5128-44-9Relevant academic research and scientific papers
Synthesis and antiproliferative activity of novel aminoalkylated flavones
Yan, Lili,Liu, Haoran,Wang, Qiuan,Wang, Gangqiang
, p. 871 - 875 (2017)
(Figure presented.) Naturally occurring 5-hydroxy-4',7-dimethoxyflavone (acacetin-7-O-methyl ether) was synthesized through dehydrogenation, glycoside hydrolysis, and selective O-methylation, using naringin as starting material. Two series of sixteen novel aminoalkylated flavones were synthesized from 5-hydroxy-4',7-dimethoxyflavone. Furthermore, antiproliferative activity of the compounds was evaluated in vitro on a panel of three human cancer cell lines (HeLa, HCC1954, and SK-OV-3) using Cell Counting Kit-8 assay. The result showed that most of the synthetic compounds exhibited moderate to potent antiproliferative activities against the three human cancer cell lines with IC50 values of 6.95–64.50 μΜ.
Syntheses and crystal structures of two apigenin alkylation derivatives
Kou, Li-Qun,Cheng, Xin-Li,Zhang, Zun-Ting
, p. 21 - 25 (2008)
Two apigenin alkylation derivatives, 4′,7-dimethoxyl-5-hydroxyflavone (I) and 4′,7-diethoxyl-5-hydroxyflavone (II), have been synthesized and their crystal structures were determined by 1H NMR and single crystal X-ray diffraction study. (I) is triclinic, space group P-1 with a = 7.120(5) A, b = 7.297(5) A, c = 13.559(10) A, α = 89.313(12)°, β = 86.298(12)°, γ = 83.999(13)° and Z = 2. (II) is monoclinic, space group P 21 /c with a = 16. 309(4) A, b = 7.303(2) A, c = 15.185(4) A, α = 90.00°, β = 115.70(2)°, γ = 90.00° and Z = 4. They have the same flavone skeleton which is composed of a benzopyranone moiety and a phenyl moiety. Molecules of (I) are linked into a two-dimensional network by a combination of C-H...O hydrogen bond and π-π stacking interactions. (II) shows some discrepancies with (I) and the molecules are linked into a column by π-π stacking interaction.
Synthesis of Polymethoxyflavonoids from Hesperidin and Naringin and their Antiproliferative Activity
Su, Liang,Jin, Zhizhong,Liu, Kexiong,Wang, Qiuan
, p. 100 - 105 (2022/03/27)
[Figure not available: see fulltext.] A series of polymethoxyflavonoids were synthesized via cleavage of the glycosidic bond, dehydrogenation, selective methylation, bromination, nucleophilic aromatic substitution, O-prenylation, Claisen–Schmidt aldol condensation, cyclization, and oxidation from very abundant and inexpensive natural flavonoids hesperidin and naringin. The in vitro antiproliferative activity of the synthesized compounds was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2, and SUN-5) by the CellTiter-Glo assay. The results showed that some of synthesized compounds exhibited moderate to high antiproliferative activity. Among them, (2E)-1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-(7-methoxy-1,3-benzodioxol-5-yl)prop-2-en-1-one was revealed to be the most active with IC50 values ranging from 10.35 to 13.89 μM against all four cancer cell lines, the IC50 value (10.35 μM) being below positive control cisplatin (12.36 μM) against HepG-2 cells.
Silenerepin – a New C-Glycosylflavone from Silene repens
Olennikov
, p. 423 - 426 (2020/06/17)
The new C-glycosylflavone silenerepin or 5-hydroxy-7,4′-dimethoxyflavone-6,8-di-C-β-D-glucopyranoside and 20 known flavonoids were isolated from the herb Silene repens Patrin (Caryophyllaceae). Their structures were elucidated using UV, IR, and NMR spectroscopy and mass spectrometry.
Correlation study on methoxylation pattern of flavonoids and their heme-targeted antiplasmodial activity
Boutefnouchet, Sabrina,Bouzidi, Chouaha,Cojean, Sandrine,Figadère, Bruno,Grougnet, Rapha?l,Maciuk, Alexandre,Michel, Sylvie,Ortiz, Sergio,Vásquez-Ocmín, Pedro G.
, (2020/09/16)
A library of 33 polymethoxylated flavones (PMF) was evaluated for heme-binding affinity by biomimetic MS assay and in vitro antiplasmodial activity on two strains of P. falciparum. Stability of heme adducts was discussed using the dissociation voltage at 50% (DV50). No correlation was observed between the methoxylation pattern and the antiparasitic activity, either for the 3D7 chloroquine-sensitive or for the W2 chloroquine-resistant P. falciparum strains. However, in each PMF family an increased DV50 was observed for the derivatives methoxylated in position 5. Measurement of intra-erythrocytic hemozoin formation of selected derivatives was performed and hemozoin concentration was inversely correlated with heme-binding affinity. Kaempferol showed no influence on hemozoin formation, reinforcing the hypothesis that this compound may exert in vitro antiplasmodial activity mostly through other pathways. Pentamethoxyquercetin has simultaneously demonstrated a significant biological activity and a strong interaction with heme, suggesting that inhibition of hemozoin formation is totally or partially responsible for its antiparasitic effect.
