605-32-3

Usage

Uses

Used in Dye and Pigment Production:
2-Hydroxyanthraquinone is utilized as a key component in the creation of dyes and pigments due to its vibrant red-orange color, providing a wide range of color options for various industries.
Used as a Photosensitizer in Photocatalyst Production:
In the field of photocatalysis, 2-Hydroxyanthraquinone is employed as a photosensitizer, enhancing the efficiency of light-induced chemical reactions, which is crucial for environmental and energy-related applications.
Used as an Intermediate in Chemical Synthesis:
2-Hydroxyanthraquinone serves as an intermediate in the synthesis of other chemicals, contributing to the development of a diverse array of chemical products.
Used in Pharmaceutical Development:
2-HYDROXYANTHRAQUINONE is explored for its potential in pharmaceuticals, indicating its capacity to be a precursor or active ingredient in the formulation of new medications.
Used as an Antifungal and Antibacterial Agent:
2-Hydroxyanthraquinone is studied for its antifungal and antibacterial properties, suggesting its use in healthcare and sanitation to combat microbial infections.
Used in Antioxidant Formulations:
Given its antioxidant properties, 2-Hydroxyanthraquinone is considered for use in formulations aimed at treating or preventing oxidative stress-related disorders, highlighting its potential in the health and wellness sector.

InChI:InChI=1/C14H8O3/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7,15H

Synthetic route

2-aminoanthraquinone (117-79-3) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
Stage #1: 2-aminoanthraquinone With sodium nitrite at 20℃; for 3.5h; Stage #2: With water for 0.5h; Heating; Further stages.;	96%
Stage #1: 2-aminoanthraquinone With sulfuric acid; sodium nitrite Stage #2: With water Reflux;	90%
With sulfuric acid; sodium nitrite 0 deg C, 5 min then rt 30 min; 160 deg C, 12 h;	86%

9,10-phenanthrenequinone (84-65-1) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1,4-dihydroxy-9,10-anthracenedione (81-64-1)

Conditions	Yield
With sulfuric acid; boric acid for 5h; Product distribution; Mechanism; Irradiation; other time;	A n/a B 81%

9,10-phenanthrenequinone (84-65-1) → 2-hydroxy-9,10-anthraquinone (605-32-3) + anthracen-9(10H)-one (90-44-8) + 1-hydroxyanthraquinone (129-43-1) + bianthronyl (434-84-4)

Conditions	Yield
In sulfuric acid at 15℃; Product distribution; Mechanism; Quantum yield; Irradiation; N2;	A 80% B n/a C n/a D n/a
In sulfuric acid at 15℃; Irradiation;	A 80% B n/a C n/a D n/a

2-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-anthraquinone (867306-40-9) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran at 20℃; for 0.25h;	77%

2-carbomethoxy-9,10-anthraquinone (32114-48-0) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran at 20℃; for 0.25h;	77%

(anthracene)chromium tricarbonyl → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With boric acid tributyl ester; 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at -78℃; for 0.5h;	71%

9,10-phenanthrenequinone (84-65-1) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1-hydroxyanthraquinone (129-43-1) + 1,4-dihydroxy-9,10-anthracenedione (81-64-1)

Conditions	Yield
With sulfuric acid at 25℃; Irradiation;	A 70% B n/a C n/a
With sulfuric acid at 25℃; Irradiation; prolonged irradiation;	A n/a B 55% C 6%

9,10-phenanthrenequinone (84-65-1) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1-hydroxyanthraquinone (129-43-1)

Conditions	Yield
With air; sulfuric acid at 25℃; Irradiation;	A n/a B 60%
With air In water; isopropyl alcohol for 0.5h; Product distribution; Ambient temperature; Irradiation; other solvents: CHCl3 + water, dioxane + water, other reaction time: 15 min;
With air; sulfuric acid at 25℃; for 7h; Product distribution; Mechanism; Quantum yield; Irradiation; without air (argon), other time, other concentration of H2SO4, other temperature, other intensity of the light, other wavelenght;

sodium anthraquinone-2-sulfonate → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With sodium hydride; Benzaldoxime In tetrahydrofuran; vaseline; N,N-dimethyl acetamide at 60℃; for 3h; Inert atmosphere;	55%

