cas 605-32-3, 2-HYDROXYANTHRAQUINONE | Articles data

Articles about 605-32-3Total 23 be found

Article title
Article abstract
Author
Journal number and time
Download

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.
Yamamoto, Yoshihiko,Hattori, Kozo,Ishii, Jun-Ichi,Nishiyama, Hisao,Itoh, Kenji
p. 4438 - 4440
(2005)
Read Online

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.
?kalamera, Dani,Mlinari?-Majerski, Kata,Martin Kleiner, Irena,Kralj, Marijeta,Oake, Jessy,Wan, Peter,Bohne, Cornelia,Basari?, Nikola
p. 6006 - 6021
(2017)
Read Online

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.
Li, Yuying,Guo, Fang,Chen, Tinggui,Zhang, Liwei,Wang, Zhuanhua,Su, Qiang,Feng, Liheng
(2020/09/04)

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.
Tikhomirov, Alexander S.,Ivanov, Ivan V.,Korolev, Alexander M.,Shchekotikhin, Andrey E.
(2019/09/30)

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.
Suchand, Basuli,Satyanarayana, Gedu
p. 769 - 779
(2019/01/23)

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.
?kalamera, ?ani,Veljkovi?, Jelena,Pti?ek, Lucija,Sambol, Matija,Mlinari?-Majerski, Kata,Basari?, Nikola
p. 5892 - 5899
(2017/09/09)

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.
Baki?, Marina Tranfi?,Leko, Katarina,Cindro, Nikola,Portada, Tomislav,Hrenar, Tomica,Frkanec, Leo,Horvat, Gordan,Po?ar, Josip,Tomi?i?, Vladislav
p. 711 - 725
(2018/05/07)

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.
Akhtar, Muhammad Nadeem,Zareen, Seema,Yeap, Swee Keong,Ho, Wan Yong,Lo, Kong Mun,Hasan, Aurangzeb,Alitheen, Noorjahan Banu
p. 10042 - 10055
(2013/09/23)

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.
Saha, Koushik,Lam, Kok Wai,Abas, Faridah,Sazali Hamzah,Stanslas, Johnson,Hui, Lim Siang,Lajis, Nordin H.
p. 2093 - 2104
(2013/07/26)

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.
Saha, Koushik,Lajis, Nordin H.,Abas, Faridah,Naji, Nabil Ali,Hamzah, A. Sazali,Shaari, Khozirah
p. 821 - 825
(2008/12/22)

Synthesis of arylboronates via Cp*RuCl-catalyzed cycloaddition of alkynylboronates
In the presence of 5-10 mol% Cp*RuCl(cod), 1,6- and 1,7-diynes were allowed to react with an ethynylboronate at ambient temperature to give rise to bicyclic arylboronates in 64-93% isolated yields. 1,6-Diynes bearing a boronate terminal also underwent cycloaddition with monoalkynes to give the corresponding bicyclic arylboronates.
Yamamoto, Yoshihiko,Hattori, Kozo,Ishii, Jun-ichi,Nishiyama, Hisao
p. 4294 - 4305
(2007/10/03)

Stable simple enols. Resolution of chiral 1-[9′-(2′-fluoroanthryl)]-2,2-dimesitylethenol. A different racemization mechanism for the enol and its acetate
Chiral 1-[9′-(2′-methoxyanthryl)]-2,2-dimesitylethenol (2), 1-[9′-(2′-fluoroanthryl)]-2,2-dimesitylethenol (3), and 1-[9′-(2′-fluoroanthryl)]-2,2-dimesitylvinyl acetate (4) were synthesized and their DNMR behavior in C6D5NO2 was studied. 3 and 4 were resolved on an amylose tris(3,5-dimethylphenylcarbamate) HPLC column to their enantiomers. Acetate 4 racemizes slowly in solution with ΔGe?, ΔHe?, and ΔSe? values of 26.2, 27.6 kcal mol-1, and 4.3 eu, respectively, as expected for a rotational ββ′-2-ring flip process in a vinyl propeller and the racemization is unaffected by added TFA, Et3N, and EtOD. Although 3 racemizes almost 350 times faster, the racemization is catalyzed by TFA and shows bell-shape catalysis by Et3N and a KIE in a partially deuteriated solvent. From this and the DNMR data, it is concluded that 3 does not racemize via a rotational ββ′-2-ring flip. Five nonflip routes are discussed for the racemization of 3, and it is concluded that only the one initiated by protonation at C1 does not contradict the experimental data. By analogy with the E/Z isomerization of the structurally related 2-(m-methoxymesityl)-1,2-dimesitylethenol 17, it is suggested that in the absence of added catalyst one or more enol molecule(s) catalyze the enantiomerization of another one. Only partial resolution was achieved for 2 and from the similarity of its behavior with that of 3, it is suggested that it racemizes by the same mechanism.
Rochlin, Elimelech,Rappoport, Zvi
p. 216 - 226
(2007/10/03)

