82-45-1Relevant articles and documents
Hydrogenation of 1-nitroanthraquinone to 1-aminoanthraquinone catalyzed by bimetallic cuptx nanoparticles
Yang, Chenchen,Wang, Aili,Yin, Hengbo
, p. 5906 - 5913 (2019)
Bimetallic CuPtx nanoparticles were prepared in ethanol solution by the wet chemical reduction method using Cu(NO3)2 and H2PtCl6 as starting materials, hydrazine hydrate as a reductant, and polyvinyl pyrrolidone as an organic modifier. The average particle sizes of Cu and Pt nanoparticles were 60 nm and 3 nm, respectively. The small-sized Pt nanoparticles were evenly anchored at the surfaces of large-sized Cu nanoparticles, forming Cu@Pt core-shell structured nanocomposites. In the bimetallic CuPtx nanoparticles, electron was transferred from platinum to copper species, which increased the selectivity of 1-aminoanthraquinone by suppressing the high hydrogenation activity of metallic platinum. The CuPt0.1 bimetallic nanoparticles exhibited higher catalytic activity for the hydrogenation of 1-nitroanthraquinone to 1-aminoanthraquinone than both monometallic Cu and Pt nanoparticles. Over the CuPt0.1 catalyst, the selectivity of 1-aminoanthraquinone was 99.3% at the 1-nitroanthraquinone conversion of 98.9%.
Efficient Selective Reduction of Aromatic Nitro Compounds Affording Aromatic Amines under CO/H2O Conditions Catalyzed by Amine-Added Rhodium-Carbonyl Complexes
Nomura, Kotohiro,Ishino, Masaru,Hazama, Motoo
, p. 2624 - 2628 (1991)
Remarkably high catalytic activities for the reduction of aromatic nitro compounds affording aromatic amines using CO (1 atm) and water at room temperature were exhibited by using amine-added rhodium carbonyl complexes (Rh(CO)2(acac), Rh4(CO)12, and Rh6(CO)16) in 2-methoxyethanol or diglyme (diethylene glycol dimethyl ether) containing a 5 equiv NaOH aqueous solution.The reduction proceeded not only with high catalytic activities, but also with remarkably high nitro-group selectivities, as exhibited in the case of 1-nitroanthraquinone affording 1-aminoanthraquinone, wit hout any other unsaturated groups, such as C=O, being reduced.The T.O.F. (turnovers/time) of 1776 mol-cat-1 h-1 (296 g-atom Rh-1 h-1) was attained for the reduction of p-nitroanisole yielding p-anisidine using Rh6(CO)16-1,8-bis(dimethylamino)-naphthalene catalyst.
Preparation method of 1-aminoanthraquinone
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Paragraph 0010, (2021/07/01)
A preparation method of 1-aminoanthraquinone comprises the following steps: by taking nickel carbonyl loaded by superparamagnetic nanoparticles as a catalyst and 1-nitroanthraquinone as a reaction substrate, adding a solvent, introducing hydrogen, and conducting reacting at 60-80 DEG C and 0.3-0.5 MPa for 2-8 hours; and applying a magnetic field to the reaction product to recover the catalyst, and performing post-treatment to obtain 1-aminoanthraquinone, wherein the mass of the catalyst is 0.003 times that of the 1-nitroanthraquinone, and the mass ratio of the 1-nitroanthraquinone to the solvent is 15:4. The 1-aminoanthraquinone synthesis process is simple and convenient, high in selectivity, environment-friendly, small in equipment investment and suitable for industrial production. The nickel carbonyl loaded by the superparamagnetic nanoparticles has moderate catalytic activity, nitryl can be selectively reduced, excessive reduction of carbonyl is avoided, the yield of the 1-aminoanthraquinone is high, and the catalyst can be collected and reused through an external magnetic field and can be repeatedly used for at least five times.
