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38183-03-8

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38183-03-8 Usage

Description

7,8-Dihydroxyflavone(7,8-DHF) is a naturally occurring flavone found in the tree Godmania aesculifolia. It is a selective tyrosine kinase receptor B(TrkB) agonist that has neurotrophic effects in various neurological diseases such as stroke and Parkinson's disease. 7,8-Dihydroxyflavone binds to the TrkB receptors in a similar way to BDNF, or brain derived neurotrophic factor. When the TrkB receptor is activated, neuroprotective and neurogenetive effects occur in neurons, which tend to affect the dendrites. Dendrites are what reach out from the neurons into the synapse to participate in signaling with other neurons. 7,8-DHF has been shown to promote the growth of these dendrites, and to help restore communication between neurons in animal models.

Chemical Properties

White crystalline powder or Yellow Solid, soluble in methanol, ethanol, DMSO and other organic solvents, from the dried root of Pulsatilla chinensis (Bge.) Regel.

Uses

7,8-Dihydroxyflavone is disubstituted flavone that acts as a small-molecule TrkB agonist. 7,8-Dihydroxyflavone has been shown to reverse memory deficits and BACE1 elevation in a mouse model of Alzheimer''s disease. 7,8-Dihydroxyflavone may also provide a therapeutic option in the treatment of other neorological disorders such as Rett syndrome and PTSD. It has recently been shown to counteract the inhibition of NMDA receptor caused by lead poisoning and confer protective effects in live rats.

Biological Activity

7,8-Dihydroxyflavone (7,8-DHF) is a monophenolic flavone with diverse effects. It acts as an agonist of the neurotrophic tyrosine kinase receptor TrkB (Kd = 320 nM), protecting neurons that express TrkB from apoptosis. 7,8-DHF is neuroprotective in an animal model of Parkinson’s disease. It supports emotional learning in mice and reverses memory deficits in a mouse model of Alzheimer’s disease. It also improves motor function and extends survival in an animal model of Huntington’s disease. 7,8-DHF inhibits the cytochrome P450 aromatase (IC50 = 10 μM) and, in this way, alters estrogen metabolism. It also has antioxidant action that increases intracellular glutathione synthesis and scavenges reactive oxygen species.

Biochem/physiol Actions

7,8-Dihydroxyflavone is a selective tyrosine kinase receptor B (TrkB) receptor agonist. It manifests all the therapeutic effects of brain-derived neurotrophic factor (BDNF)—such as protecting neurons from apoptosis, inhibiting kainic acid-induced toxicity, decreasing infarct volumes in stroke, and neuroprotecting in an animal model of Parkinson′s disease—without the poor pharmacokinetic profile of BDNF limiting its therapeutic potential.

Side effects

As with any other drug, 7,8-DHF is not without its side effects. However, there are not as many side effects associated with the use of 7,8-DHF as it is a natural product.The following are some reported side effects associated with the use of 7,8-DHF or products that contain it:OverstimulationRestlessnessDizzinessNauseaIrritabilityTrouble sleeping

Mode of action

7,8-Dihydroxyflavone (7,8-DHF, tropoflavin) is the most common and effective flavone identified in Sophora plants.7,8-DHF mimics the effects of brain-derived neurotrophic factor (BDNF) in brain cells by activating tropomyosin-related kinase B (TrkB) receptors, the typical target of BDNF.The therapeutic potential of BDNF is restricted due to its short half-life (less than 10 minutes) and its inability to cross the blood-brain barrier because of its large size. Unlike BDNF 7,8-DHF is able to penetrate the blood-brain barrier and enter the central nervous system (CNS) .7,8-DHF also increases the production of Nrf2. Nrf2 increases antioxidants enzymes such as heme oxygenase 1 (HO-1) and also enzymes that repair DNA (8-oxoguanine DNA glycosylase-1 – OGG1) .