Pathway of anthracene modification under simulated solar radiation
Exposure of polycyclic aromatic hydrocarbons (PAHs) to sunlight results in rapid structural photomodification generally via oxidation reactions. These PAH modification products are in many cases more toxic than their parent compounds. In this study, anthracene (ANT), a rapidly photooxidized PAH, was irradiated with simulated solar radiation (SSR, 100 μmol m-2 s- 1) in aqueous solution to examine the photomodification pathway. The photoproducts formed were identified by HPLC. The ANT product profile after 9 h in SSR was very complex, with more than 20 compounds detected. The photoproducts formed were anthraquinones, benzoic acids, benzaldehydes and phenols showing the process to be oxidative in nature. Some of the anthraquinones were themselves subject to photooxidation, and were thus intermediates in the product pathway. The kinetics of ANT photooxidation revealed a pseudo first-order reaction with a half-life of 2 h under the SSR source used. The kinetics of product formation allowed deduction of a probable photomodification pathway. This study indicates that PAH photooxidation products are likely to exist as complex, dynamically changing mixtures in PAH contaminated aquatic environments.
Mallakin, Ali,George Dixon,Greenberg, Bruce M.
p. 1435 - 1441
(2007/10/03)

Reaction of 2-acetoxy-3-chloro and 2,3-diacetoxy naphthoquinones with 1,3-dioxy and 1,1,3-trioxy butadienes
Reaction of 2-acetoxy-3-chloro naphthoquinones towards the 1,3-dioxy diene (2) and the 1,1,3-trioxy diene (9) was examined. The competing influence of the acetoxy and chloro substituents was assessed from the regiochemistry of the resulting Diels-Alder ch
Cameron, Donald W.
p. 1165 - 1171
(2007/10/03)

Different synthetic routes towards efficient organogelators: 2,3-substituted anthracenes
Three synthetic approaches towards 2,3-substituted anthracenes are reported and discussed in terms of selectivity and viability. This allowed us to introduce a variety of substituents as sidearms. Promising results have been found using a tandem Diels-Alder aromatization reaction using 2,2,3-dimethoxybuladiene 9 as a key intermediate. However, for multigram preparations the Friedel-Crafts approach is preferred.
Pozzo, Jean-Luc,Clavier, Gilles M.,Colomes, Michel,Bouas-Laurent, Henri
p. 6377 - 6390
(2007/10/03)

Metal Arene Complexes in Organic Synthesis. Hydroxylation, Trimethylsilylation, and Carbethoxylation of Some Polycyclic Aromatic Hydrocarbons Utilizing η6-Arene-Chromium Tricarbonyl Complexes
The deprotonation of polycyclic aromatic hydrocarbon (PAH) chromium tricarbonyl complexes (PAH = naphthalene, anthracene, phenanthrene, pyrene, fluoranthene) using an in situ technique where the PAH complex, the base (LiTMP or LDA), and the electrophile (trialkyl borate, trimethylsilyl chloride, or ethyl chloroformate) were placed in solution simultaneously resulted in hydroxylation, trimethylsilylation, or carbethoxylation of the PAH after oxidative workup where the regiochemistry was controlled by steric factors.As a result, substitution at positions of the PAHs not readily available by electrophilic substitution were obtained in some cases.Conditions minimizing isomer mixtures and factors affecting the regiochemistry and the scope of the reaction sequence were examined.
Morley, James A.,Woolsey, Neil F.
p. 6487 - 6495
(2007/10/02)

The photochemistry of 9,10-anthracenedione in sulfuric acid solution. The dependence of product yields on reaction conditions
Irradiation of a sulfuric acid solution of 9,10-anthracenedione with near-uv light generated 2-hydroxy-9,10-anthracenedione as the major product.In addition, the 1-hydroxy and polyhydroxy derivatives and the reduction products anthrone and bianthronyl were also formed.The yields of these minor products were markedly influenced by the concentrations of water and oxygen in the sulfuric acid.At low light intensities, oxygen quenched the efficient formation of the hydroxyanthracenediones and also oxidised the initial quinone reduction products.Photoreduction of the anthracenedione and photooxidation of anthrone occurred simultaneously in the solution.The reaction mechanism is more complex than previous studies indicated.
Broadbent, A. Douglas,Stewart, John M.
p. 1965 - 1969
(2007/10/02)

