65548-55-2Relevant academic research and scientific papers
Convenient synthesis and physiological activities of flavonoids in Coreopsis lanceolata L. petals and their related compounds
Nakabo, Daisuke,Okano, Yuka,Kandori, Naomi,Satahira, Taisei,Kataoka, Naoya,Akamatsu, Junpei,Okada, Yoshiharu
, p. 1 - 25 (2018/07/31)
Chalcones, flavanones, and flavonols, including 8-methoxybutin isolated from Coreopsis lanceolata L. petals, were successfully synthesized with total yields of 2–59% from O-methylpyrogallols using the Horner–Wadsworth–Emmons reaction as a key reaction. Au
Novel synthesised flavone derivatives provide significant insight into the structural features required for enhanced anti-proliferative activity
Ravishankar, Divyashree,Watson, Kimberly A.,Greco, Francesca,Osborn, Helen M. I.
, p. 64544 - 64556 (2016/07/21)
With many cancers showing resistance to current chemotherapies, the search for novel anti-cancer agents is attracting considerable attention. Natural flavonoids have been identified as useful leads in such programmes. However, since an in-depth understanding of the structural requirements for optimum activity is generally lacking, further research is required before the full potential of flavonoids as anti-proliferative agents can be realised. Herein a broad library of 76 methoxy and hydroxy flavones, and their 4-thio analogues, was constructed and their structure-activity relationships for anti-proliferative activity against the breast cancer cell lines MCF-7 (ER +ve), MCF-7/DX (ER +ve, anthracycline resistant) and MDA-MB-231 (ER -ve) were probed. Within this library, 42 compounds were novel, and all compounds were afforded in good yields and >95% purity. The most promising lead compounds, specifically the novel hydroxy 4-thioflavones 15f and 16f, were further evaluated for their anti-proliferative activities against a broader range of cancer cell lines by the National Cancer Institute (NCI), USA and displayed significant growth inhibition profiles (e.g. compound-15f: MCF-7 (GI50 = 0.18 μM), T-47D (GI50 = 0.03 μM) and MDA-MB-468 (GI50 = 0.47 μM) and compound-16f: MCF-7 (GI50 = 1.46 μM), T-47D (GI50 = 1.27 μM) and MDA-MB-231 (GI50 = 1.81 μM)). Overall, 15f and 16f exhibited 7-46 fold greater anti-proliferative potency than the natural flavone chrysin (2d). A systematic structure-activity relationship study against the breast cancer cell lines highlighted that free hydroxyl groups and the B-ring phenyl groups were essential for enhanced anti-proliferative activities. Substitution of the 4-CO functionality with a 4-CS functionality, and incorporation of electron withdrawing groups at C-4′ of the B-ring phenyl, also enhanced activity. Molecular docking and mechanistic studies suggest that the anti-proliferative effects of flavones 15f and 16f are mediated via ER-independent cleavage of PARP and downregulation of GSK-3β for MCF-7 and MCF-7/DX cell lines. For the MDA-MB-231 cell line, restoration of the wild-type p53 DNA binding activity of mutant p53 tumour suppressor gene was indicated.
Substituted benzopyranones as telomerase inhibitors
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, (2008/06/13)
The present invention relates to benzopyranone derivatives, to methods for treating telomerase-modulated diseases, in particular cancers, with said derivatives, to a process for their preparation, to their use as medicaments and to pharmaceutical compositions comprising them.
An efficient conversion of 2'-hydroxychalcones into flavanones: Use of tetra-n-butylammonium iodide
Dhawan, Deepika,Grover, S. K.
, p. 73 - 74 (2007/10/03)
2'-Hydroxychalcones 1 possessing different substitution patterns in rings A and B, have been found to undergo efficient isomerization to the corresponding flavanones 2 when heated in ethanol with hydrochloric acid and tetra-n-butylammonium iodide.
Synthesis and Pharmacological Evaluation of 2'-Hydroxychalcones and Flavones as Inhibitors of Inflammatory Mediators Generation
Ballesteros, J. F.,Sanz, M. J.,Ubeda, A.,Miranda, M. A.,Iborra, S.,et al.
, p. 2794 - 2797 (2007/10/03)
2'-Hydroxy-3,4-dimethoxy-3',4'-dimethylchalcone (3a), 2'-hydroxy-3',4',3,4-tetramethoxychalcone (3b), and their corresponding flavones, 3',4'-dimethoxy-7,8-dimethylflavone (4a) and 3',4',7,8-tetramethoxyflavone (4b), were prepared from 3,4-dimethoxycinnam
