10493-06-8Relevant articles and documents
Structure-activity relationship and pharmacokinetic studies of 3-O-substitutedflavonols as anti-prostate cancer agents
Li, Xiang,Zhang, Changde,Guo, Shanchun,Rajaram, Pravien,Lee, Maizie,Chen, Guanglin,Fong, Ryan,Gonzalez, Aaron,Zhang, Qiang,Zheng, Shilong,Wang, Guangdi,Chen, Qiao-Hong
, p. 978 - 993 (2018)
Thirty-eight 3-O-substituted-3′,4′-dimethoxyflavonols and twenty-five 3-O-substituted-3′,4′,7-trimethoxyflavonols have been synthesized for systematic investigation on the structure-activity relationships of 3-O-substituted-3′,4′-dimethoxyflavonols in thr
Ruthenium(II) carbonyl complexes containing chalconates and triphenylphosphine/arsine
Viswanathamurthi,Muthukumar
, p. 567 - 576 (2011)
A series of new hexa-coordinated ruthenium(II) carbonyl complexes of the type [RuCl(CO)(EPh3)(B)(L1-4)] (4-15) (E = P or As; B = PPh3, AsPh3 or Py; L = 2-hydroxychalcone) were synthesized from the reaction of [RuHCl(CO)(EPh3)2(B)] (1-3) (E = P or As; B = PPh3, AsPh3 or Py) with equimolar chalcone in benzene under reflux. The new complexes have been characterized by analytical and spectroscopic (IR, electronic, 1H, 31P{1H}, and 13C NMR) methods. On the basis of data obtained, an octahedral structure has been assigned for all the complexes. The complexes exhibit catalytic activity for the oxidation of primary and secondary alcohols into their corresponding aldehydes and ketones in the presence of N-methylmorpholine-N-oxide (NMO) as co-oxidant and were also found to be efficient transfer hydrogenation catalysts. The antifungal properties of the ligands and their complexes have also been examined and compared with standard Bavistin. Indian Academy of Sciences.
Isolation and synthesis of flavonols and comparison of their antioxidant activity
Hasan, Aurangzeb,Sadiq,Abbas,Mughal,Khan, Khalid M.,Ali, Muhammad
, p. 995 - 1003 (2010)
Phytochemical investigation of the leaves of Astragalus beckari yielded four flavonol aglycones, namely kaempferol, quercetin, 5-deoxy kaempferol and fisitin. These isolated compounds were then synthesised in the laboratory using the Algar-Flyn-Oyamad reaction. Antioxidant activity of both the isolated and synthesised flavonoids was compared using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay method. The isolated flavonoids were found to be more active.
Natural and Semisynthetic Chalcones as Dual FLT3 and Microtubule Polymerization Inhibitors
Malik, Haleema Sadia,Bilal, Aishah,Ullah, Rahim,Iqbal, Maheen,Khan, Sardraz,Ahmed, Ishtiaq,Krohn, Karsten,Saleem, Rahman Shah Zaib,Hussain, Hidayat,Faisal, Amir
, p. 3111 - 3121 (2020)
Activating mutations in FLT3 receptor tyrosine kinase are found in a third of acute myeloid leukemia (AML) patients and are associated with disease relapse and a poor prognosis. The majority of these mutations are internal tandem duplications (ITDs) in the juxtamembrane domain of FLT3, which have been validated as a therapeutic target. The clinical success of selective inhibitors targeting oncogenic FLT3, however, has been limited due to the acquisition of drug resistance. Herein the identification of a dual FLT3/microtubule polymerization inhibitor, chalcone 4 (2′-allyloxy-4,4′-dimethoxychalcone), is reported through screening of 15 related chalcones for differential antiproliferative activity in leukemia cell lines dependent on FLT3-ITD (MV-4-11) or BCR-ABL (K562) oncogenes and by subsequent screening for mitotic inducers in the HCT116 cell line. Three natural chalcones (1-3) were found to be differentially more potent toward the MV-4-11 (FLT3-ITD) cell line compared to the K562 (BCR-ABL) cell line. Notably, the new semisynthetic chalcone 4, which is a 2′-O-allyl analogue of the natural chalcone 3, was found to be more potent toward the FLT3-ITD+ cell line and inhibited FLT3 signaling in FLT3-dependent cells. An in vitro kinase assay confirmed that chalcone 4 directly inhibited FLT3. Moreover, chalcone 4 induced mitotic arrest in these cells and inhibited tubulin polymerization in both cellular and biochemical assays. Treatment of MV-4-11 cells with this inhibitor for 24 and 48 h resulted in apoptotic cell death. Finally, chalcone 4 was able to overcome TKD mutation-mediated acquired resistance to FLT3 inhibitors in a MOLM-13 cell line expressing FLT3-ITD with the D835Y mutation. Chalcone 4 is, therefore, a promising lead for the discovery of dual-target FLT3 inhibitors.
