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SINENSETIN is a pentamethoxyflavone, which is a type of flavone molecule substituted by methoxy groups at positions 5, 6, 7, 3', and 4'. It is a primary reference substance with assigned absolute purity, taking into account chromatographic purity, water, residual solvents, and inorganic impurities. The exact purity value can be found on the certificate provided by PhytoLab GmbH & Co. KG.

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  • 2306-27-6 Structure
  • Basic information

    1. Product Name: SINENSETIN
    2. Synonyms: Orange flavonoids;6-Hydroxyluteolin 5,6,7,3′,4′-pentamethyl ether;SINENSETIN;3',4',5,6,7-PENTAMETHOXYFLAVONE;5,6,7,3',4'-PENTAMETHOXYFLAVONE;5,6,7,3'',4''-PENTAMETHOXYFLAVONE WITH HPLC;2-(3,4-Dimethoxyphenyl)-5,6,7-trimethoxy-4H-1-benzopyran-4-one;Pedalitin permethyl ether
    3. CAS NO:2306-27-6
    4. Molecular Formula: C20H20O7
    5. Molecular Weight: 372.37
    6. EINECS: N/A
    7. Product Categories: Penta-substituted Flavones;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
    8. Mol File: 2306-27-6.mol
    9. Article Data: 13
  • Chemical Properties

    1. Melting Point: 174-176°C
    2. Boiling Point: 547.76 °C at 760 mmHg
    3. Flash Point: 240.561 °C
    4. Appearance: white to beige/
    5. Density: 1.244 g/cm3
    6. Vapor Pressure: 4.73E-12mmHg at 25°C
    7. Refractive Index: 1.565
    8. Storage Temp.: 2-8°C
    9. Solubility: DMSO: soluble3mg/mL, clear (warmed)
    10. BRN: 345748
    11. CAS DataBase Reference: SINENSETIN(CAS DataBase Reference)
    12. NIST Chemistry Reference: SINENSETIN(2306-27-6)
    13. EPA Substance Registry System: SINENSETIN(2306-27-6)
  • Safety Data

    1. Hazard Codes: T
    2. Statements: 25
    3. Safety Statements: 22-24/25-45
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 2306-27-6(Hazardous Substances Data)

2306-27-6 Usage

Uses

Used in Pharmaceutical Industry:
SINENSETIN is used as an antiangiogenesis agent for inhibiting the formation of new blood vessels, which is crucial in controlling the growth and spread of cancer cells.
Used in Healthcare Industry:
SINENSETIN is used as an antidiabetic agent, potentially helping in the management and treatment of diabetes by regulating blood sugar levels.
Used in Antifungal Applications:
SINENSETIN is used as an antifungal agent, effective against various fungal infections due to its ability to inhibit fungal growth and activity.
Used in Antihistamine Applications:
SINENSETIN is used as an antihistamine agent, helping to alleviate symptoms caused by histamine release, such as allergies and inflammation.
Used in Cell Differentiation:
SINENSETIN is used to induce cell differentiation, which can be beneficial in the treatment of certain diseases and conditions where abnormal cell growth occurs.
Used in Inhibition of Linoleic Acid Oxidation:
SINENSETIN is used to inhibit linoleic acid oxidation, which can help prevent the formation of harmful free radicals and maintain overall health.
Used in Inhibition of White Blood Cells in Human Zona Protein Interleukin-1β Induced Expression of Tissue Factor:
SINENSETIN is used to inhibit the expression of tissue factor in white blood cells induced by human zona protein Interleukin-1β, which can be relevant in the context of immune response and inflammation.

Biochem/physiol Actions

Sinensetin is a citris flavonoid with anti-inflammatory and anti-proliferative activity. It has also been shown to enhance adipogenesis and lipolysis.