References

1) Jang et al. (2010), A selective TrkB agonist with potent neurotrophic activities by 7,8-dihydroxyflavone; Proc. Natl. Acad. Sci. USA, 107 2687 2) Liu et al. (2014) Biochemical and biophysical investigation of the brain-derived neurotrophic factor mimetic 7,8-dihydroxyflavone in the binding and activation of the TrkB receptor; J. Biol. Chem., 289 27571 3) Jiang et al. (2013) Small-molecule TrkB receptor agonist improve motor function and extend survival in a mouse model of Huntington’s disease; Hum. Mol. Genet., 22 2462 4) Zhao et al. (2016) Post-injury Treatment of 7,8-Dihydroxyflavone Promotes Neurogenesis in the Hippocampus of the Adult Mouse; J. Neurotrauma, 33 2055 5) Korkmaz et al. (2014) 7,8-dihydroxyflavone improves motor performance and enhances lower motor neuronal survival in a mouse model of amyotrophic lateral sclerosis; Neurosci. Lett., 566 286

Check Digit Verification of cas no

The CAS Registry Mumber 38183-03-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,8,1,8 and 3 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 38183-03:
(7*3)+(6*8)+(5*1)+(4*8)+(3*3)+(2*0)+(1*3)=118
118 % 10 = 8
So 38183-03-8 is a valid CAS Registry Number.
InChI:InChI=1/C15H10O4/c16-11-7-6-10-12(17)8-13(19-15(10)14(11)18)9-4-2-1-3-5-9/h1-8,16,18H

38183-03-8 Well-known Company Product Price

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  • TCI America

  • (D1916)  7,8-Dihydroxyflavone Hydrate  >98.0%(HPLC)(T)

  • 38183-03-8

  • 1g

  • 730.00CNY

  • Detail
  • TCI America

  • (D1916)  7,8-Dihydroxyflavone Hydrate  >98.0%(HPLC)(T)

  • 38183-03-8

  • 5g

  • 2,640.00CNY

  • Detail
  • Sigma

  • (D5446)  7,8-Dihydroxyflavone hydrate  ≥98% (HPLC)

  • 38183-03-8

  • D5446-10MG

  • 745.29CNY

  • Detail
  • Sigma

  • (D5446)  7,8-Dihydroxyflavone hydrate  ≥98% (HPLC)

  • 38183-03-8

  • D5446-50MG

  • 2,955.42CNY

  • Detail

38183-03-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 7,8-DIHYDROXYFLAVONE

1.2 Other means of identification

Product number -
Other names 7,8-dihydroxy-2-phenylchromen-4-one

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:38183-03-8 SDS

38183-03-8Synthetic route

7-hydroxyflavone
6665-86-7

7-hydroxyflavone

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 80℃; for 24h;98%
With dipotassium peroxodisulfate; alkaline solution Erwaermen des Reaktionsprodukts mit wss. Salzsaeure;
Multi-step reaction with 2 steps
1: aluminium chloride / 160 °C
2: aq. NaOH solution; aqueous hydrogen peroxide
View Scheme
With cytochromes P450 in human liver microsomes Kinetics; Enzymatic reaction;
C29H22O4
500866-00-2

C29H22O4

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In tetrahydrofuran; methanol at 40℃; under 4560.31 - 6080.41 Torr;90.5%
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol at 20℃; for 3h;83%
C29H18O6
110865-10-6

C29H18O6

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
With sodium methylate In ethanol; dichloromethane63%
With water; sodium hydroxide In 1,4-dioxane; methanol at 20℃;
8-acetyl-7-hydroxy-2-phenyl-chromen-4-one
42345-27-7

8-acetyl-7-hydroxy-2-phenyl-chromen-4-one

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide
1-(3,4-bis-benzoyloxy-2-hydroxy-phenyl)-3-phenyl-propane-1,3-dione
856084-77-0

1-(3,4-bis-benzoyloxy-2-hydroxy-phenyl)-3-phenyl-propane-1,3-dione

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
With sodium acetate; acetic acid Erwaermen des Reaktionsprodukts mit methanol. Kalilauge;
ethyl 3-oxo-3-phenylpropionate
94-02-0

ethyl 3-oxo-3-phenylpropionate

2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
With diphenylether
1-(3,4-bis-benzoyloxy-2-hydroxy-phenyl)-3-phenyl-propane-1,3-dione
856084-77-0

