1125-55-9

Usage

Main properties

Chemical compound belonging to the class of quinones
Yellow, crystalline solid
Used as a chemical intermediate in organic compound synthesis
Exhibits cytotoxic and antitumor properties
Significant intermediate in the synthesis of therapeutic agents
Potentially hazardous and irritant substance

Color

yellow

Physical form

crystalline solid

Uses

chemical intermediate, biological activity (cytotoxic, antitumor)

Precautions

potentially hazardous, irritant

Importance

synthesis of therapeutic agents

Upstream product

• 64-19-7 acetic acid 
• 123-31-9 hydroquinone 
• 106-51-4 p-benzoquinone 
• 1201-38-3 2',5'-dimethoxyacetophenone 
• 490-78-8 2,5-Dihydroxyacetophenone 

Downstream Products

• 115148-11-3 cis-8-acetyl-3a,8b-dihydro-7-hydroxyfuro<3,2-b>benzo<2,1-d>furan-2(3H)-one 
• 99668-82-3 1,4-diacetoxy-2-acetyl-3-(1-methyl-2-propenyl)benzene 
• 99668-81-2 1,4-diacetoxy-2-acetyl-3-allylbenzene 
• 115271-09-5 3,4-Diacetyl-2,3-dihydro-2-methylbenzofuran-2,5-diol 
• 40815-79-0 2-acetyl-3-prop-2'-enyl-1,4-hydroquinone 
• 33537-83-6 2-Acetyl-3-ethoxy-1,4-benzochinon 
• 33539-21-8 6-ethoxy-2,5-dihydroxyacetophenone 
• 33537-86-9 2-Acetyl-3-allyloxy-[1,4]benzoquinone 
• 33539-24-1 1-(2-Allyloxy-3,6-dihydroxy-phenyl)-ethanone 
• 33537-84-7 2-Acetyl-3-isopropoxy-[1,4]benzoquinone 
• 33539-22-9 6-isopropoxy-2,5-dihydroxyacetophenone 
• 33537-87-0 2-Acetyl-3-benzyloxy-[1,4]benzoquinone 
• 33537-81-4 2-acetyl-3-benzyloxy-hydroquinone 
• 33537-85-8 2-Acetyl-3-butoxy-[1,4]benzoquinone 

Relevant academic research and scientific papers

Synthesis of 1-(Indol-2-yl)-phenoxazine hybrids from quinacetophenone precursors and their biological evaluation as DNA intercalating agents

An operationally simple reaction between quinacetophenone and aniline derivatives in the presence of triethylamine at room temperature afforded 1-(indol-2-yl)-phenoxazine hybrids in good yields. This unique transformation proceeds via sequential aza-Micha

Quinacetophenone: A simple precursor for synthesis of phenoxazines

Quinacetophenone is a versatile and easy accessible building block for synthesis of various biologically active heterocyclic compounds. The inherent chemical reactivity of quinacetophenone has been hitherto utilized to construct various privileged organic molecules such as chalcones, chromones, flavonoids, coumarins and azoles etc. Herein we present an operationally simple method of synthesis of phenoxazines from quinacetophenone and anilines that exploits the inherent chemical reactivity of quinacetophenone. ESI-MS was used as a tool to establish the most plausible reaction mechanism.

Synthesis of antiplatelet ortho-carbonyl hydroquinones with differential action on platelet aggregation stimulated by collagen or TRAP-6

Cardiovascular diseases are the leading cause of death in the world. Platelets have a major role in cardiovascular events as they bind to the damaged endothelium activating and forming thrombi. Although some hydroquinone scaffold-containing compounds have known antiplatelet activities, currently there is a lack of evidence on the antiplatelet activity of hydroquinones carrying electron attractor groups. In this work, we evaluate the antiplatelet effect of a series of ortho-carbonyl hydroquinone derivatives on cytotoxicity and function of human platelets, using collagen and thrombin receptor activator peptide 6 (TRAP-6) as agonists. Our structure-activity relationship study shows that gem-diethyl/methyl substitutions and the addition/modifications of the third ring of ortho-carbonyl hydroquinone scaffold influence on the selective index (IC50 TRAP-6/IC50 Collagen) and the inhibitory capacity of platelet aggregation. Compounds 3 and 8 inhibit agonist-induced platelet aggregation in a non-competitive manner with IC50 values of 1.77 ± 2.09 μM (collagen) and 11.88 ± 4.59 μM (TRAP-6), respectively and show no cytotoxicity. Both compounds do not affect intracellular calcium levels and mitochondrial bioenergetics. Consistently, they reduce the expression of P-selectin, activation of glycoprotein IIb/IIIa, and release of adenosine triphosphate and CD63 from platelet. Our findings may be used for further development of new drugs in platelet-related thrombosis diseases.