Check Digit Verification of cas no

The CAS Registry Mumber 2306-27-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,3,0 and 6 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2306-27:
(6*2)+(5*3)+(4*0)+(3*6)+(2*2)+(1*7)=56
56 % 10 = 6
So 2306-27-6 is a valid CAS Registry Number.
InChI:InChI=1/C20H20O7/c1-22-13-7-6-11(8-15(13)23-2)14-9-12(21)18-16(27-14)10-17(24-3)19(25-4)20(18)26-5/h6-10H,1-5H3

2306-27-6 Well-known Company Product Price

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  • Sigma-Aldrich

  • (89392)  Sinensetin  analytical standard

  • 2306-27-6

  • 89392-10MG

  • 5,654.61CNY

  • Detail

2306-27-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name sinensetin

1.2 Other means of identification

Product number -
Other names Pedalitin permethyl ether

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2306-27-6 SDS

2306-27-6Synthetic route

3,4-dimethoxybenzoic acid chloride
3535-37-3

3,4-dimethoxybenzoic acid chloride

Eudesmic acid
118-41-2

Eudesmic acid

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Stage #1: 3,4-dimethoxybenzoic acid chloride; Eudesmic acid With triethylamine In dichloromethane at 0 - 20℃; for 2h;
Stage #2: With trimethylsilyl trifluoromethanesulfonate; triethylamine In dichloromethane at 95℃; for 2h;
81%
(E)-3-(3,4-dimethoxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one
114021-62-4

(E)-3-(3,4-dimethoxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With pyridine; iodine for 8h; Heating;71%
With selenium(IV) oxide; pentan-1-ol
3,4-dimethoxyphenylpropiolic acid
22511-06-4

3,4-dimethoxyphenylpropiolic acid

3,4,5-trimethoxyphenol
642-71-7

3,4,5-trimethoxyphenol

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With phosphorus pentaoxide; methanesulfonic acid for 4h; Ambient temperature;26%
jaceosidin
18085-97-7

jaceosidin

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
In methanol; dichloromethane for 16h;24%
3,6-dihydroxy-2,4-dimethoxyacetophenone
6962-57-8

3,6-dihydroxy-2,4-dimethoxyacetophenone

3,4-dimethoxybenzoic anhydride
24824-54-2

3,4-dimethoxybenzoic anhydride

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With sodium 3,4-dimethoxybenzoate at 180℃; unter vermindertem Druck; Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge und Behandeln des danach isolierten Reaktionsprodukts mit Dimethylsulfat, Kaliumcarbonat und Aceton;
3',4',5,6,7-pentahydroxyflavone
18003-33-3

3',4',5,6,7-pentahydroxyflavone

dimethyl sulfate
77-78-1

dimethyl sulfate

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With potassium carbonate; acetone
With potassium carbonate In acetone for 20h; Heating;70 mg
With potassium carbonate In acetone for 2h; Heating;0.200 g
4'-hydroxy-5,6,7,3'-tetramethoxyflavone
51145-80-3

4'-hydroxy-5,6,7,3'-tetramethoxyflavone

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
In diethyl ether
5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-6-methoxy-chromen-4-one
22934-99-2

5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-6-methoxy-chromen-4-one

dimethyl sulfate
77-78-1

dimethyl sulfate

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With potassium carbonate In acetone
3',4',7-trihydroxy-5,6-dimethoxyflavone
88153-47-3

3',4',7-trihydroxy-5,6-dimethoxyflavone

dimethyl sulfate
77-78-1

dimethyl sulfate

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With potassium carbonate In acetone for 4h;
selenium(IV) oxide
7446-08-4

selenium(IV) oxide

pentan-1-ol
71-41-0

pentan-1-ol

(E)-3-(3,4-dimethoxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one
114021-62-4

(E)-3-(3,4-dimethoxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one

sinensetin
2306-27-6

sinensetin

2'-hydroxy-3,4,4',6'-tetramethoxychalcone

2'-hydroxy-3,4,4',6'-tetramethoxychalcone

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 65 percent / dimethyl dioxirane / acetone; CH2Cl2 / 1 h / 0 - 20 °C
2: 95 percent / K2CO3 / acetone / 6 h / Heating
3: 71 percent / I2; pyridine / 8 h / Heating
View Scheme
1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone
76650-20-9

1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
2: 65 percent / dimethyl dioxirane / acetone; CH2Cl2 / 1 h / 0 - 20 °C
3: 95 percent / K2CO3 / acetone / 6 h / Heating
4: 71 percent / I2; pyridine / 8 h / Heating
View Scheme
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / KOH / ethanol / 3 h / 20 °C
2: 90 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
3: 65 percent / dimethyl dioxirane / acetone; CH2Cl2 / 1 h / 0 - 20 °C
4: 95 percent / K2CO3 / acetone / 6 h / Heating
5: 71 percent / I2; pyridine / 8 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: ethanol; aq. NaOH solution
2: selenium dioxide; amyl alcohol
View Scheme
1-(2,4,6-trimethoxyphenyl)ethanone
832-58-6