1-(3,4-bis-benzoyloxy-2-hydroxy-phenyl)-3-phenyl-propane-1,3-dione

sodium acetate
127-09-3

sodium acetate

acetic acid
64-19-7

acetic acid

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
anschliessend Erhitzen mit wss.-methanol. Kalilauge;
2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
With aluminium trichloride; nitrobenzene Behandeln der Reaktionsloesung mit Phenylpropioloylchlorid und Benzol;
Multi-step reaction with 6 steps
1: boron trifluoride diethyl etherate / 50 - 100 °C / Inert atmosphere; Large scale
2: potassium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / 6 h / 90 - 110 °C / Inert atmosphere; Large scale
3: hydrogenchloride; acetic acid / water / 3 h / 20 °C
4: potassium hydroxide / water; ethanol / 20 - 30 °C
5: iodine / dimethyl sulfoxide / 7 h / 110 °C / Inert atmosphere
6: palladium on activated charcoal; hydrogen / methanol; tetrahydrofuran / 40 °C / 4560.31 - 6080.41 Torr
View Scheme
1-Phenyl-3-(2,3,4-trihydroxy-phenyl)-propane-1,3-dione
131944-43-9

1-Phenyl-3-(2,3,4-trihydroxy-phenyl)-propane-1,3-dione

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
With sulfuric acid In acetic acid at 95 - 100℃; Yield given;
benzoic acid anhydride
93-97-0

benzoic acid anhydride

2.3.4-trioxy-acetophenone

2.3.4-trioxy-acetophenone

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
With sodium benzoate at 180 - 185℃; Kochen des Reaktionsprodukts mit waessrig-alkoholischer Kalilauge;
7.8-dimethoxy-flavone

7.8-dimethoxy-flavone

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
With hydrogen iodide
7-hydroxyflavone
6665-86-7

7-hydroxyflavone

aqueous alkaline solution

aqueous alkaline solution

potassium peroxo disulfate

potassium peroxo disulfate

A

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

B

7-hydroxy-2-phenyl-8-sulfooxy-chromen-4-one

7-hydroxy-2-phenyl-8-sulfooxy-chromen-4-one

2',3',4'-trihydroxyacetophenone
528-21-2

2',3',4'-trihydroxyacetophenone

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) lithium bis(trimethyl)silyl amide (LiHMDS) / 1) THF, a) -78 deg C, b) -10 deg C, 2) THF, a) -78 deg C, b) room temp.
2: H2SO4 / acetic acid / 95 - 100 °C
View Scheme
Multi-step reaction with 2 steps
1: pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene / 24 h / 120 - 140 °C
2: water; sodium hydroxide / 1,4-dioxane; methanol / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 8 h / 50 °C
2.1: trifluoroacetic acid / toluene / 2 h / 20 °C
3.1: potassium hydroxide / ethanol; water / 36 h / 20 °C
3.2: pH Ca. 5 / Cooling with ice
4.1: iodine; dimethyl sulfoxide / 12 h / 110 °C
5.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: potassium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / 6 h / 90 - 110 °C / Inert atmosphere; Large scale
2: hydrogenchloride; acetic acid / water / 3 h / 20 °C
3: potassium hydroxide / water; ethanol / 20 - 30 °C
4: iodine / dimethyl sulfoxide / 7 h / 110 °C / Inert atmosphere
5: palladium on activated charcoal; hydrogen / methanol; tetrahydrofuran / 40 °C / 4560.31 - 6080.41 Torr
View Scheme
benzoyl chloride
98-88-4

benzoyl chloride

O5-benzoyl-O1,O2-isopropyliden-β-D-arabinofuranose

O5-benzoyl-O1,O2-isopropyliden-β-D-arabinofuranose

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) lithium bis(trimethyl)silyl amide (LiHMDS) / 1) THF, a) -78 deg C, b) -10 deg C, 2) THF, a) -78 deg C, b) room temp.
2: H2SO4 / acetic acid / 95 - 100 °C
View Scheme
4-oxo-2-phenyl-4H-chromen-7-yl acetate
72994-98-0

4-oxo-2-phenyl-4H-chromen-7-yl acetate

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aluminium chloride / 60 °C
2: aq. NaOH solution; aqueous hydrogen peroxide
View Scheme
C29H24O4
93827-33-9

C29H24O4

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iodine; dimethyl sulfoxide / 12 h / 110 °C
2: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C
View Scheme
1-(2,3,4-tris(benzyloxy)phenyl)ethanone
50439-63-9

