cas 2306-27-6, SINENSETIN | Articles data

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5,6-DIMETHOXY-7,3',4',-TRIHYDROXYFLAVONE FROM ANISOMELES OVATA
5,6-Dimethoxy-7,3',4'-trihydroxyflavone was isolated from the aerial parts of Anisomeles ovata and characterized by both physical and chemical methods.Key Word Index - Anisomeles ovata; Labiatae; flavone; 5,6-dimethoxy-7,3',4'-trihydroxyflavone.
Rao, L. Jagan Mohan,Kumari, G. N. Krishna,Rao, N. S. Prakasa
p. 1522
(1983)
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Morita et al.
p. 421,423
(1973)
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Synthesis and anti-proliferative activities of 5,6,7-trimethoxyflavones and their derivatives
A series of 5,6,7-trimethoxyflavones 1a-1g and their derivatives 2a-2g, 3a-3d, 4 and 5, including the natural products 5,6,7-trimethoxy-4’-hydroxyflavone (1a), 5,6,7,3’,4’ -pentamethoxyflavone (sinensetin, 1 b), 5,6,7-trimethoxy-3’,4’-methyl enedioxy flavone (1c), 5,6,7,3’-tetramethoxy-4,5’-methylenedioxyflavone (1e), 5,6,7, 3’,4’,5’-hextamethoxyflavone (1 g), 5-hydroxy-3,4,2’,3’,4’-pentamethoxy chal-cone (2 b), 5,4’-dihydroxy-6,7-dimethoxy flavone (cirsimaritin, 3a) and 5-hydroxy-6,7,3’, 4’-tetramethoxyflavone (5-demethylsinensetin, 3 b), 3,5,6,7,3’,4’-hexamethoxyflavone (3-methoxysinensetin, 4) and 5’-hydroxy-3,6,7,3’,4’-pentamethoxyflavone (5) were synthesized. Their anti-proliferative activity in?vitro was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2 and SUN-5) by the CTG assay. The results showed that most of the synthetic compounds exhibited moderate to high anti-proliferative activities. In particular, compound 3c possess IC50 (5.30 μM) values below 10 μM against Aspc-1 cells and are worthy of further investigation.
Li, Wei,Liu, Kexiong,Su, Liang,Wang, Qiuan
supporting information

(2021/08/12)

Nobiletin derivative or pharmaceutically acceptable salt thereof as well as preparation method and application thereof
The invention discloses a nobiletin derivative or a pharmaceutically acceptable salt thereof as well as a preparation method and application thereof. The nobiletin derivative has a structural formula(I) shown in the description, in the formula, R1, R2, R3 and R4 are respectively selected from hydrogen, halogen, hydroxyl, amino, C1-6 substituted or non-substituted alkoxy, a C1-6 substituted or non-substituted ester group, C1-6 substituted or non-substituted alkamino and a C1-6 substituted or non-substituted amide group; R5 is selected from a C3-9 substituted or non-substituted aromatic ring and a C3-9 substituted or non-substituted aromatic heterocyclic ring; and X is selected from O or NR6. The nobiletin derivative or the pharmaceutically acceptable salt thereof, which is disclosed by theinvention, is novel in structure, and in addition, the compound has an excellent inhibition function on P-gp, can be prepared into a P-gp inhibitor, is capable of treating and/or preventing related diseases caused by P-gp, particularly diseases related to tumor drug resistance, or can be mixed and used with other medicines and used as a drug resistance reversal agent, has a high reversion multiple, and is capable of remarkably improving medicine effects of medicines.
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Paragraph 0097; 0102-0104

(2019/12/09)

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; 51

(2017/07/01)

Semi-synthesis and NMR spectral assignments of flavonoid and chalcone derivatives
Previous investigations of the aerial parts of the Australian plant Eremophila microtheca and Syzygium tierneyanum resulted in the isolation of the antimicrobial flavonoid jaceosidin (4) and 2′,6′-dihydroxy-4′-methoxy-3′,5′-dimethyl chalcone (7), respecti
Kumar, Rohitesh,Lu, Yuting,Elliott, Alysha G.,Kavanagh, Angela M.,Cooper, Matthew A.,Davis, Rohan A.
p. 880 - 886
(2016/10/25)

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; 0235

(2015/07/22)

Flavonoids with M1 muscarinic acetylcholine receptor binding activity
Muscarinic acetylcholine receptor- Active compounds have potential for the treatment of Alzheimer's disease. In this study, a series of natural and synthetic flavones and flavonols was assayed in vitro for their ability to inhibit radioligand binding at human cloned M1 muscarinic receptors. Several compounds were found to possess competitive binding affinity (K i = 40-110 μM), comparable to that of acetylcholine (Ki = 59 μM). Despite the fact that these compounds lack a positively-charged ammonium group under physiological conditions, molecular modelling studies suggested that they bind to the orthosteric site of the receptor, mainly through non-polar interactions.
Swaminathan, Meyyammai,Chee, Chin Fei,Chin, Sek Peng,Buckle, Michael J. C.,Rahman, Noorsaadah Abd.,Doughty, Stephen W.,Chung, Lip Yong
p. 8933 - 8948
(2014/08/05)

Synthesis of sinensetin, a naturally occurring polymethoxyflavone
5, 6, 7, 3′, 4′-Pentamethoxyflavone (8) isolated from the leaves of Orthosiphon stamineus has been synthesized by following an unambiguous route. All the new products have been characterised on the basis of spectral data and microanalysis.
Hossain, M. Amzad,Ismail, Zhari
p. 268 - 271
(2007/10/03)

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)

Synthesis of Highly Functionalized Flavones and Chromones Using Cycloacylation Reactions and C-3 Functionalization. A Total Synthesis of Hormothamnione
The cycloacylations of hydroxy- and methoxy-substituted phenols with aryl- and alkylpropiolic acids using Eaton's reagent (10percent phosphorus pentoxide in methanesulfonic acid) gives highly substituted flavones and chromones in up to 63 percent yield.Styrylchromones were prepared from 2-methylchromones by condensation reactions of the 2-methyl group with various substituted benzaldehydes in sodium ethoxide and ethanol in almost quantitative yield.Methylation or hydroxylation at C-3 of these highly substituted flavones and styrylchromones was accomplished in a highly regioselective manner employing lithium diisopropylamide followed by quenching with an electrophile.Quenching of the initial anion with methyl triflate gave 3-methyl products while quenching of the initial anion with trimethylborate followed by oxidation gave 3-hydroxy products.A total synthesis of the naturally occurring styrylchromone hormothamnione, containing a 3-methyl substituent, is reported by use of these synthetic techniques.
McGarry, Lynda W.,Detty, Michael R.
p. 4349 - 4356
(2007/10/02)

Syntheses of 6-Hydroxyluteolin and Sinensetin by Wessely - Moser Rearrangement
Syntheses of 6-hydroxyluteolin (1) and sinensetin (2) are described.The compounds 6 and 7 afford 1 on Wessely - Moser rearrangement.The synthetic samples 1 and 2 are identical (m.m.p. and co-ir) with the authentic samples.
Shaw, S. C.,Azad, R.,Mandal, S. P.,Gandhi, R. S.
p. 107 - 109
(2007/10/02)

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)

FLAVONOIDS FROM ABRUS PRECATORIUS
Key Word Index: Abrus precatorius; Leguminosae; flavonoids; 6,4'-dimethoxy-7,3'-dihydroxyflavone; abrectorin; desmethoxycentaureidin 7-O-rutinoside.
Bhardwaj, D. K.,Bisht, M. S.,Mehta, C. K.
p. 2040 - 2041
(2007/10/02)