2,3-bis(trimethylsilyloxy)-1,3-butadiene (31411-71-9) + [1,4]naphthoquinone (130-15-4) → 2-hydroxy-9,10-anthraquinone (605-32-3) + hystazarin (483-35-2)

Conditions	Yield
In toluene for 24h; Heating; Yields of byproduct given;	A 54% B n/a
In toluene for 24h; Heating; Yield given. Yields of byproduct given;

(4α,4aβ,9aβ)-9a-acetoxy-4a-chloro-4-methoxy-3,4,4a,9a-tetrahydroanthracene-2,9,10(1H)-trione → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With acetic acid; zinc at 20℃; for 3h; Reduction; aromatization;	54%

phthalic anhydride (85-44-9) + 4-bromo-phenol (106-41-2) → 3-bromo-1-hydroxy-9,10-anthraquinone (1116690-18-6) + 2-hydroxy-9,10-anthraquinone (605-32-3) + 1-hydroxyanthraquinone (129-43-1) + 2-hydroxy-3-bromoanthraquinone (72668-05-4) + 1-Bromo-4-hydroxyanthraquinone (6374-82-9)

Conditions	Yield
With aluminum (III) chloride; sodium chloride at 165 - 170℃; for 0.75h; Friedel-Crafts Acylation;	A 24% B 3% C 4% D 8% E 11%

tetrachloromethane (56-23-5) + 2-hydroxy-2,4a-dihydro-anthraquinone → 2-hydroxy-9,10-anthraquinone (605-32-3) + bianthrone (434-85-5)

Conditions	Yield
beim Erhitzen auf Temperaturen oberhalb des Schmelzpunkts;

phthalic anhydride (85-44-9) + phenol (108-95-2) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1-hydroxyanthraquinone (129-43-1)

Conditions	Yield
With sulfuric acid

1-methyl-4-nitrosobenzene (623-11-0) + 2-hydroxy-2,4a-dihydro-anthraquinone → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
at 215℃; und Leiten von Luft durch die Reaktionsloesung;

1,2-dihydroxy-9,10-anthracenedione (72-48-0) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With tin(ll) chloride

2-chloroanthracene-9,10-dione (131-09-9) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With ammonia at 215℃; unter Druck;

2-bromoanthracene-9,10-dione (572-83-8) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With potassium hydroxide

2-nitroanthraquinone (605-27-6) + potassium ethoxide (917-58-8) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 2-methoxy-9,10-anthraquinone (3274-20-2)

Conditions	Yield
With methanol

2-nitroanthraquinone (605-27-6) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 2-methoxy-9,10-anthraquinone (3274-20-2)

Conditions	Yield
With methanol; potassium ethoxide

2-sulfo-anthraquinone (84-48-0) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia / 190 °C 2: alcohol; nitrous acid / man kocht den erhaltenen Niederschlag mit Wasser View Scheme
With alkaline earth hydroxide

2-sulfo-anthraquinone (84-48-0) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With potassium hydroxide

2-acetoxyanthracene (16433-87-7) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With chromium(VI) oxide; acetic acid man verseift das entstandene Acetat durch Kochen mit waessr.Alkalien;

1-amino-2-hydroxy-9,10-anthracenedione (568-98-9) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With ethanol; cis-nitrous acid

2-hydroxy-anthrone (5452-86-8) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With sodium dichromate; acetic acid

2-hydroxy-9,10-dioxo-9,10-dihydro-anthracene-1-carboxylic acid (374705-59-6) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
at 237℃;
beim Erhitzen auf den Schmelzpunkt;

2-(3-hydroxy-benzoyl)-benzoic acid (634602-13-4) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1-hydroxyanthraquinone (129-43-1)

Conditions	Yield
With sulfuric acid at 100℃;

sodium anthraquinone-2-sulfonate (131-08-8) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With sodium hydroxide at 160 - 165℃; unter Druck; man loest die Schmelze in Wasser, faellt siedend heiss mit Salzsaeure, filtriert und behandelt den Niederschlag mit siedender Barytloesung, um Alizarin abzuscheiden; die erkaltete Barytloesung faellt man mit Salzsaeure;

