4047-24-9Relevant academic research and scientific papers
Anti‐melanogenic properties of velutin and its analogs?
Choe, Jung-Won,Heo, Hee-Young,Jung, Se-Hui,Kim, Jaehyun,Lee, Kooyeon
, (2021/06/03)
Velutin, one of the flavones contained in natural plants, has various beneficial activities, such as skin whitening, as well as anti‐inflammatory, anti‐allergic, antioxidant, and antimicrobial activities. However, the relationship between the structure of velutin and its anti‐melanogenesis activity is not yet investigated. In this study, we obtained 12 velutin derivatives substituted at C5, C7, C3′, and C4′ of the flavone backbone with hydrogen, hydroxyl, and methoxy functionalities by chemical synthesis, to perform SAR analysis of velutin structural analogues. The SAR study revealed that the substitution of functional groups at C5, C7, C3′, and C4′ of the flavone backbone affects biological activities related to melanin synthesis. The coexistence of hydroxyl and methoxy at the C5 and C7 position is essential for inhibiting tyrosinase activity. However, 1,2‐diol compounds substituted at C3′ and C4′ of flavone backbone induce apoptosis of melanoma cells. Further, substitution at C3′ and C4′ with methoxy or hydrogen is essential for inhibiting melanogenesis. Thus, this study would be helpful for the development of natural‐derived functional materials to regulate melanin synthesis.
New homoisoflavonoid analogues protect cells by regulating autophagy
Gan, Li-She,Zeng, Lin-Wei,Li, Xiang-Rong,Zhou, Chang-Xin,Li, Jie
supporting information, p. 1441 - 1445 (2017/03/08)
As a special group of naturally occurring flavonoids, homoisoflavonoids have been discovered as active components of several traditional Chinese medicines for nourishing heart and mind. In this study, twenty homoisoflavonoid analogues, including different substitution groups on rings A and B, as well as heteroaromatic B ring, were synthesized and evaluated for their cardioprotective and neuroprotective activities. In a H2O2-induced H9c2 cardiomyocytes injury assay, nine homoisoflavonoid analogues showed promising activities in the same level as the positive control, diazoxide. Six cardioprotective compounds with representative structure diversities were then evaluated for their neuroprotective effects on MPP+ induced SH-SY5Y cell injury model. Furthermore, autophagy inducing monodansylcadaverine (MDC) fluorescence staining methods and molecular docking studies indicated the action mechanism of these compounds may involve autophagy regulating via class I PI3K signaling pathway.
NOVEL ANALOGUES OF EPICATECHIN AND RELATED POLYPHENOLS
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Paragraph 0189, (2016/03/05)
The present invention provides novel analogues of epicatechin and related polyphenols, their variously functionalized derivatives, process for preparation of the same, composition comprising these compounds and their method of use.
Anti-proliferative effect of chalcone derivatives through inactivation of NF-κB in human cancer cells
Venkateswararao, Eeda,Sharma, Vinay K.,Yun, Jieun,Kim, Youngsoo,Jung, Sang-Hun
, p. 3386 - 3392 (2014/06/23)
To investigate the anti-proliferative effect of NF-κB inhibitor, a series of analogs of (E)-1-(2-hydroxy-6-(isopentyloxy)phenyl)-3-(4- hydroxyphenyl)prop-2-en-1-one (5a) were prepared and evaluated for their NF-κB inhibition and anti-proliferative activity against various human cancer cell lines. Compounds (E)-1-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3- (4-hydroxyphenyl)prop-2-en-1-one (5e) and (E)-4-(3-(2-(3,3-dimethylbutoxy)-6- hydroxyphenyl)-3-oxoprop-1-enyl)benzenesulfonamide (5p) showed good NF-κB inhibition as well as potent anti-proliferative activity. SAR studies showed that all the compounds with potent or moderate NF-κB inhibition displayed good anti-proliferative activity. All the analogs (5b-r) maintained a good correlation between their NF-κB inhibition and anti-proliferative activity though the extent is not directly proportional to each other.