TARGETED BIFUNCTIONAL DEGRADERS
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Page/Page column 164; 165, (2021/04/17)
The present invention provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In another aspect, the present invention provides bifunctional compounds that can be used to promote or enhance degradation of certain autoantibodies. In certain embodiments, treatment or management of a disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein or the autoantibody in the subject. Thus, in certain embodiments, administration of a compound of the invention to the subject removes or reduces the circulation concentration of the circulating protein or the autoantibody, thus treating, ameliorating, or preventing the disease and/or disorder. In certain embodiments, the circulating protein is TNF.
Copper-catalyzed one-pot relay synthesis of anthraquinone based pyrimidine derivative as a probe for antioxidant and antidiabetic activity
Ahmad, Zaheer,Arshad, Uzma,Parveen, Shagufta,Rafiq, Naila,Shafiq, Nusrat,Zarren, Gul
, (2020/12/17)
Synthetic compounds have modernized the globe due to its vast applicable fields. Anthraquinones, as well as pyrimidine derivatives, are used as essential pharmacophores in the field of medicine. Maintenance of a green disease-free environment by using these derivatives is being acknowledged in developed as well as developing countries of the world. Considering the use of active catalysts in the synthesis of anthraquinone based derivatives are the era of concern for researchers due to their distinctive properties. Owing to the remarkable activities of anthraquinone and pyrimidine derivative, we synthesize compounds having both functionalities with the utilization of novel synergically active copper catalysts. This study explores the application of synthesized compounds using fast, ecofriendly and cost-effective approaches.1H and 13C NMR, antioxidant, antidiabetic, molecular docking and QSAR studies were used for characterization and evaluation of newly synthesized anthraquinone based pyrimidine derivatives. The result of these techniques shows that our desired compounds were successfully synthesized and have potent applications. Among all synthesized compounds, G2 and G3 showed a remarkable antioxidant activity with IC50 of 15.09 and 21.88 μg/ml respectively. While the compound G2 and G4 showed a strong inhibitory antidiabetic activity with the IC50 value of 24.23 and 28.94 μg/ml respectively. Furthermore, molecular docking results for both of the proteins assist the experimental data and confirms the different interactions between binding domains and substituent moieties. SAR study also relates to the experimental facts by giving us positive results of synthesized compounds. According to the QSAR study, G4 and G2 emerged as the most stable and most reactive compound among other compounds respectively. While MEP shows moderate to good nucleophilic and electrophilic reactivity of all four compounds.
Solvent-free, microwave assisted oxidation of alcohols with 4-hydroxypyridinium chlorochromate functionalized silica gel
AHMADI, Sayed Ali,GHALEHBANDI, Shermineh Sadat,GHAZANFARI, Dadkhoda,SHEIKHHOSSEINI, Enayatollah
, p. 283 - 289 (2020/10/06)
4-Hydroxypyridinium chlorochromate functionalized silica gel was found to be an efficient and reusable oxidant for the very fast oxidation of primary and secondary alcohols to the corresponding carbonyl compounds under solventfree conditions and microwave irradiation in excellent yields.
BIFUNCTIONAL SMALL MOLECULES TO TARGET THE SELECTIVE DEGRADATION OF CIRCULATING PROTEINS
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Page/Page column 32, (2019/11/04)
The present invention is directed to bifunctional small molecules which contain a circulating protein binding moiety (CPBM) linked through a linker group to a cellular receptor binding moiety (CRBM) which is a membrane receptor of degrading cell such as a hepatocyte or other degrading cell. In embodiments, the (CRBM) is a moiety which binds to asialoglycoprotein receptor (an asialoglycoprotein receptor binding moiety, or ASGPRBM) of a hepatocyte. In additional embodiments, the (CRBM) is a moiety which binds to a receptor of other cells which can degrade proteins, such as a LRP1, LDLR, FcyRI, FcRN, Transferrin or Macrophage Scavenger receptor. Pharmaceutical compositions based upon these bifunctional small molecules represent an additional aspect of the present invention. These compounds and/or compositions may be used to treat disease states and conditions by removing circulating proteins through degradation in the hepatocytes or macrophages of a patient or subject in need of therapy. Methods of treating disease states and/or conditions in which circulating proteins are associated with the disease state and/or condition are also described herein.