1-(2,3,4-tris(benzyloxy)phenyl)ethanone

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: trifluoroacetic acid / toluene / 2 h / 20 °C
2.1: potassium hydroxide / ethanol; water / 36 h / 20 °C
2.2: pH Ca. 5 / Cooling with ice
3.1: iodine; dimethyl sulfoxide / 12 h / 110 °C
4.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride; acetic acid / water / 3 h / 20 °C
2: potassium hydroxide / water; ethanol / 20 - 30 °C
3: iodine / dimethyl sulfoxide / 7 h / 110 °C / Inert atmosphere
4: palladium on activated charcoal; hydrogen / methanol; tetrahydrofuran / 40 °C / 4560.31 - 6080.41 Torr
View Scheme
1-(3,4-bis(benzyloxy)-2-hydroxyphenyl)ethanone
2652-27-9

1-(3,4-bis(benzyloxy)-2-hydroxyphenyl)ethanone

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydroxide / ethanol; water / 36 h / 20 °C
1.2: pH Ca. 5 / Cooling with ice
2.1: iodine; dimethyl sulfoxide / 12 h / 110 °C
3.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium hydroxide / water; ethanol / 20 - 30 °C
2: iodine / dimethyl sulfoxide / 7 h / 110 °C / Inert atmosphere
3: palladium on activated charcoal; hydrogen / methanol; tetrahydrofuran / 40 °C / 4560.31 - 6080.41 Torr
View Scheme
2',3',4'-trihydroxyacetophenone
528-21-2

2',3',4'-trihydroxyacetophenone

benzoyl chloride
98-88-4

benzoyl chloride

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
Stage #1: 2',3',4'-trihydroxyacetophenone; benzoyl chloride With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene for 8h; Reflux;
Stage #2: With sodium hydroxide In 1,4-dioxane; methanol
Stage #1: 2',3',4'-trihydroxyacetophenone; benzoyl chloride With potassium carbonate In acetone for 12.1667h; Baker-Venkataraman Rearrangement; Inert atmosphere; Reflux;
Stage #2: In methanol; water for 3h; Inert atmosphere; Reflux;
2'-hydroxy-3',4'-dimethoxyacetophenone
5396-18-9

2'-hydroxy-3',4'-dimethoxyacetophenone

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: pyridine / 1 h / 75 °C
2.1: pyridine; potassium hydroxide / 2 h / 50 - 75 °C
3.1: acetic acid; sulfuric acid / 1 h / 90 - 110 °C
3.2: 0.5 h / 0 - 20 °C
4.1: boron tribromide / dichloromethane / Heating
View Scheme
7,8-dimethoxyflavone
65548-54-1

7,8-dimethoxyflavone

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
With boron tribromide In dichloromethane Heating;
1-(2-benzoyloxy-3,4-dimethoxy-phenyl)-ethanone

1-(2-benzoyloxy-3,4-dimethoxy-phenyl)-ethanone

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridine; potassium hydroxide / 2 h / 50 - 75 °C
2.1: acetic acid; sulfuric acid / 1 h / 90 - 110 °C
2.2: 0.5 h / 0 - 20 °C
3.1: boron tribromide / dichloromethane / Heating
View Scheme
1-(2-hydroxy-3,4-dimethoxy-phenyl)-3-phenyl-propane-1,3-dione
169788-03-8

1-(2-hydroxy-3,4-dimethoxy-phenyl)-3-phenyl-propane-1,3-dione

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: acetic acid; sulfuric acid / 1 h / 90 - 110 °C
1.2: 0.5 h / 0 - 20 °C
2.1: boron tribromide / dichloromethane / Heating
View Scheme
7-hydroxyflavone
6665-86-7

7-hydroxyflavone

A

7,4'-Dihydroxyflavon
2196-14-7

7,4'-Dihydroxyflavon

B

6,7-dihydroxyflavone
38183-04-9

6,7-dihydroxyflavone

C

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
With cytochromes P450 in human liver microsomes Kinetics; Enzymatic reaction;
FLAVONE
525-82-6

