1072-84-0Relevant articles and documents
Heteroaryl hydroxycarbonylation: An efficient, robust, practically scalable approach using formyl acetate as the co source
Gadakh, Amol V.,Chikanna, Dinesh,Rindhe, Sahebrao S.,Karale, Bhausaheb K.
, p. 658 - 666 (2012)
A simple, efficient, regioselective, and scalable palladium-catalyzed hydroxycarbonylation of heteroaryl halides to corresponding carboxylic acids using acetic-formic anhydride in presence of Pd(OAc)2, dppf, and diisopropylethyl amine in dimethyl formamide at 80-90 °C in excellent yields. Taylor & Francis Group, LLC.
Oxidation of imidazole- and pyrazole-derived aldehydes by plant aldehyde dehydrogenases from the family 2 and 10
Fr?mmel, Jan,Kon?itíková, Radka,Kope?ny, David,Soural, Miroslav,?ebela, Marek
, p. 194 - 201 (2019)
Plant cytosolic aldehyde dehydrogenases from family 2 (ALDH2s, EC 1.2.1.3) are non-specific enzymes and participate for example in the metabolism of acetaldehyde or biosynthesis of phenylpropanoids. Plant aminoaldehyde dehydrogenases (AMADHs, ALDH10 family, EC 1.2.1.19) are broadly specific and play an important role in polyamine degradation or production of osmoprotectants. We have tested imidazole and pyrazole carbaldehydes and their alkyl-, allyl-, benzyl-, phenyl-, pyrimidinyl- or thienyl-derivatives as possible substrates of plant ALDH2 and ALDH10 enzymes. Imidazole represents a building block of histidine, histamine as well as certain alkaloids. It also appears in synthetic pharmaceuticals such as imidazole antifungals. Biological compounds containing pyrazole are rare (e.g. pyrazole-1-alanine and pyrazofurin antibiotics) but the ring is often found as a constituent of many synthetic drugs and pesticides. The aim was to evaluate whether aldehyde compounds based on azole heterocycles are oxidized by the enzymes, which would further support their expected role as detoxifying aldehyde scavengers. The analyzed imidazole and pyrazole carbaldehydes were only slowly converted by ALDH10s but well oxidized by cytosolic maize ALDH2 isoforms (particularly by ALDH2C1). In the latter case, the respective Km values were in the range of 10–2000 μmol l?1; the kcat values appeared mostly between 0.1 and 1.0 s?1. The carbaldehyde group at the position 4 of imidazole was oxidized faster than that at the position 2. Such a difference was not observed for pyrazole carbaldehydes. Aldehydes with an aromatic substituent on their heterocyclic ring were oxidized faster than those with an aliphatic substituent. The most efficient of the tested substrates were comparable to benzaldehyde and p-anisaldehyde known as the best aromatic aldehyde substrates of plant cytosolic ALDH2s in vitro.
Organic-inorganic hybrid materials constructed from inorganic lanthanide sulfate skeletons and organic 4,5-imidazoledicarboxylic acid
Sun, Yan-Qiong,Yang, Guo-Yu
, p. 3771 - 3781 (2007)
Five different types of the lanthanide sulfate-carboxylates family, [La2(SO4)(Himdc)2(H2O)2] 1, [Gd2(SO4)2(Himdc)(H2O) 3]·H2O 2, [Ln2(SO4) 2(Himdc)(H2O)3]·H2O (Ln = Gd 3a, Eu 3b), [Eu6Cu(SO4)6(Himdc) 4(H2O)14] 4, and [Ln(Himc)(SO 4)(H2O)] (Ln = Eu 5a, Gd 5b, Tb 5c, Dy 5d, Er 5e); H 2imc = 4-imidazolecarboxylic acid, H3imdc = 4,5-imidazoledicarboxylic acid) have been obtained by hydrothermal reactions of Ln2O3, transition metal sulfates and H3imdc at 170 °C and characterized by means of elemental analyses, IR, TG analysis, luminescence spectroscopy and single crystal X-ray diffraction. The 3D structure of 1 is constructed from alternately linkages of organic {La(Himdc)} layers and inorganic {La2O2(SO4)} layers, with the La atoms as hinges. 2 and 3a/3b both contain alternately arranged 1D left- and right-handed helical {Ln(imdc)} chains bridged by SO42- anions to form a 3D framework with 1D rectangle-like channels along the b axis. The structural differences of 2 and 3a/3b lie in the linkages of the SO 42- anions. Complex 4 consists of 2D tubular Eu-sulfate layers pillared by {Cu(Himdc)2} units to generate a 3D network. Complexes 5a-5e possess 2D bamboo-raft-like layer structures based on helical tubes. Interestingly, H2imc comes from the in-situ decarboxylation of H3imdc in the hydrothermal reactions. The luminescence properties of the complexes 3a, 4, 5a 5c, 5d were investigated in solid state at room temperature. The Royal Society of Chemistry.