PHOTOCHEMICAL HYDROXYLATION OF ANTHRAQUINONE IN SULFURIC ACID
The photolysis of anthraquinone in sulfuric acid leads to hydroxylation of its ring with the preferential formation of 2-hydroxyanthraquinone in concentrated and 1-hydroxyanthraquinone in dilute sulfuric acid.The second hydroxy group only enters photochemically at position 4 of 1-hydroxyanthraquinone if the latter is activated by complex formation with boric acid.During photolysis in deaerated sulfuric acid the nitroanthraquinones are reduced photochemically to (hydroxyamino)anthraquinones; here 1-(hydroxyamino)anthraquinones with an unoccupied para position in the same condensed benzene ring undergo rearrangement under the reaction conditions to 1-amino-4-hydroxyanthraquinones.The main photochemical stage of hydroxylation in concentrated sulfuric acid is nucleophilic substitution of hydrogen in the monoprotonated anthraquinone by the HSO4(-) ion, while in dilute sulfuric acid it is electron transfer from water to anthraquinone.
Studzinskii, O.P.,El'tsov, A.V.
p. 1666 - 1673
(2007/10/02)

Regiospecific Reactions of Some Vinylogous Ketene Acetals with Haloquinones and Their Regioselective Formation by Dienolization
Regiospecific reactions of simple 1,3-bis(trimethylsiloxy)-1,3-butadienes with 2,5- and 2,6-dichlorobenzoquinones gave chloronaphthoquinones which, by applying the appropriate vinylketene acetal, provided various monomethyl ethers of isomeric polyhydroxyanthraquinones.The first total synthesis of macrosporin (27) was obtained in this way and the proposed structure for "cajaquinone" (28) found to be incorrect.Simple syntheses of 2-hydroxy-3-methylanthraquinone (16), phomarin (19), soranjidiol (22) and other naturally occuring quinones are also described.The dienolization of 1-methoxy-2,4-pentanedione in the presence of chlorotrimethylsilane gave either 1- or 5-methoxy-2,4-bis(trimethylsiloxy)-1,3-pentadiene, depending upon the reaction conditions.Both dienes react with haloquinones, giving regiospecific products, e.g., tetra-O-methylerythrolaccin (35).
Brisson, Clement,Brassard, Paul
p. 1810 - 1814
(2007/10/02)

Studies of Consecutive Reactions of Quinones in a Reversed Geometry Mass Spectrometer
Consecutive reactions involving the ejection of molecules of carbon monoxide from quinone systems have been studied.Using a reversed geometry double focusing mass spectrometer, the individual steps of a consecutive reaction may be separated into different field free regions.The structure of ions formed in the ion source may be compared with those formed from the fragmentation of metastable ions in a field free region by studying differences in the pattern of translational energies released when they break.In the case of anthraquinone it is found that two structures exist for the +. ion.Critical energy measurements strengthen this argument.Furthermore, 18O labelling has been used to distinguish between the loss of carbon monoxide from different positions on the molecular ion of 1-hydroxyanthraquinone.
Proctor, C. J.,Kralj, B.,Larka, E. A.,Porter, C. J.,Maquestiau, A.,Beynon, J. H.
p. 312 - 322
(2007/10/02)

PHOTOHYDROXYLATION OF ANTHRAQUINONE IN AQUEOUS MEDIA
Like the photolysis of anthraquinonesulfonic acids, the photolysis of anthraquinone in aerated aqueous organic media leads to isomeric monohydroxy derivatives with a preponderance of 2-hydroxyanthraquinone.It is assumed that during photohydroxylation electron transfer occurs from water (or OH- ion) to the anthraquinone in the T1n,?* state with subsequent attack on the unexcited substrate by the HO radical which forms.
Studzinskii, O. P.,El'tsov, A. V.
p. 1803 - 1805
(2007/10/02)

Photochemical Hydroxylation of Anthracene-9,10-dione in Sulphuric Acid Solution
Near u.v. irradiation of anthracene-9,10-dione in deoxygenated 96percent H2SO4 generates the sulphate ester of 2-hydroxyanthracene-9,10-dione in high yield along with the 1-hydroxy isomer and the novel reduction products anthracen-9(10H)-one and 9,9'-bianthracene-10,10'(9H,9'H)-dione; contrary to previous results, the product distribution and the rate of reaction are dependent upon the concentration of O2 in the solution.
Broadbent, A. Douglas,Stewart, John M.
p. 676 - 677
(2007/10/02)

Chemistry of Quinones. Part 6. The Selective Hydrolysis of α-Acetoxyanthraquinones and Related Compounds by Trifluoroacetic Acid Containing Small Amounts of Water
Acetoxy- or benzoyloxy-substituents adjacent to the carbonyl groups of anthraquinone, 1,4-naphthoquinone, naphthacene-5,12-quinone, benzophenone, and methyl benzoate are selectively converted into hydroxy-groups by treatment with trifluoroacetic acid containing small amounts of water.In the absence of water a reversible acidolysis occurs.Water reacts with the acylating agent, thus preventing the reverse reaction.Evidence is presented that the hydrolyses are of the AAC1 type.
Harrison, Charles R.,Hodge, Philip,Khan, Naeem
p. 1592 - 1594
(2007/10/02)