FLAVONE

A

7,4'-Dihydroxyflavon
2196-14-7

7,4'-Dihydroxyflavon

B

6,7-dihydroxyflavone
38183-04-9

6,7-dihydroxyflavone

C

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: cytochromes P450 in human liver microsomes / Enzymatic reaction
2: cytochromes P450 in human liver microsomes / Enzymatic reaction
View Scheme
FLAVONE
525-82-6

FLAVONE

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: cytochromes P450 in human liver microsomes / Enzymatic reaction
2: cytochromes P450 in human liver microsomes / Enzymatic reaction
View Scheme
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

methyl iodide
74-88-4

methyl iodide

7,8-dimethoxyflavone
65548-54-1

7,8-dimethoxyflavone

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 2h;94%
With potassium carbonate In acetone at 60℃;
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

allyl bromide
106-95-6

allyl bromide

2-phenyl-7,8-bis(prop-2-en-1-yloxy)-4H-1-benzopyran-4-one

2-phenyl-7,8-bis(prop-2-en-1-yloxy)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 4h; Inert atmosphere; Reflux;78%
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

7,8-dihydroxy 4-thioflavone

7,8-dihydroxy 4-thioflavone

Conditions
ConditionsYield
With Lawessons reagent In toluene at 40℃; for 0.5h; Substitution;77%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

4-oxo-2-phenyl-4H-chromene-7,8-diyl Bis(trifluoromethanesulfonate)
1257063-84-5

4-oxo-2-phenyl-4H-chromene-7,8-diyl Bis(trifluoromethanesulfonate)

Conditions
ConditionsYield
With pyridine In dichloromethane at -78 - 0℃; Inert atmosphere;76%
Stage #1: 7,8-dihydroxyflavone With pyridine In dichloromethane at -78℃; for 0.166667h; Inert atmosphere;
Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at -78 - 0℃; Inert atmosphere;
76%
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

triethylamine
121-44-8

triethylamine

[Et3NH]2[{(O2)C15H8O2}3Si]

[Et3NH]2[{(O2)C15H8O2}3Si]

Conditions
ConditionsYield
With tetraethoxy orthosilicate In acetonitrile at 20℃; for 24h; Inert atmosphere;70%
3-chloro-3-methylbut-1-yne
1111-97-3

3-chloro-3-methylbut-1-yne

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

1,8-diazabicyclo[5.4.0]undec-7-ene
6674-22-2

1,8-diazabicyclo[5.4.0]undec-7-ene

7,8-bis-(1,1-dimethyl-prop-2-ynyloxy)-2-phenyl-4H-chromen-4-one
786706-00-1

7,8-bis-(1,1-dimethyl-prop-2-ynyloxy)-2-phenyl-4H-chromen-4-one

Conditions
ConditionsYield
With CuCl2 In acetonitrile69%
3-chloro-3-methylbut-1-yne
1111-97-3

3-chloro-3-methylbut-1-yne

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

7,8-bis-(1,1-dimethyl-prop-2-ynyloxy)-2-phenyl-4H-chromen-4-one
786706-00-1

7,8-bis-(1,1-dimethyl-prop-2-ynyloxy)-2-phenyl-4H-chromen-4-one

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; copper dichloride In acetonitrile at 0 - 20℃;69%
With copper(l) iodide; potassium carbonate; potassium iodide In acetone at 50℃; for 4h;62%
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

ethylenediamine
107-15-3

ethylenediamine

4-(7-phenyl-2,3-dihydro-1H-1,4-diazepin-5-yl)benzene-1,2,3-triol

4-(7-phenyl-2,3-dihydro-1H-1,4-diazepin-5-yl)benzene-1,2,3-triol

Conditions
ConditionsYield
In ethanol at 100℃;56%
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

acetic anhydride
108-24-7

acetic anhydride

4-oxo-2-phenyl-4H-chromene-7,8-diyl diacetate
109688-08-6

4-oxo-2-phenyl-4H-chromene-7,8-diyl diacetate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 20℃;53.3%
With potassium carbonate In dichloromethane at 20℃;53.3%
With sodium acetate
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

2,3-dibromopropionic acid ethyl ester
3674-13-3

2,3-dibromopropionic acid ethyl ester

A

7,8-<3-(Ethoxycarbonyl)-ethylenedioxy>-2-phenyl-4H-1-benzopyran-4-one
121869-37-2