Synthesis method of 1H-imidazole-4-carboxylic acid
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Paragraph 0022; 0029; 0036; 0043; 0050, (2018/05/16)
The invention discloses a synthesis method of 1H-imidazole-4-carboxylic acid. The method comprises steps as follows: (1) a hydrochloric acid solution is added to a reaction kettle, chromium trioxide is added under the stirring condition, the mixture is stirred uniformly and heated to 40-50 DEG C, pyridine is dropwise added, the mixture is stirred to react for 2-3 h after pyridine is dropwise added, PCC (pyridinium chlorochromate) is prepared, TiO2 is added, a dichloromethane solution of 4-methylimidazole is dropwise added under the stirring condition, the mixture is subjected to a reaction at40-50 DEG C for 3-4 h, then, filtration and centrifugation are performed, an organic layer is collected, reduced pressure distillation is performed, and 1H-imidazole-4-formaldehyde is prepared; (2) prepared 1H-imidazole-4-formaldehyde and dichloromethane are mixed, the obtained mixture is heated to 40-50 DEG C, KMnO4 is added, the mixture is mixed uniformly and stirred for a reaction for 3-4 h, filtration, reduced pressure distillation and recrystallization are performed, and 1H-imidazole-4-carboxylic acid is prepared. The synthesis method is simple to operate and mild in condition, fewer by-products are produced, the product purity is high and the product yield is higher.
Efficient synthesis method of pharmaceutical intermediate 1H-imidazole-4-formic acid
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Paragraph 0022; 0027; 0028; 0033; 0034; 0039; 0040; 0045, (2018/12/14)
The invention discloses an efficient synthesis method of a pharmaceutical intermediate 1H-imidazole-4-formic acid. The efficient synthesis method specifically comprises the following steps: firstly, preparing a titanium dioxide/titanium niobate compound catalyst; then taking 2-thiol-4-imidazole ethyl formate as a raw material; preparing 1H-imidazole-4-ethyl formate under the action of a hydrogen peroxide solution and a compound catalyst; then enabling the 1H-imidazole-4-ethyl formate to react with alkali liquid to prepare a target product. The efficient synthesis method disclosed by the invention has a simple reaction process and raw materials are cheap and easy to obtain; the prepared target product is simple to separate and the yield reaches 90 percent or more.
Preparation method of 1H-imidazole-4-carboxylic acid
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Paragraph 0018-0029, (2017/06/02)
The invention discloses a preparation method of 1H-imidazole-4-carboxylic acid. The preparation method includes dissolving 4-methylimidazole into an organic solvent, adding an oxidizing agent and a catalyst with stirring evenly, heating to 70-90 DEG C at a normal pressure, feeding oxygen, conducting refluxing reaction for 90-120 minutes and purifying to obtain the 1H-imidazole-4-carboxylic acid. The preparation method has the advantages that the preparation method is capable of preparing the 1H-imidazole-4-carboxylic acid through a one-step method, and is mild in reaction condition, high in conversion rate and simple in aftertreatment operation by the aid of a novel catalyst system, thereby having a promising industrial prospect.