9,10-phenanthrenequinone (84-65-1) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With ammonium persulfate; sulfuric acid
With quicklime; nitric acid; sodium sulfite at 190℃; Reagens 4:Wasser;unter Druck und Behandeln des Reaktionsproduktes mit Luft;

3-Carboxyphenol (99-06-9) + benzoic acid (65-85-0) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1-hydroxyanthraquinone (129-43-1)

Conditions	Yield
With sulfuric acid at 180 - 200℃;
With sulfuric acid; water at 180 - 200℃;

2-hydroxy-9,10-anthraquinone (605-32-3) + 3-[(6-bromohexyl)oxy]-9H-xanthen-9-one (473000-09-8) → 2-({6-[(9-oxo-9H-xanthen-3-yl)oxy]hexyl}oxy)anthracene-9,10-dione

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	96%

2-hydroxy-9,10-anthraquinone (605-32-3) → 2-hydroxyanthracene (613-14-9)

Conditions	Yield
With sodium tetrahydroborate; sodium carbonate In isopropyl alcohol for 0.333333h; Heating;	93%
With aluminium amalgam; ammoniaque In water for 1h; Heating;	76%
With phosphorus; hydrogen iodide

2-hydroxy-9,10-anthraquinone (605-32-3) + 2-Bromo-4'-phenylacetophenone (135-73-9) → 2-(2-(biphenyl-4-yl)-2-oxoethoxy)anthracene-9,10-dione

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-Bromo-4'-phenylacetophenone In N,N-dimethyl-formamide at 20℃; for 24h;	92%

1-bromo dodecane (112-29-8) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 2-n-decyloxy-9,10-anthraquinone

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 12h; Heating;	91%

2-hydroxy-9,10-anthraquinone (605-32-3) + methyl iodide (74-88-4) → 2-methoxy-9,10-anthraquinone (3274-20-2)

Conditions	Yield
With sodium hydride In tert-butyl methyl ether; N,N-dimethyl-formamide at 20℃; for 20h;	90%

2-hydroxy-9,10-anthraquinone (605-32-3) + 2-Bromo-4'-methoxyacetophenone (2632-13-5) → 2-(2-(4-methoxyphenyl)-2-oxoethoxy)anthracene-9,10-dione

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-Bromo-4'-methoxyacetophenone In N,N-dimethyl-formamide at 20℃; for 24h;	89%

2-hydroxy-9,10-anthraquinone (605-32-3) + 2-Bromo-2'-acetonaphthone (613-54-7) → 2-(2-(naphthalen-2-yl)-2-oxoethoxy)anthracene-9,10-dione

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-Bromo-2'-acetonaphthone In N,N-dimethyl-formamide at 20℃; for 24h;	89%

1-bromo-6-hexanol (4286-55-9) + 2-hydroxy-9,10-anthraquinone (605-32-3) → hydroxyhexyloxyanthraquinone

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	89%

1,4-dibromo-2-butene (6974-12-5) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 3-[(E)-4-bromobut-2-enyloxy]-9,10-anthraquinone

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate at 20℃; for 0.5h; Stage #2: 1,4-dibromo-2-butene for 4h; Reflux;	88%

2-hydroxy-9,10-anthraquinone (605-32-3) + 2-(chloromethyl)-5-(benzyloxy)-1-methylpyridin-4(1H)-one (586345-73-5) → 2-[(5-benzyloxy-1,4-dihydro-1-methyl-4-oxopyridin-2-yl)methoxy]anthrequinone (586345-84-8)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone Heating;	87%

2-hydroxy-9,10-anthraquinone (605-32-3) → 1,3-diiodo-2-hydroxyanthraquinone (117638-46-7)

Conditions	Yield
With iodine; sodium acetate; iodic acid In acetic acid for 0.833333h; Heating;	86%

2-hydroxy-9,10-anthraquinone (605-32-3) + 1-dodecylbromide (143-15-7) → 2-n-dodecyloxy-9,10-anthraquinone