7,8-<3-(Ethoxycarbonyl)-ethylenedioxy>-2-phenyl-4H-1-benzopyran-4-one

B

7,8-<2-(Ethoxycarbonyl)-ethylenedioxy>-2-phenyl-4H-1-benzopyran-4-one
121869-36-1

7,8-<2-(Ethoxycarbonyl)-ethylenedioxy>-2-phenyl-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 20h; Heating;A 8%
B 44%
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

2,3-dibromopropionic acid ethyl ester
3674-13-3

2,3-dibromopropionic acid ethyl ester

1360

1360

A

7,8-<3-(Ethoxycarbonyl)-ethylenedioxy>-2-phenyl-4H-1-benzopyran-4-one
121869-37-2

7,8-<3-(Ethoxycarbonyl)-ethylenedioxy>-2-phenyl-4H-1-benzopyran-4-one

B

7,8-<2-(Ethoxycarbonyl)-ethylenedioxy>-2-phenyl-4H-1-benzopyran-4-one
121869-36-1

7,8-<2-(Ethoxycarbonyl)-ethylenedioxy>-2-phenyl-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 20h; Heating;A 8%
B 44%
BOC-glycine
4530-20-5

BOC-glycine

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

C29H32N2O10
1609067-52-8

C29H32N2O10

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In pyridine for 24h; Cooling with ice;25%
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

isopentanoyl chloride
108-12-3

isopentanoyl chloride

4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(3-methylbutanoate)
1609067-34-6

4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(3-methylbutanoate)

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 20℃;23.1%
With potassium carbonate In dichloromethane at 20℃;23.1%
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

ethyl isocyanate
109-90-0

ethyl isocyanate

4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(ethylcarbamate)
1609067-38-0

4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(ethylcarbamate)

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 20℃;22.5%
With potassium carbonate In dichloromethane at 20℃;22.5%
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

5-deoxyscutellaprostin-A

5-deoxyscutellaprostin-A

Conditions
ConditionsYield
With silver carbonate In acetone; benzene at 60℃; for 24h;21%
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

pivaloyl chloride
3282-30-2

pivaloyl chloride

4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(2,2-dimethylpropanoate)
1609067-33-5

4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(2,2-dimethylpropanoate)

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 20℃;20.9%
With potassium carbonate In dichloromethane at 20℃;20.9%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(4-methylpiperazine-1-carboxylate).
1609067-46-0

4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(4-methylpiperazine-1-carboxylate).

Conditions
ConditionsYield
Stage #1: 1-methyl-piperazine; bis(trichloromethyl) carbonate In tetrahydrofuran at -78℃; for 1h;
Stage #2: 7,8-dihydroxyflavone In pyridine; water; acetone at 0 - 20℃;
20.2%
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

propionyl chloride
79-03-8

propionyl chloride

4-oxo-2-phenyl-4H-chromene-7,8-diyl dipropionate
1609067-36-8

4-oxo-2-phenyl-4H-chromene-7,8-diyl dipropionate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 20℃;17.4%
With potassium carbonate In dichloromethane at 20℃;17.4%
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

N,N-Dimethylcarbamoyl chloride
79-44-7

N,N-Dimethylcarbamoyl chloride

4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(dimethylcarbamate)
1609067-35-7

4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(dimethylcarbamate)

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 20℃;15.9%
With potassium carbonate In dichloromethane at 20℃;15.9%
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

diethyl (4-oxo-2-phenyl-4H-chromene-7,8-diyl) bis(carbonate)
1609067-37-9

diethyl (4-oxo-2-phenyl-4H-chromene-7,8-diyl) bis(carbonate)

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 20℃;15.9%
With potassium carbonate In dichloromethane at 20℃;15.9%
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

7,8-dimethoxyflavone
65548-54-1

7,8-dimethoxyflavone

Conditions
ConditionsYield
With diethyl ether
[1,3,5,7,2,6]tetroxadithiocane 2,2,6,6-tetraoxide
20757-83-9

[1,3,5,7,2,6]tetroxadithiocane 2,2,6,6-tetraoxide

7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

8-phenyl-[1,3]dioxolo[4,5-h]chromen-6-one
4476-32-8

8-phenyl-[1,3]dioxolo[4,5-h]chromen-6-one

Conditions
ConditionsYield
With potassium carbonate; acetone
7,8-dihydroxyflavone
38183-03-8