Synthesis method of 4(5)-hydroxymethylimidazole
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Paragraph 0067; 0068; 0069; 0070; 0071, (2016/12/01)
The invention discloses a synthesis method of 4(5)-hydroxymethylimidazole. With 4,5-imidazoledicarboxylic acid as the raw material, decarboxylic reaction, esterification reaction and reduction reaction are conducted, manganese dioxide solid, ferric sulfate powder and a loaded Ni-Cu/SiO2 catalyst are added for catalytic reaction, reaction efficiency is improved, and reaction operation is simplified; meanwhile, the reaction process is improved, that is, the precipitation of 4(5)-imidazole carboxylic acid imidazole is promoted by adding sodium nitrate solid 5, the addition of concentrated sulfuric acid and a sodium hydroxide solution for neutralizing concentrated sulfuric acid is reduced by adding a catalyst, reaction consumption is reduced, reaction efficiency is improved, reaction operation is simplified, and high industrial popularization value is achieved.
Method for catalytically synthesizing 1H-imidazole-4-carboxylic acid through inorganic-salt composite catalyst
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Paragraph 0010; 0088; 0089, (2016/10/17)
The invention discloses a method for catalytically synthesizing 1H-imidazole-4-carboxylic acid through an inorganic-salt composite catalyst. Ethyl acetamidoacetate serves as a raw material and is enolized, cyclized, subjected to catalytic oxidation desulfurization and hydrolyzed to prepare the target compound; the method includes the three steps of preparing 2-sulfydryl-4-ethyl imidazolecarboxylate, preparing ethyl imidazole-4-carboxylate and preparing the 1H-imidazole-4-carboxylic acid; the inorganic-salt composite catalyst is prepared in the mode that barium sulfate, ferric nitrate and iron sulfate are compounded. The development method is a synthetic technology which is economical, environmentally friendly and easy to operate; the inorganic-salt composite catalyst is provided and added in an inorganic-salt solid mode, the cost of a raw material of the catalyst is low, a preparing method is environmentally friendly and simple, the selectivity of the catalytic effect of the catalyst is high, the yield is remarkably increased, by products are avoided, the catalyst can be recycled, and the quite high market promotion value is achieved.
Preparation method of 1H-imidazole-4-carboxylic acid
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Paragraph 0083; 0094; 0095; 0096; 0097, (2016/10/10)
The invention discloses a synthesis method of 1H-imidazole-4-carboxylic acid, and belongs to the field of chemical synthesis. A target compound is prepared through optimized enolization, cyclization, catalytic oxidation desulfurization and hydrolysis reaction with ethyl acetamidoacetate as the raw material, the yield of 1H-imidazole-4-carboxylic acid is increased, antimony butter is added as the catalyst for catalytic oxidation desulfurization reaction, the yield of 1H-imidazole-4-carboxylic acid is increased, energy consumption is lowered, and economic benefits are improved.
Aggrecanase-2 inhibitors based on the acylthiosemicarbazide zinc-binding group
Maingot, Lucie,Elbakali, Jamal,Dumont, Julie,Bosc, Damien,Cousaert, Nicolas,Urban, Agathe,Deglane, Gaelle,Villoutreix, Bruno,Nagase, Hideaki,Sperandio, Olivier,Leroux, Florence,Deprez, Benoit,Deprez-Poulain, Rebecca
, p. 244 - 261 (2013/10/01)
Osteoarthritis is a disabling disease characterized by the articular cartilage breakdown. Aggrecanases are potential therapeutic targets for the treatment of this pathology. At the starting point of this project, an acylthiosemicarbazide was discovered to inhibit aggrecanase-2. The acylthiosemicarbazide Zn binding group is also a convenient linker for library synthesis. A focused library of 920 analogs was thus prepared and screened to establish structure-activity relationships. The modification of the acylthiosemicarbazide was also explored. This strategy combining library design and discrete compounds synthesis yielded inhibitor 35, that is highly selective for aggrecanases over a panel of metalloproteases and inhibits the degradation of native fully glycosylated aggrecan. A docking study generated binding conformations explaining the structure-activity relationships.