Hydroxyaurone derivative as well as preparation method and application thereof
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Paragraph 0138; 0141, (2021/07/14)
The invention relates to a hydroxyaurone derivative as well as a preparation method and application thereof. A monomeric compound aurone separated from Kunlun chrysanthemum in Xinjiang is used as a mother nucleus compound, hydroxyl is introduced into auro
A novel one-pot synthesis of flavones
Chang, Meng-Yang,Tsai, Min-Chen,Lin, Chun-Yi
, p. 11655 - 11662 (2021/03/31)
In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.
NOTCH INHIBITORS FOR USE IN THE TREATMENT OF T-CELL ACUTE LYMPHOBLASTIC LEUKEMIA
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Page/Page column 25; 27, (2018/07/29)
Compounds of formula (I) in the capacity of compounds with anti-tumor activity for the treatment of T-cell acute lymphoblastic leukemia (T-ALL).
Reactivity assessment of chalcones by a kinetic thiol assay
Amslinger, Sabine,Al-Rifai, Nafisah,Winter, Katrin,W?rmann, Kilian,Scholz, Rebekka,Baumeister, Paul,Wild, Martin
supporting information, p. 549 - 554 (2013/03/13)
The electrophilic nature of chalcones (1,3-diphenylprop-2-en-1-ones) and many other α,β-unsaturated carbonyl compounds is crucial for their biological activity, which is often based on thiol-mediated regulation processes. To better predict their biological activity a simple screening assay for the assessment of the second-order rate constants (k2) in thia-Michael additions was developed. Hence, a clear structure-activity relationship of 16 differentially decorated hydroxy-alkoxychalcones upon addition of cysteamine could be established. Moreover, amongst other naturally occurring α,β-unsaturated carbonyl compounds k2 values for curcumin and cinnamaldehyde were gained while cinnamic acids or esters gave no or very slow reactions.
Investigation of chalcones as selective inhibitors of the breast cancer resistance protein: Critical role of methoxylation in both inhibition potency and cytotoxicity
Valdameri, Glaucio,Gauthier, Charlotte,Terreux, Rapha?l,Kachadourian, Rémy,Day, Brian J.,Winnischofer, Sheila M. B.,Rocha, Maria E. M.,Frachet, Véronique,Ronot, Xavier,Di Pietro, Attilio,Boumendjel, Ahcène
scheme or table, p. 3193 - 3200 (2012/06/01)
ABCG2 plays a major role in anticancer-drug efflux and related tumor multidrug resistance. Potent and selective ABCG2 inhibitors with low cytotoxicity were investigated among a series of 44 chalcones and analogues (1,3-diarylpropenones), by evaluating their inhibitory effect on the transport of mitoxantrone, a known ABCG2 substrate. Six compounds producing complete inhibition with IC50 values below 0.5 μM and high selectivity for ABCG2 were identified. The number and position of methoxy substituents appeared to be critical for both inhibition and cytotoxicity. The best compounds, with potent inhibition and low toxicity, contained an N-methyl-1-indolyl (compound 38) or a 6′-hydroxyl-2′,4′-dimethoxy-1-phenyl (compound 27) moiety (A-ring) and two methoxy groups at positions 2 and 6 of the 3-phenyl moiety (B-ring). Methoxy substitution contributed to inhibition at positions 3 and 5, but had a negative effect at position 4. Finally, methoxy groups at positions 3, 4, and 5 of the B-ring markedly increased cytotoxicity and, therefore, should be avoided.
Synthesis, spectral characterization and catalytic studies of new ruthenium(II) chalcone thiosemicarbazone complexes
Muthukumar, Manisekar,Viswanathamurthi, Periasamy
experimental part, p. 229 - 240 (2010/12/19)
A series of new hexa-coordinated ruthenium(II) complexes of the type [Ru(CO)(EPh3)(B)(L)] (E = P or As; B = PPh3, AsPh3 or Py; L = chalcone thiosemicarbazone) have been prepared by reacting [RuHCl(CO)(EPh3)2(B)] (E = P or As; B = PPh3, AsPh3 or Py) with chalcone thiosemicarbazones in benzene under reflux. The new complexes have been characterized by analytical and spectroscopic (IR, UV-vis, 1H, 31P and 13C NMR) methods. On the basis of data obtained, an octahedral structure was assigned for all of the complexes. The chalcone thiosemicarbazones behave as dianionic tridentate O, N, S donors and coordinate to ruthenium via the phenolic oxygen of chalcone, the imine nitrogen of thiosemicarbazone and thienol sulfur. The new complexes exhibit catalytic activity for the oxidation of primary and secondary alcohols to their corresponding aldehydes and ketones and they were also found to be efficient catalysts for the transfer hydrogenation of carbonyl compounds. Versita Warsaw and Springer-Verlag Berlin Heidelberg.