7,8-dihydroxyflavone

dimethyl sulfate
77-78-1

dimethyl sulfate

7,8-dimethoxyflavone
65548-54-1

7,8-dimethoxyflavone

Conditions
ConditionsYield
With potassium carbonate; acetone
With alkaline solution

38183-03-8Relevant articles and documents

-

Seka,Prosche

, p. 284,291 (1936)

-

Novel synthesised flavone derivatives provide significant insight into the structural features required for enhanced anti-proliferative activity

Ravishankar, Divyashree,Watson, Kimberly A.,Greco, Francesca,Osborn, Helen M. I.

, p. 64544 - 64556 (2016/07/21)

With many cancers showing resistance to current chemotherapies, the search for novel anti-cancer agents is attracting considerable attention. Natural flavonoids have been identified as useful leads in such programmes. However, since an in-depth understanding of the structural requirements for optimum activity is generally lacking, further research is required before the full potential of flavonoids as anti-proliferative agents can be realised. Herein a broad library of 76 methoxy and hydroxy flavones, and their 4-thio analogues, was constructed and their structure-activity relationships for anti-proliferative activity against the breast cancer cell lines MCF-7 (ER +ve), MCF-7/DX (ER +ve, anthracycline resistant) and MDA-MB-231 (ER -ve) were probed. Within this library, 42 compounds were novel, and all compounds were afforded in good yields and >95% purity. The most promising lead compounds, specifically the novel hydroxy 4-thioflavones 15f and 16f, were further evaluated for their anti-proliferative activities against a broader range of cancer cell lines by the National Cancer Institute (NCI), USA and displayed significant growth inhibition profiles (e.g. compound-15f: MCF-7 (GI50 = 0.18 μM), T-47D (GI50 = 0.03 μM) and MDA-MB-468 (GI50 = 0.47 μM) and compound-16f: MCF-7 (GI50 = 1.46 μM), T-47D (GI50 = 1.27 μM) and MDA-MB-231 (GI50 = 1.81 μM)). Overall, 15f and 16f exhibited 7-46 fold greater anti-proliferative potency than the natural flavone chrysin (2d). A systematic structure-activity relationship study against the breast cancer cell lines highlighted that free hydroxyl groups and the B-ring phenyl groups were essential for enhanced anti-proliferative activities. Substitution of the 4-CO functionality with a 4-CS functionality, and incorporation of electron withdrawing groups at C-4′ of the B-ring phenyl, also enhanced activity. Molecular docking and mechanistic studies suggest that the anti-proliferative effects of flavones 15f and 16f are mediated via ER-independent cleavage of PARP and downregulation of GSK-3β for MCF-7 and MCF-7/DX cell lines. For the MDA-MB-231 cell line, restoration of the wild-type p53 DNA binding activity of mutant p53 tumour suppressor gene was indicated.

Antimalarial activity of HIV-1 protease inhibitor in chromone series

Lerdsirisuk, Pradith,Maicheen, Chirattikan,Ungwitayatorn, Jiraporn

, p. 142 - 147 (2015/02/05)

Increasing parasite resistance to nearly all available antimalarial drugs becomes a serious problem to human health and necessitates the need to continue the search for new effective drugs. Recent studies have shown that clinically utilized HIV-1 protease (HIV-1 PR) inhibitors can inhibit the in vitro and in vivo growth of Plasmodium falciparum. In this study, a series of chromone derivatives possessing HIV-1 PR inhibitory activity has been tested for antimalarial activity against P. falciparum (K1 multi-drug resistant strain). Chromone 15, the potent HIV-1 PR inhibitor (IC50 = 0.65 μM), was found to be the most potent antimalarial compound with IC50 = 0.95 μM while primaquine and tafenoquine showed IC50 = 2.41 and 1.95 μM, respectively. Molecular docking study of chromone compounds against plasmepsin II, an aspartic protease enzyme important in hemoglobin degradation, revealed that chromone 15 exhibited the higher binding affinity (binding energy = -13.24 kcal/mol) than the known PM II inhibitors. Thus, HIV-1 PR inhibitor in chromone series has the potential to be a new class of antimalarial agent.

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