxic molecular iodine is avoided. Copyright