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 12h; Heating;	86%

2-hydroxy-9,10-anthraquinone (605-32-3) + α-bromoacetophenone (70-11-1) → 2-(2-oxo-2-phenylethoxy)anthracene-9,10-dione

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: α-bromoacetophenone In N,N-dimethyl-formamide at 20℃; for 24h;	86%

1-Bromotetradecane (112-71-0) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 2-n-tetradecyloxyanthraquinone (1430074-42-2)

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-Bromotetradecane In N,N-dimethyl-formamide at 79.84℃; for 24h;	82%

2-hydroxy-9,10-anthraquinone (605-32-3) + 2-bromo-4'-fluoroacetophenone (403-29-2) → 2-(2-(4-fluorophenyl)-2-oxoethoxy)anthracene-9,10-dione

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-bromo-4'-fluoroacetophenone In N,N-dimethyl-formamide at 20℃; for 24h;	82%

pentadecyl bromide (629-72-1) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 2-n-pentadecyloxyanthraquinone (1430074-43-3)

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: pentadecyl bromide In N,N-dimethyl-formamide at 79.84℃; for 24h;	80%

1 ,6-dibromohexane (629-03-8) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 2-[(6-bromohexyl)oxy]anthracene-9,10-dione

Conditions	Yield
With potassium carbonate at 110℃; for 72h; Inert atmosphere;	79%

2-hydroxy-9,10-anthraquinone (605-32-3) → C14H7IO3

Conditions	Yield
With iodine In pyridine for 2h; Inert atmosphere;	78%

2-hydroxy-9,10-anthraquinone (605-32-3) + hexadecanyl bromide (112-82-3) → 2-n-hexadecyloxyanthraquinone

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: hexadecanyl bromide In N,N-dimethyl-formamide at 79.84℃; for 24h;	75%
With potassium carbonate In N,N-dimethyl-formamide for 12h; Heating;	41%

4-Nitrophthalonitrile (31643-49-9) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 4-[(9,10-dioxo-9,10-dihydroanthracen-2-yl)oxy]phthalonitrile

Conditions	Yield
With sodium carbonate In dimethyl sulfoxide at 45℃; for 48h;	75%

2-hydroxy-9,10-anthraquinone (605-32-3) + 1-Bromooctadecane (112-89-0) → 2-n-octadecyloxyanthraquinone (1430074-45-5)

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-Bromooctadecane In N,N-dimethyl-formamide at 79.84℃; for 24h;	73%

3,4-dihydro-2H-pyran (110-87-2) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 2-((tetrahydro-2H-pyran-2-yl)oxy)anthraquinone

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 17h;	72%

1-Bromoeicosane (4276-49-7) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 2-n-icosyloxyanthraquinone (1430074-46-6)

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-Bromoeicosane In N,N-dimethyl-formamide at 79.84℃; for 24h;	71%

Upstream product

• 56-23-5 tetrachloromethane 
• 85-44-9 phthalic anhydride 
• 108-95-2 phenol 
• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 
• 131-09-9 2-chloroanthracene-9,10-dione 
• 572-83-8 2-bromoanthracene-9,10-dione 
• 605-27-6 2-nitroanthraquinone 
• 917-58-8 potassium ethoxide 
• 84-48-0 2-sulfo-anthraquinone 
• 374705-59-6 2-hydroxy-9,10-dioxo-9,10-dihydro-anthracene-1-carboxylic acid 
• 131-08-8 sodium anthraquinone-2-sulfonate 
• 84-65-1 9,10-phenanthrenequinone 
• 99-06-9 3-Carboxyphenol 
• 65-85-0 benzoic acid 