Synthesis of Benzopyran-Fused Flavone Derivatives via Microwave-Assisted Intramolecular C-H Activation
Sipos, Zoltán,Kónya, Krisztina
, p. 1610 - 1620 (2018/03/21)
A microwave-assisted intramolecular direct arylation method for the synthesis of benzopyran-fused flavone derivatives containing natural flavone backbones is described. Different polyalkoxy flavones were synthesized and functionalized with 2-bromobenzyl bromide. The resulting compounds were subjected to palladium-catalyzed intramolecular direct arylation reactions supported by microwave irradiation to produce fused tetracyclic flavones. In the case of the 7-substituted chrysin derivative, the regioselectivity of the coupling was also examined.
Discovery of potent and selective acetylcholinesterase (AChE) inhibitors: acacetin 7-O-methyl ether Mannich base derivatives synthesised from easy access natural product naringin
Liu, Hao-ran,Men, Xue,Gao, Xiao-hui,Liu, Lin-bo,Fan, Hao-qun,Xia, Xin-hua,Wang, Qiu-an
, p. 743 - 747 (2017/10/06)
Naringin, as a component universal existing in the peel of some fruits or medicinal plants, was usually selected as?the material to synthesise bioactive derivates since it was easy to gain with low cost. In present investigation, eight new acacetin-7-O-methyl ether Mannich base derivatives (1–8) were synthesised from naringin. The bioactivity evaluation revealed that most of them exhibited moderate or potent acetylcholinesterase (AChE) inhibitory activity. Among them, compound 7 (IC50 for AChE?=?0.82?±?0.08?μmol?L?1, IC50 for BuChE?=?46.30?±?3.26?μmol?L?1) showed a potent activity and high selectivity compared with the positive control Rivastigmine (IC50 for AChE?=?10.54?±?0.86?μmol?L?1, IC50 for BuChE?=?0.26?±?0.08?μmol?L?1). The kinetic study suggested that compound 7 bind to AChE with mix-type inhibitory profile. Molecular docking study revealed that compound 7 could combine both catalytic active site (CAS) and peripheral active site (PAS) of AChE with four points (Trp84, Trp279, Tyr70 and Phe330), while it could bind with BuChE via only His 20.
Encoding matter with regiospecific 12C/13C isotopic labels
La Clair, James J.
, p. 2611 - 2614 (2018/03/21)
Society suffers due to an inability to regulate matter. This study presents a practical tool for the encryption of materials by adjusting the levels of 13C at regiospecific atoms within a molecule to generate a stable-isotopically encoded signature. This system is demonstrated by securing a document by adapting natural product chemistry as an encryption device. This approach delivers a complex signal that would be difficult to intercept due to the need for access to extraction protocols, sophisticated NMR instrumentation and a vital level of prior knowledge. Overall, this discovery offers an important tool to monitor and track valuable entities on our planet.
Total synthesis of agalloside, isolated from: Aquilaria agallocha, by the 5-O-glycosylation of flavan
Arai, Midori A.,Yamaguchi, Yumi,Ishibashi, Masami
, p. 5025 - 5032 (2017/07/10)
Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic strategy holds promise for use in the synthesis of 5-O-glycosylated flavonoids. The synthesized agalloside (1) accelerated neural stem cell differentiation, which is a result comparable to that for the naturally occurring compound 1.
Synthesis and Antiproliferative Activity of Thioxoflavones Mannich Base Derivatives
Li, Wei,Li, Xueli,Liu, Manhui,Wang, Qiuan
, (2017/07/11)
Two series of 12 novel thioxoflavones Mannich base derivatives 5a–f and 6a–f were synthesized via Mannich reaction of 4′,7-dimethoxy-5-hydroxyflavothione (3) or 3′,4′,7-trimethoxy-5-hydroxyflavothione (4) with appropriate aliphatic amines or alicyclic amines and formaldehyde. Thioxoflavones 3 and 4 were prepared from 4′,7-dimethoxy-5-hydroxyflavone (1) and 3′,4′,7-trimethoxy-5-hydroxyflavone (2) with Lawesson's reagent, respectively. Their antiproliferative activities in vitro were evaluated on a panel of three human cell lines (HeLa, HCC1954, and SK-OV-3) by CCK-8 assay. The results showed that most of the thioxoflavones and their Mannich base derivatives exhibited potential antiproliferative activities on the tested cancer cell lines, with IC50 values ranging from 9.16 to 55.50 μM. In particular, thioxoflavone 4 and the thioxoflavone Mannich base derivatives 5a and 5d showed the best antiproliferative activity on all three human cancer cell lines; they are promising candidates worthy of further development. The structures of all synthesized compounds were confirmed by 1H NMR, 13C NMR, IR, and MS techniques.