Silica-gel-supported ceric ammonium nitrate (CAN): A simple and efficient solid-supported reagent for oxidation of oxygenated aromatic compounds to quinones

A silica-gel-supported heterogeneous ceric ammonium nitrate (CAN) reagent has been developed for oxidizing oxygenated aromatics to quinones in nonaqueous media. The advantages of this procedure include excellent yields, mild reaction conditions, nonaqueous media, short reaction times, and easy product isolation. Copyright Taylor & Francis Group, LLC.

Synthesis of pyrrolo[3,2-b]benzofurans and pyrrolo[3,2-b]naphthofurans via addition of a silyloxypyrrole to activated quinones

The uncatalyzed reaction of N-(tert-butoxycarbonyl)-2-tert- butyldimethylsilyloxypyrrole 3 with 1,4-quinones bearing an electron withdrawing group at C-2 has been studied. Use of 1,4-quinones 4, 5 bearing an ester group at C-2 provided an efficient synthe

The synthesis of some fused pyrazolo-1,4-naphthoquinones

New fused pyrazolo-1,4-naphthoquinones were prepared from the reaction of hydrazines with 6-(4-methyl-3-pentenyl)-1,4-naphthoquinone. The reaction was extended to hydroxylamine to afford the corresponding isoxazolo-1,4-napthoquinone compound.

Experimental and Theoretical Justification for the Regiospecific Cycloaddition of Levopimaric Acid to 2-Acetyl- or 2-(Methoxycarbonyl)-1,4-Benzoquinone

New 4a-quinopimaric acid derivatives were synthesized via a Diels-Alder reaction of levopimaric acid with 2-acetyl- or 2-(methoxycarbonyl)-1,4-benzoquinone and were characterized using elemental analysis and NMR spectroscopy. Thermodynamic and activation

Cytotoxic-antineoplastic activity of acetyl derivatives of prenylnaphthohydroquinone

Several acetyl derivatives of prenylnaphthohydroquinone have been synthetised and evaluated for their cytotoxicity against A-549 human lung carcinoma and H-116 human colon carcinoma neoplastic cells. The IC50 values against A-549 are compared w

Assessing parameter suitability for the strength evaluation of intramolecular resonance assisted hydrogen bonding in O-carbonyl hydroquinones

Intramolecular hydrogen bond (IMHB) interactions have attracted considerable attention due to their central role in molecular structure, chemical reactivity, and interactions of biologically active molecules. Precise correlations of the strength of IMHB’s with experimental parameters are a key goal in order to model compounds for drug discovery. In this work, we carry out an experimental (NMR) and theoretical (DFT) study of the IMHB in a series of structurally similar o-carbonyl hydroquinones. Geometrical parameters, as well as Natural Bond Orbital (NBO) and Quantum Theory of Atoms in Molecules (QTAIM) parameters for IMHB were compared with experimental NMR data. Three DFT functionals were employed to calculated theoretical parameters: B3LYP, M06-2X, and ωB97XD. O . . . H distance is the most suitable geometrical parameter to distinguish among similar IMHBs. Second order stabilization energies ?Eij(2) from NBO analysis and hydrogen bond energy (EHB) obtained from QTAIM analysis also properly distinguishes the order in strength of the studied IMHB. ?Eij(2) from NBO give values for the IMHB below 30 kcal/mol, while EHB from QTAIM analysis give values above 30 kcal/mol. In all cases, the calculated parameters using ωB97XD give the best correlations with experimental1H-NMR chemical shifts for the IMHB, with R2 values around 0.89. Although the results show that these parameters correctly reflect the strength of the IMHB, when the weakest one is removed from the analysis, arguing experimental considerations, correlations improve significantly to values around 0.95 for R2

Half-wave potentials and in vitro cytotoxic evaluation of 3-acylated 2,5-bis(phenylamino)-1,4-benzoquinones on cancer cells

A broad range of 3-acyl-2,5-bis(phenylamino)-1,4-benzoquinones were synthesized and their voltammetric values, as well as in vitro cancer cell cytotoxicities, were assessed. The members of this series were prepared from acylbenzoquinones and phenylamines, in moderate to good yields (47-74%), through a procedure involving a sequence of two in situ regioselective oxidative amination reactions. The cyclic voltammograms of the aminoquinones exhibit two one-electron reduction waves to the corresponding radical-anion and dianion, and two quasi-reversible oxidation peaks. The first and second half-wave potential values (E1/2) of the members of the series were sensitive to the push-pull electronic effects of the substituents around the benzoquinone nucleus. The in vitro cytotoxic activities of the 3-acyl-2,5-bis(phenylamino)-1,4-benzoquinones against human cancer cells (bladder and prostate) and non-tumor human embryonic kidney cells were measured using the MTT colorimetric method. The substitution of both aniline groups, by either methoxy (electron donating effect) or fluorine (electron withdrawal effect), decreased the cytotoxicity in the aminoquinones. Among the members of the unsubstituted phenylamino series, two of the 18 compounds showed interesting anti-cancer activities. A preliminary assay, looking for changes in the expression of selected genes, was performed. In this context, the two compounds increased TNF gene expression, suggesting an association with an inflammatory-like response.