Downstream Products

• 858011-51-5 N-(2-hydroxy-9,10-dioxo-9,10-dihydro-[1]anthrylmethyl)-phthalamic acid 
• 5449-65-0 2-hydroxy-10-anthrone 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 
• 120-12-7 anthracene 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 586397-71-9 2-[(5-benzyloxy-4-oxo-4H-pyran-2-yl)methoxy]anthraquinone 
• 2141-42-6 1,2,3,4-tetrahydroanthracene 
• 1079-71-6 1,2,3,4,5,6,7,8-octahydroanthracene 
• 1609021-27-3 2-hydroxy-3-(diphenylhydroxymethyl)anthracene 
• 1609021-34-2 2-methoxy-3-(diphenylhydroxymethyl)anthracene 
• 1609021-28-4 C₂₈H₂₂O₂ 
• 1609021-29-5 C₂₇H₁₉N₃O 
• 1609021-30-8 C₂₉H₂₁F₃O₂ 

Relevant academic research and scientific papers

Synthesis of bi- and tricyclic arylboronates via Cp*RuCl-catalyzed cycloaddition of α,ω-diynes with ethynylboronate

In the presence of 5-10 mol% Cp*RuCl(cod), 1,6- ana 1,7-diynes were allowed to react with an ethynylboronate at ambient temperature to give rise to bi- and tricyclic arylboronates in 64-93% isolated yields. The Royal Society of Chemistry 2005.

Photochemical Formation of Anthracene Quinone Methide Derivatives

Anthrols 2-7 were synthesized and their photochemical reactivity investigated by irradiations in aq CH3OH. Upon excitation with visible light (λ > 400 nm) in methanolic solutions, they undergo photodehydration or photodeamination and deliver methyl ethers, most probably via quinone methides (QMs), with methanolysis quantum efficiencies φR = 0.02-0.3. Photophysical properties of 2-7 were determined by steady-state fluorescence and time-correlated single photon counting. Generally, anthrols 2-7 are highly fluorescent in aprotic solvents (φF = 0.5-0.9), whereas in aqueous solutions the fluorescence is quenched due to excited-state proton transfer (ESPT) to solvent. The exception is amine 4 that undergoes excited-state intramolecular proton transfer (ESIPT) in neat CH3CN where photodeamination is probably coupled to ESIPT. Photodehydration may take place via ESIPT (or ESPT) that is coupled to dehydration or via a hitherto undisclosed pathway that involves photoionization and deprotonation of radical cation, followed by homolytic cleavage of the alcohol OH group from the phenoxyl radical. QMs were detected by laser flash photolysis and their reactivity with nucleophiles investigated. Biological investigation of 2-5 on human cancer cell lines showed enhancement of antiproliferative effect upon exposure of cells to irradiation by visible light, probably due to formation of electrophilic species such as QMs.

Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances

The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.

β-Hydroxylation of anthraquinone derivatives with benzaldehyde oxime as a source of hydroxyl group

Hydroxyanthraquinones are of significant interest due to their broad spectrum of biological activity, coloring properties and synthetic applications. Here, we describe a mild and convenient method for β-hydroxylation of anthraquinone derivatives that can be used during late stages of modifications. The scheme is based on the Miller-Loudon-Snyder reaction, which uses benzaldoxime as a source of a hydroxyl group. The influence of different leaving groups and neighboring substituents at the anthraquinone core on reaction rate and yield has been evaluated. A series of β-hydroxyanthraquinone derivatives was synthesized using the developed approach.

Palladium-Catalyzed Direct Acylation: One-Pot Relay Synthesis of Anthraquinones

A bis-acylation strategy to access functionalized anthraquinones via one-pot relay process, is presented. The first acylation was feasible under [Pd]-catalyzed intermolecular direct acylation reaction, while, the second acylation was accomplished by using intramolecular Friedel-Crafts acylation. Notably, benchtop aldehydes have been utilized as non-toxic acylation agents in the key [Pd]-catalyzed acylation.

Synthesis of asymmetrically disubstituted anthracenes

We have developed synthetic pathways toward differently substituted hydroxyanthracenes (anthrols) with the aim to investigate their photochemical reactivity in dehydration reactions. Although the syntheses of anthracenes substituted at positions 9,10 are well known, reports for the synthesis of anthracenes with different substitution patterns are scarce. Herein we review known and report novel synthetic pathways toward anthrols with substituents at 1,2-, 2,3-, and 2,6- positions. We present two synthetic approaches: (i) building of the anthracene tricyclic fused ring system from the appropriate benzene derivatives, and (ii) reduction of the corresponding anthraquinones. Reduction of 2-hydroxyanthracene-1-carbaldehyde to the corresponding alcohol yields rather unexpected 1,1′-methylenedianthracen-2-ol, whose proposed mechanism of formation is supported by experimental observations and calculations.

