cas 478-01-3, NOBILETIN | Articles data

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Synthesis of Polymethoxyflavonoids from Hesperidin and Naringin and their Antiproliferative Activity
[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.
Su, Liang,Jin, Zhizhong,Liu, Kexiong,Wang, Qiuan
p. 100 - 105
(2022/03/27)

preparing methods of nobiletin
The present invention provides a process for preparing nobiletin. The present invention relates to a method for preparing nobiletin by using a specific reagent.
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Paragraph 0142-0143; 0175-0177; 0179-0180

(2021/08/24)

Practical Synthesis of Polymethylated Flavones: Nobiletin and Its Desmethyl Derivatives
We present a practical synthesis of the polymethoxylated citrus flavone nobiletin that is suitable for use on a hundred gram scale. Ready availability of this compound and its derivatives will aid detailed chemical-biological investigations of their biological activities, including activation of signaling via the cAMP-dependent protein kinase A/extracellular signal-related protein kinase/cAMP response element-binding protein pathway.
Asakawa, Tomohiro,Sagara, Hiroto,Kanakogi, Masaki,Hiza, Aiki,Tsukaguchi, Yuta,Ogawa, Takahiro,Nakayama, Miho,Ouchi, Hitoshi,Inai, Makoto,Kan, Toshiyuki
p. 595 - 602
(2019/04/01)

Use of flavone and flavanone derivatives in preparation of sedative and hypnotic drugs
Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.
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Page/Page column 48; 49; 50; 52

(2017/07/01)

Synthesis of Citrus polymethoxyflavonoids and their antiproliferative activities on Hela cells
Abstract: A series of polymethoxyflavonoids (3–16) were synthesized through dehydrogenation, O-methylation, glycoside hydrolysis, bromination, microwave-assisted aromatic nucleophilic substitution, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. All the synthetic compounds were test for antiproliferative activities on human cervical carcinoma Hela cell line by the standard CCK-8 assay, the result showed that most of the target compounds exhibited moderate to potent antiproliferative activities on Hela cells comparable with the positive control cis-Platin. Among them, 5-hydroxypolymethoxy flavonoid 13 showed the strongest activity (IC50 0.791 μM). Graphical Abstract: [InlineMediaObject not available: see fulltext.].
Nguyen, Van-Son,Li, Wei,Li, Yue,Wang, Qiuan
p. 1585 - 1592
(2017/06/05)

USE OF FLAVONE AND FLAVANONE DERIVATIVES IN PREPARATION OF SEDATIVE AND HYPNOTIC DRUGS
Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.
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Paragraph 0223; 0239

(2015/07/22)

Synthetic studies of fisetin, myricetin and nobiletin analogs and related probe molecules
We synthesized a series of analogs of fisetin, myricetin and nobiletin, as well as related fluorescein- and biotin-based flavone-probe molecules, on a suitable scale for biological and structure-activity relationship studies.
Hiza, Aiki,Tsukaguchi, Yuta,Ogawa, Takahiro,Inai, Makoto,Asakawa, Tomohiro,Hamashima, Yoshitaka,Kan, Toshiyuki
p. 1371 - 1396
(2016/10/12)

PET imaging of nobiletin based on a practical total synthesis
A practical synthesis of nobiletin, a polymethoxylated citrus flavone, was accomplished by utilizing our novel flavone synthesis. Synthetic nobiletin was labelled by selective demethylation and rapid incorporation of 11C atom. Positron emission tomography images successfully visualized the brain distribution, which may provide therapeutic benefits in the treatment of Alzheimer's disease. The Royal Society of Chemistry.
Asakawa, Tomohiro,Hiza, Aiki,Nakayama, Miho,Inai, Makoto,Oyama, Dai,Koide, Hiroyuki,Shimizu, Kosuke,Wakimoto, Toshiyuki,Harada, Norihiro,Tsukada, Hideo,Oku, Naoto,Kan, Toshiyuki
supporting information; experimental part
p. 2868 - 2870
(2011/04/22)

Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids
The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3′,4′,5,6,7,8- heptamethoxyflavone, quercetin and its derivatives were synthesized.
Chu, Han-Wei,Wu, Huan-Ting,Lee, Yean-Jang
p. 2647 - 2655
(2007/10/03)

Improved, rapid and efficient synthesis of polymethoxyflavones under microwave irradiation and their inhibitory effects on melanogenesis
The microwave-assisted methylation of 2,5-dihydroxy-1,3-dimethoxybenzene with (CH3O)2SO2 for 5 min gave easily 1,2,3,5-tetramethoxybenzene, which was converted into pentamethoxybenzene. The microwave-assisted Friedel-Crafts acylation of pentamethoxybenzene in the presence of In(CF3SO3)3 gave pentamethoxyacetophenone for 15 min under solvent-free conditions in high yield. The microwave-assisted cyclization reaction of the diketones, which were synthesized from the acetophenone via three steps under microwave irradiation, gave the desired polymethoxyflavones for 1.5-3 min in high yields. The polymethoxyflavones showed inhibitory effects on melanogenesis in a human melanoma.
Tsukayama, Masao,Kawamura, Yasuhiko,Ishizuka, Takaaki,Hayashi, Shinji,Torii, Fumihito
p. 2775 - 2784
(2007/10/03)

POLYOXYGENATED FLAVONES FROM AGERATUM CONYZOIDES
Key Word Index - Ageratum conyzoides; Asteraceae; 5,6,7-trimethoxy-3',4'-methylenedioxyflavone; 5,6,7,3'-tetramethoxy-4'-hydroxyflavone; 5,6,7,3',5'-pentamethoxy-4'-hydroxyflavone; polyoxygenated flavones.Twelve polyoxygenated flavones have been isolated from Ageratum conyzoides, three of which are new natural flavones, namely ageconyflavones A (5,6,7-trimethoxy-3',4'-methylenedioxyflavone), B (5,6,7,3'-tetramethoxy-4'-hydroxyflavone) and C (5,6,7,3',5'-pentamethoxy-4'-hydroxyflavone).The other nine compounds were identified as linderoflavone B, eupalestin, nobiletin, 5'-methoxynobiletin, 5,6,7,5'-tetramethoxy-3',4'-methylenedioxyflavone, sinensetin, 5,6,7,3',4',5'-hexamethoxyflavone, 5,6,7,8,3'-pentamethoxy-4'-hydroxyflavone and 5,6,7,8,3',5'-hexamethoxy-4'-hydroxyflavone.
Vyas, Ashok V.,Mulchandani, Newand B.
p. 2625 - 2628
(2007/10/02)

TLC, UV AND ACIDIC TREATMENT IN THE DIFFERENTIATION OF 5,6- AND 5,8-DIHYDROXYFLAVONES, 3-METHOXYFLAVONES AND FLAVONOLS
UV and TLC techniques constitute easy procedures to distinguish between 5,6-dihydroxy-7,8-dimethoxy- and 5,8-dihydroxy-6,7-dimethoxyflavonoids, that are difficult to characterize by NMR and classical UV techniques.The acidic treatment of the original products to obtain Wessely-Moser isomers, useful for comparison purposes, yielded novel demethylated products.UV and MS data of 5,8,4' -trihydroxy-6,7,3'-trimethoxyflavone, 5,6,8,3',4'-pentahydroxy-7-methoxyflavone and 5,6,8,4'-tetrahydroxy-7,3'-dimethoxyflavone are presented for the first time.
Barberan, F.A.T.,Ferreres, F.,Tomas, F.
p. 5733 - 5740
(2007/10/02)

Studies on the constituents of useful plants. V. Multisubstituted flavones in the fruit peel of Citrus reticulata and their examination by gas-liquid chromatography
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Iinuma,Matsuura,Kurogochi,Tanaka
p. 717 - 722
(2007/10/02)