Development of flavonoid-based inverse agonists of the key signaling receptor US28 of human cytomegalovirus
Kralj, Ana,Nguyen, Mai-Thao,Tschammer, Nuska,Ocampo, Nicolette,Gesiotto, Quinto,Heinrich, Markus R.,Phanstiel, Otto
, p. 5019 - 5032 (2013/07/26)
A series of 31 chalcone- and flavonoid-based derivatives were synthesized in good overall yields and screened for their inverse agonist activity on the US28 receptor of human cytomegalovirus (HCMV). With one exception (e.g., 2-(5-bromo-2-methoxyphenyl)-3-hydroxy-4H-chromen-4-one), halogen-substituted flavonoids were typically more potent inverse agonists than their related hydro derivatives. While toxicity could be used to partially explain the inverse agonist activity of some members of the series, 5-(benzyloxy)-2-(5-bromo-2- methoxyphenyl)-4H-chromen-4-one (11b) acted on the US28 receptor as a nontoxic, inverse agonist. The full inverse agonism (efficacy, -89%) and potency (EC 50 = 3.5 μM) observed with flavonoid 11b is especially important as it provides both a new tool to study US28 signaling and a potential platform for the future development of HCMV-targeting drugs.
An efficient procedure for the preparation of natural products bearing the 2-(2-phenylethyl)chromone skeleton
Williams, Dwight A.,Smith, Cameron,Zhang, Yan
, p. 4292 - 4295 (2013/07/26)
Several 2-(2-phenylethyl)chromones have been shown to possess neuroprotective activity. However, limited synthetic methods have been disclosed to construct the 2-(2-phenylethyl)chromone skeleton. Herein, we report a straightforward 3-step preparation of f
A one-pot synthesis of aurones from substituted acetophenones and benzaldehydes: A concise synthesis of aureusidin
Zhao, Xiaolong,Liu, Jie,Xie, Zhixiang,Li, Ying
experimental part, p. 2217 - 2224 (2012/09/22)
A one-pot synthesis of aurones from substituted acetophenone and benzaldehyde has been developed on the basis of an improved Algar-Flynn-Oyamada reaction. By using this method, several aurones were prepared in three steps from commercial starting materials. The usefulness of this one-pot strategy was confirmed by a synthesis of aureusidin, an inhibitor of iodothyronine deiodinase, in 41% overall yield. In comparison with a two-step synthesis of this product from the same substrates, the one-pot strategy was more effective, giving a higher yield and requiring fewer and simpler operations. Georg Thieme Verlag Stuttgart New York.
Substituted chromones as highly potent nontoxic inhibitors, specific for the breast cancer resistance protein
Valdameri, Glaucio,Genoux-Bastide, Estelle,Peres, Basile,Gauthier, Charlotte,Guitton, Jér?me,Terreux, Rapha?l,Winnischofer, Sheila M. B.,Rocha, Maria E. M.,Boumendjel, Ahcène,Di Pietro, Attilio
supporting information; experimental part, p. 966 - 970 (2012/03/10)
A series of 13 disubstituted chromones was synthesized. Two types of substituents, on each side of the scaffold, contributed to both the potency of ABCG2 inhibition and the cytotoxicity. The best compound, 5-(4-bromobenzyloxy)- 2-(2-(5-methoxyindolyl)ethy
A SAR study on a series of synthetic lipophilic chalcones as Inhibitor of transcription factor NF-κB
Venkateswararao, Eeda,Sharma, Vinay K.,Lee, Ki-Cheul,Sharma, Niti,Park, Sun-Hong,Kim, Youngsoo,Jung, Sang-Hun
experimental part, p. 379 - 386 (2012/10/08)
To define the structural features responsible for the activity of 2,4-dihydroxy-6-isopentyloxychalcone, a newly established inhibitor of LPS induced NF-κB activation (IC50 = 10 μM), a series of its analogues was prepared and studied for their i
Towards the first inhibitors of trihydroxynaphthalene reductase from Curvularia lunata: Synthesis of artificial substrate, homology modelling and initial screening
Brunskole, Mojca,Stefane, Bogdan,Zorko, Karmen,Anderluh, Marko,Stojan, Jure,Lanisnik Rizner, Tea,Gobec, Stanislav
, p. 5881 - 5889 (2008/12/20)
Trihydroxynaphthalene reductase (3HNR) is an essential enzyme in the biosynthesis of fungal melanin and it represents an emerging target for the development of new fungicides and antimicotics. To promote the discovery of new inhibitors, an improved chemic