Synthesis of fluorescent diphenylanthracene-based calix[4]arene derivatives and their complexation with alkali metal cations

Two novel fluorescent calix[4]arenes comprising diphenylanthracene moiety at the lower rim were synthetized and their complexation with alkali metal cations in acetonitrile/dichloromethane and methanol/dichloromethane mixtures (φ = 0.5) was studied experimentally and by classical molecular dynamics and quantum chemical calculations. The monosubstituted calixarene derivative (L1) proved to be a poor cation receptor, whereas the ester-based macrocycle (L2) exhibited rather high affinity towards lithium, sodium and potassium cations, particularly in MeCN/CH2Cl2. All complexation reactions were enthalpically controlled, whereby the overall stability was the largest in the case of sodium complex. The computational investigations provided an additional insight into the complexation properties and structures of complex species. The molecular dynamics simulations indicated the occurrence of inclusion of solvent molecules in the calixarene hydrophobic cavity of the free and complexed ligand, which was found to significantly affect the complexation equilibria.

Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines

Damnacanthal and nordamnacanthal, two naturally occurring 9,10-anthraquinones, and their analogues were synthesized. Cytotoxic activity against five cancer cell lines was evaluated using MTT assay. 2-Bromomethyl-1,3-dimethoxyanthraquinone was found to display the highest activity against all cell lines with IC50 range of 2-8 μM. Structure-activity relationship (SAR) assessment was considered to rationalise the cytotoxic effect. Bromomethyl group at position C-2 of the anthraquinone was found to be important in exerting cytotoxic activity of this class of compounds. The presence of the flanking methoxyl or hydroxyl groups at C-1 and C-3 also contributes to this activity. Finally, the antioxidant effect of these compounds was evaluated. MTT assay was used to measure the cytotoxicity against different cancer cell lines. Antioxidant activity was measured by FTC and TBA methods. Only two anthraquinones, damnacanthal and nordamnacanthal, were found to be antioxidative.

Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues

Naturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC 50 = 5.70 ± 0.21 and 8.50 ± 1.18 μg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC 50 = 13.10 ± 1.02 and 14.80 ± 0.74), 1,3-dimethoxy-2-methylanthraquinone (4, IC50 = 9.40 ± 3.51 and 28.40 ± 2.33), and 1,3-dihydroxy-2-methylanthraquinone (3, IC 50 = 25.60 ± 0.42 and 28.40 ± 0.79) also exhibited moderate cytotoxicity against MCF-7 and K-562 cancer cell lines, respectively. Other structurally related compounds like 1,3-dihydroxyanthraquinone (13a, IC50 = 19.70 ± 0.35 and 14.50 ± 1.28), 1,3-dimethoxyanthraquinone (13b, IC50 = 6.50 ± 0.66 and 5.90 ± 0.95) were also showed good cytotoxicity. The target compound damnacanthal (1) was found to be the most cytotoxic against the MCF-7 and K-562 cancer cell lines, with IC50 values of 3.80 ± 0.57 and 5.50 ± 1.26, respectively. The structures of all compounds were elucidated with the help of detailed spectroscopic techniques.

Halophenol rearrangement in Lewis acid-catalyzed Friedel-Crafts conditions: Evidence of competitive initial protonation and acylation

Halogen rearrangement was observed during the Lewis acid-catalyzed Friedel-Crafts reaction of phthalic anhydride with bromophenols or bromoanisole. Further investigation revealed that 2-, 3-, and 4-bromophenols undergo rearrangement into other isomers under these reaction conditions. Product distribution from these reactions suggested that halogen rearrangement takes place during the s-complex intermediate of the condensation step. Furthermore, iodophenol undergoes hydrodeiodination rapidly rather than rearrangement, whereas chlorophenol does not undergo rearrangement at all. CSIRO 2008.