- N-Benzylation of 6-aminoflavone by reductive amination and efficient access to some novel anticancer agents via topoisomerase II inhibition
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Series of novel N-benzyl derivatives of 6-aminoflavone (9a–n) were synthesized and evaluated for anticancer and topoisomerase II enzyme inhibition activity. All the synthesized compounds were screened for in vitro anticancer activity against human breast cancer cell line (MCF-7) and human lung cancer cell line (A-549). Among the synthesized compounds, 9f and 9g were found to be the most potent anticancer agents against human breast cancer cell line (MCF-7) with IC50 values of 9.35?μM and 9.58?μM, respectively. Compounds 9b, 9c and 9n exhibited promising anticancer activity against human lung cancer cell line (A-549) with 43.71%, 46.48% and 44.26% inhibition at the highest concentration of 10?μM, respectively. Compounds 9c, 9f and 9g have ability to inhibit the topoisomerase II enzyme. Compound 9f showed most potent topoisomerase II enzyme inhibition activity with IC50 value of 12.11?μM. Further, these compounds have a high potential to be developed as a promising topoisomerase II inhibitors.
- Thorat, Nitin M.,Sarkate, Aniket P.,Lokwani, Deepak K.,Tiwari, Shailee V.,Azad, Rajaram,Thopate, Shankar R.
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p. 937 - 948
(2020/04/15)
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- Discovery of Novel Dual-Target Inhibitor of Bromodomain-Containing Protein 4/Casein Kinase 2 Inducing Apoptosis and Autophagy-Associated Cell Death for Triple-Negative Breast Cancer Therapy
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Bromodomain-containing protein 4 (BRD4) is an attractive epigenetic target in human cancers. Inhibiting the phosphorylation of BRD4 by casein kinase 2 (CK2) is a potential strategy to overcome drug resistance in cancer therapy. The present study describes the synthesis of multiple BRD4–CK2 dual inhibitors based on rational drug design, structure–activity relationship, and in vitro and in vivo evaluations, and 44e was identified to possess potent and balanced activities against BRD4 (IC50 = 180 nM) and CK2 (IC50 = 230 nM). In vitro experiments show that 44e could inhibit the proliferation and induce apoptosis and autophagy-associated cell death of MDA-MB-231 and MDA-MB-468 cells. In two in vivo xenograft mouse models, 44e displays potent anticancer activity without obvious toxicities. Taken together, we successfully synthesized the first highly effective BRD4–CK2 dual inhibitor, which is expected to be an attractive therapeutic strategy for triple-negative breast cancer (TNBC).
- Chen, Juncheng,Chiang, Cheng-Ming,He, Gu,Liu, Bo,Liu, Jie,Ouyang, Liang,Tang, Pan,Wang, Guan,Yang, Chengcan,Ye, Tinghong,Zhang, Jifa,Zhang, Jin,Zou, Ling
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p. 18025 - 18053
(2022/01/03)
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- Rh(III)-Catalyzed Aldehydic C?H Functionalization Reaction between Salicylaldehydes and Sulfoxonium Ylides
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A novel aldehydic C?H functionalization reaction between salicylaldehydes and sulfoxonium ylides has been developed under rhodium(III) catalysis, affording coupling products in moderate to good yields. A plausible mechanism involving aldehydic C(sp2)?H activation by rhodium(III) and rhodium(III) catalyzed carbene insertion is also proposed. It was also found that the aldehydic C?H functionalization followed by dehydrative cyclization was able to produce flavonoids in one-pot. (Figure presented.).
- Xu, Guo-Dong,Huang, Kenneth L.,Huang, Zhi-Zhen
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supporting information
p. 3318 - 3323
(2019/06/25)
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- Transition-Metal-Free Photoinduced Intramolecular Annulation of 2,3-Di(hetero)arylchromen-4-one
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An efficient transition-metal-free photoinduced intracyclization of 4H-chromen-4-ones in EtOH-H2O (7:1, v/v) at ambient temperature for the construction of complicated fused-ring heteroaromatics is established. The reaction proceeds smoothly without requiring any catalysts/additives.
- Han, Jie,Wang, Tao,Liang, Yong,Li, Ying,Li, Chenchen,Wang, Rui,Feng, Siqi,Zhang, Zunting
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supporting information
p. 3552 - 3555
(2017/07/17)
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- Mild and efficient organocatalytic method for the synthesis of flavones
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A convenient and efficient organocatalytic procedure for the selective cyclization of 1,3-diketones to give aromatic substituted 4H-chromen-4-ones under mild reaction conditions using N-triflyl phosphoramide is described. Application of the described conditions is presented in a formal synthesis of (S)-flavanone.
- Stanek, Filip,Stodulski, Maciej
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supporting information
p. 3841 - 3843
(2016/08/02)
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- Convenient one-pot synthesis of chromone derivatives and their antifungal and antibacterial evaluation
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A one-pot method for the synthesis of chromone derivatives from the reaction of 2-hydroxyacetophenones with aliphatic or aromatic acid chlorides is reported. Esterification and Baker-Venkataraman rearrangement were promoted by t-BuOK, which was followed directly by acid-catalyzed cyclization in one pot. Some of 2-cyclohexyl- and 2-cyclohexylmethyl-substituted chromones displayed activity against plant pathogenic fungal strains. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Ghani, Sherif B. Abdel,Mugisha, Patrick J.,Wilcox, Juliet C.,Gado, Emad A. M.,Medu, Erere O.,Lamb, Andrew J.,Brown, Richard C. D.
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p. 1549 - 1556
(2013/05/22)
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- Microwave-assisted synthesis and antimicrobial activities of flavonoid derivatives
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Eleven flavonoid derivatives were synthesised using a modified Baker-Venkataraman rearrangement, and subsequent microwave-assisted closure of the heterocyclic ring. All of the synthetic compounds displayed antifungal activity against Aspergillus niger and
- Abdel Ghani, Sherif B.,Weaver, Louise,Zidan, Zidan H.,Ali, Hussein M.,Keevil, C. William,Brown, Richard C.D.
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p. 518 - 522
(2008/09/17)
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- New synthesis of 3-bromoflavones via bromination of 1-(2-hydroxyphenyl)-3- arylpropane-1,3-dione by CuBr2, and conversion into 3-aminoflavones
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A new synthesis of 3-bromoflavones from 1-(2-hydroxyphenyl)-3-arylpropane- 1,3-dione using CuBr2 is described. The usefulness of 3-bromoflavone as a precursor of 3-aminoflavone is also described. Copyright
- Miyake, Hideyoshi,Nishino, Shouko,Nishimura, Akinori,Sasaki, Mitsura
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p. 522 - 523
(2008/02/10)
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- Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor
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A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands.
- Marder, Mariel,Zinczuk, Juan,Colombo, Maria I.,Wasowski, Cristina,Viola, Haydee,Wolfman, Claudia,Medina, Jorge H.,Ruveda, Edmundo A.,Paladini, Alejandro C.
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p. 2003 - 2008
(2007/10/03)
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