1-(2,4,6-trimethoxyphenyl)ethanone

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / KOH / ethanol / 3 h / 20 °C
2: 90 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
3: 65 percent / dimethyl dioxirane / acetone; CH2Cl2 / 1 h / 0 - 20 °C
4: 95 percent / K2CO3 / acetone / 6 h / Heating
5: 71 percent / I2; pyridine / 8 h / Heating
View Scheme
1-(2,5-dihydroxy-4,6-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone

1-(2,5-dihydroxy-4,6-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / K2CO3 / acetone / 6 h / Heating
2: 71 percent / I2; pyridine / 8 h / Heating
View Scheme
6-hydroxy-2,3,4-trimethoxyacetophenone
22248-14-2

6-hydroxy-2,3,4-trimethoxyacetophenone

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 110 °C
2: pyridine; potassium hydroxide / 4 h / 60 °C
3: acetic acid; sulfuric acid / 16 h / Reflux
View Scheme
3,4-dimethoxybenzoic acid chloride
3535-37-3

3,4-dimethoxybenzoic acid chloride

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 110 °C
2: pyridine; potassium hydroxide / 4 h / 60 °C
3: acetic acid; sulfuric acid / 16 h / Reflux
View Scheme
2-Hydroxy-4,5,6,3',4'-pentamethoxydibenzoylmethane

2-Hydroxy-4,5,6,3',4'-pentamethoxydibenzoylmethane

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With sulfuric acid; acetic acid for 16h; Reflux;
3,4,5-trimethoxyphenol
642-71-7

3,4,5-trimethoxyphenol

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium acetate / 2 h / 110 °C
2.1: boron trifluoride diethyl etherate; acetic acid / 4 h / 70 °C
3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
3.2: 2 h / 95 °C
View Scheme
sinensetin
2306-27-6

sinensetin

5-desmethylsinensetin
21763-80-4

5-desmethylsinensetin

Conditions
ConditionsYield
With hydrogenchloride; ethanol for 72h; Product distribution / selectivity; Heating / reflux;100%
With boron tribromide In dichloromethane at 0℃; for 0.5h;94%
With boron trichloride In tetrahydrofuran at -78℃;61%
With boron trichloride In dichloromethane
sinensetin
2306-27-6

sinensetin

3',4',5,6,7-pentahydroxyflavone
18003-33-3

3',4',5,6,7-pentahydroxyflavone

Conditions
ConditionsYield
With hydrogen iodide; acetic anhydride
sinensetin
2306-27-6

sinensetin

Veratric acid
93-07-2

Veratric acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 24h; Heating;3.4 mg
sinensetin
2306-27-6

sinensetin

1-(2,3,4,6-tetramethoxyphenyl)ethanone
7508-05-6

1-(2,3,4,6-tetramethoxyphenyl)ethanone

Conditions
ConditionsYield
(i) aq. KOH, EtOH, (ii) (methylation); Multistep reaction;
sinensetin
2306-27-6

sinensetin

5,8-dihydroxy-6,7-dimethoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone
683278-67-3

5,8-dihydroxy-6,7-dimethoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
2: 90 percent / dimethyl dioxirane / acetone; CH2Cl2 / 0.33 h / 0 - 20 °C
View Scheme
sinensetin
2306-27-6

sinensetin

nobiletin
478-01-3

nobiletin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
2: 90 percent / dimethyl dioxirane / acetone; CH2Cl2 / 0.33 h / 0 - 20 °C
3: 87 percent / K2CO3 / acetone; CH2Cl2 / 6 h / Heating
View Scheme
sinensetin
2306-27-6

sinensetin

3-hydroxy-5,6,7,8,3′,4′-hexamethoxyflavone
35154-55-3

3-hydroxy-5,6,7,8,3′,4′-hexamethoxyflavone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 94 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
2: 90 percent / dimethyl dioxirane / acetone; CH2Cl2 / 0.33 h / 0 - 20 °C
3: 87 percent / K2CO3 / acetone; CH2Cl2 / 6 h / Heating
4: 80 percent / dimethyl dioxirane / acetone; CH2Cl2 / 0.17 h / 0 - 20 °C
View Scheme
sinensetin
2306-27-6