SMALL MOLECULE BASED ANTIBODY-RECRUITING COMPOUNDS FOR CANCER TREATMENT
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, (2017/03/08)
The present invention relates to chimeric (including bifunctional) compounds, compositions comprising those compounds and methods of treating cancer in a patient or subject, especially including metastatic cancer where cancer cells exhibit overexpression (heightened expression) of cell surface urokinase-type plasminogen activator receptor (urokinase receptor) compared to normal (non-cancerous) cells. The compounds bind to the urokinase-type plasminogen activator receptor (uPAR) on the surface of a cancer cell, including a metastatic cancer cell, and consequently recruit native antibodies of the patient or subject where the antibodies can selectively degrade and/or deactivate targeted cancer cells through antibody-dependent cellular phagocytosis and antibody-dependent cellular cytotoxicity (ADCC) and/or complement dependent cytotoxicity (CDC) against a large number and variety of cancers, thus providing cancer cell death and an inhibition of growth, elaboration and/or metastasis of the cancer, including remission and cure of the patient's cancer.
1-method for synthesizing amino-anthraquinone
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Paragraph 0035; 0036, (2017/03/14)
The invention relates to a synthetic method of 1-amino-anthraquinone. The mixture of sodium sulfide and sulfur is used as a reducing agent to generate 1-amino-anthraquinone through reduction, and consequently, the 1-amino-anthraquinone is obtained. The synthetic method provided by the technical solution of the invention is characterized in that the mixture of sodium sulfide and sulfur is used as the reducing agent, 150-230 kg of sulfur is added to industrial sodium sulfide per ton, the reducing capacity of the mixture is equivalent to that of 1.305-1.467 tons of industrial sodium sulfide and the reducing agent cost is reduced by 20-30%, the dosage of the sodium sulfide is greatly reduced in the new process and the cost of the reducing agent is reduced; in addition, the concentration of free alkali in a medium is reduced, the generation of hydrolysis side reaction is effectively controlled, the yield of reduction is improved by about 4% and the reducing waste residue is reduced; the obtained product is excellent in quality; the sulfur used in the new method is rich in source and low in cost; the reducing cost is reduced by about 1/4 and the yield of reduction is improved by about 4%; the synthetic method of 1-amino-anthraquinone has excellent environmental protection and economic benefit.
Continuous hydrogenation of a commercial aqueous phase synthesis of 1-amino-anthraquinone method
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Paragraph 0027-0034, (2017/03/14)
The invention discloses a method for synthesizing 1-amino anthraquinone via continuous hydrogenation of industrial water phases. 1-nitro anthraquinone and hydrogen are taken as raw materials. The method is characterized by comprising the following steps: adding water taken as a reaction solvent and a catalyst into a first reduction kettle, and respectively adding a 1-nitro anthraquinone alkali solution and the hydrogen to carry out a reduction reaction; enabling the reaction liquid to continuously and sequentially flow out from a liquid outlet when the reaction liquid in the reduction kettle reaches the liquid outlet and then flow into a second-stage reduction kettle and a third-stage reduction kettle which are connected in series with the first reduction kettle; carrying out catalyst separation after the reaction liquid flows out from a liquid outlet of the third-stage reduction kettle and flows into sedimentation and filtration equipment, and feeding a filtrate into an oxidation kettle; and carrying out oxidization to obtain a filter cake, namely the 1-amino anthraquinone. According to the method, the continuous hydrogenation reaction can be realized, so that the quality of the obtained 1-amino anthraquinone is improved, the yield of the obtained 1-amino anthraquinone is increased and the cost of the obtained 1-amino anthraquinone is lowered. In addition, the method is stable in production and is suitable for industrialized mass production. The environment-friendly water is taken as a reaction medium, so that the recycling of the catalyst and the solvent is realized, i.e., the discharge of waste residue, waste gas and the waste water is avoided. Therefore, the environment stress is lightened.