sinensetin

3,3',4',5,6,7,8-heptamethoxyflavone
1178-24-1

3,3',4',5,6,7,8-heptamethoxyflavone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 94 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
2: 90 percent / dimethyl dioxirane / acetone; CH2Cl2 / 0.33 h / 0 - 20 °C
3: 87 percent / K2CO3 / acetone; CH2Cl2 / 6 h / Heating
4: 80 percent / dimethyl dioxirane / acetone; CH2Cl2 / 0.17 h / 0 - 20 °C
5: 97 percent / K2CO3 / acetone / 1 h / Heating
View Scheme
5,6,7,4'-tetramethoxyflavone
1168-42-9

5,6,7,4'-tetramethoxyflavone

sinensetin
2306-27-6

sinensetin

tangeritin
481-53-8

tangeritin

3,5,6,7,3',4'-Hexamethoxyflavon
1251-84-9

3,5,6,7,3',4'-Hexamethoxyflavon

nobiletin
478-01-3

nobiletin

3,3',4',5,6,7,8-heptamethoxyflavone
1178-24-1

3,3',4',5,6,7,8-heptamethoxyflavone

A

gardenin B
2798-20-1

gardenin B

B

5-hydroxy-4',6,7-trimethoxyflavone
19103-54-9

5-hydroxy-4',6,7-trimethoxyflavone

C

5-desmethylsinensetin
21763-80-4

5-desmethylsinensetin

D

artemetin
479-90-3

artemetin

E

5-hydroxy-6,7,8,3',4'-pentamethoxyflavone
2174-59-6

5-hydroxy-6,7,8,3',4'-pentamethoxyflavone

F

5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone
1176-88-1

5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone

Conditions
ConditionsYield
With hydrogenchloride; ethanol at 80℃; for 18 - 70h; Product distribution / selectivity; Heating / reflux;
With hydrogenchloride; ethanol; water at 80℃; for 18h; Conversion of starting material; Heating / reflux;
With ethanol; water for 24h; Product distribution / selectivity; Heating / reflux;

2306-27-6Relevant articles and documents

5,6-DIMETHOXY-7,3',4',-TRIHYDROXYFLAVONE FROM ANISOMELES OVATA

Rao, L. Jagan Mohan,Kumari, G. N. Krishna,Rao, N. S. Prakasa

, p. 1522 (1983)

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.

Synthesis and anti-proliferative activities of 5,6,7-trimethoxyflavones and their derivatives

Li, Wei,Liu, Kexiong,Su, Liang,Wang, Qiuan

, (2021/08/12)

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.

Nobiletin derivative or pharmaceutically acceptable salt thereof as well as preparation method and application thereof

-

Paragraph 0097; 0102-0104, (2019/12/09)

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.

Use of flavone and flavanone derivatives in preparation of sedative and hypnotic drugs

-

Page/Page column 48; 49; 50; 51, (2017/07/01)

Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.

Semi-synthesis and NMR spectral assignments of flavonoid and chalcone derivatives

Kumar, Rohitesh,Lu, Yuting,Elliott, Alysha G.,Kavanagh, Angela M.,Cooper, Matthew A.,Davis, Rohan A.

, p. 880 - 886 (2016/10/25)

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

USE OF FLAVONE AND FLAVANONE DERIVATIVES IN PREPARATION OF SEDATIVE AND HYPNOTIC DRUGS

-

Paragraph 0223; 0235, (2015/07/22)

Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.

Flavonoids with M1 muscarinic acetylcholine receptor binding activity

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)

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.

Synthesis of sinensetin, a naturally occurring polymethoxyflavone

Hossain, M. Amzad,Ismail, Zhari

, p. 268 - 271 (2007/10/03)

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.

Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

Chu, Han-Wei,Wu, Huan-Ting,Lee, Yean-Jang

, p. 2647 - 2655 (2007/10/03)

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.

Synthesis of Highly Functionalized Flavones and Chromones Using Cycloacylation Reactions and C-3 Functionalization. A Total Synthesis of Hormothamnione

McGarry, Lynda W.,Detty, Michael R.

, p. 4349 - 4356 (2007/10/02)

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.

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