- Preparation method of diethyl ethoxy methylene malonate
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The invention discloses a preparation method of ethyoxyl methylene diethyl malonate, and the method comprises the following steps: taking diethyl malonate as a raw material and ethyl formate or carbon monoxide as an auxiliary material, introducing formyl under the action of a catalyst, and carrying out condensation reaction with alcohol under the catalysis of acid to obtain the product ethyoxyl methylene diethyl malonate, wherein ethyl formate can be replaced by CO, and the raw material cost is lower. The method has the advantages of simple operation, easily available raw materials, high conversion rate, safety, environmental protection and low cost, and can realize industrial production.
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Paragraph 0049-0050
(2021/06/06)
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- Design, Synthesis, and Dual Evaluation of Quinoline and Quinolinium Iodide Salt Derivatives as Potential Anticancer and Antibacterial Agents
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A series of novel quinoline and quinolinium iodide derivatives were designed and synthesized to discover potential anticancer and antibacterial agents. With regard to anticancer properties, in vitro cytotoxicities against three human cancer cell lines (A-549, HeLa and SGC-7901) were evaluated. The antibacterial properties against two strains, Escherichia coli (ATCC 29213) and Staphylococcus aureus (ATCC 8739), along with minimum inhibitory concentration (MIC) values were evaluated. The target alkyliodine substituted compounds exhibited significant antitumor and antibacterial activity, of which compound 8-((4-(benzyloxy)phenyl)amino)-7-(ethoxycarbonyl)-5-propyl-[1,3]dioxolo[4,5-g]quinolin-5-ium (12) was found to be the most potent derivative with IC50 values of 4.45±0.88, 4.74±0.42, 14.54±1.96, and 32.12±3.66 against A-549, HeLa, SGC-7901, and L-02 cells, respectively, stronger than the positive controls 5-FU and MTX. Furthermore, compound 12 had the most potent bacterial inhibitory activity. The MIC of this compound against both E. coli and S. aureus was 3.125 nmol ? mL?1, which was smaller than that against the reference agents amoxicillin and ciprofloxacin.
- Jin, Guofan,Li, Zhenwang,Qi, Xueyong,Sun, Xianyu,Xiao, Fuyan,Zhao, Lei
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- Optimization of activity localization of quinoline derivatives: Design, synthesis, and dual evaluation of biological activity for potential antitumor and antibacterial agents
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A novel of quarternary amine around a quinolinium iodide combined with even number alkyl chain were prepared in a several step in moderate yield starting from malonic ester and benzo[d][1,3]dioxol-5-amine. All of the active structure compounds were identified by nuclear magnetic resonance (NMR), such as 1H NMR, 13C NMR, infrared radiation (IR), high resolution mass spectrometry (HR-MS) and Carlo Erba Instruments CHNS-O EA1108 spectra analysis. With regard to the anticancer properties, the in vitro cytotoxicity against three human cancer cell lines (A-549, Hela and SGC-7901) were evaluated. The antibacterial properties against two human bacterial strains, Escherichia coli (ATCC 29213) and Staphylococcus aureus (ATCC 8739), along with minimum inhibitory concentration (MIC) values were evaluated. The target compounds, 5–12, exhibited significant antitumor and antibacterial activity, of which compound 12 was found to be the most potent derivative with IC50 values of 5.18 ± 0.64, 7.62 ± 1.05, 17.59 ± 0.41, and 54.45 ± 4.88 against A-549, Hela, SGC-7901, and L-02 cells, respectively, stronger than the positive control 5-FU and MTX. Furthermore, compound 12 had the most potent inhibitory activity. The MIC of this compound against Escherichia coli (ATCC 29213) and Staphylococcus aureus (ATCC 8739) was 3.125 nmol·mL?1, which was smaller than that of the reference agents, amoxicillin and ciprofloxacin.
- Jin, Guofan,Li, Zhenwang,Qi, Xueyong,Sun, Xianyu,Xiao, Fuyan
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- Green pepper flavor compound, preparation method thereof, food additive and green pepper flavor food
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The invention relates to a green pepper flavor compound, a preparation method thereof, a food additive and a green pepper flavor food. The green pepper flavor compound has the following structural formula, the green pepper flavor compound is a leaf alcohol ester compound, different from strong fresh grass leaf fragrance of leaf alcohol and grease gas of a traditional long-chain leaf alcohol estercompound, the green pepper flavor compound has obvious green pepper flavor different from leaf alcohol and obvious fragrance, and a new thought is provided for development of the leaf alcohol ester compound.
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Paragraph 0058; 0063-0065; 0076; 0081-0083; 0088; 0093-0095
(2020/07/21)
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- Preparation method and application of topramezone
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The invention discloses a preparation method and application of topramezone, and the preparation method comprises the following steps: taking 2-methylbenzaldehyde, a bromination reagent, a catalyst, hydroxylamine hydrochloride, an alkali, ethylene gas, a sulfonylation reagent and a preset solvent as reaction raw materials, and preparing 3-[3-bromo-methyl-6-(methylsulfonyl) phenyl]-4, 5-dihydroisoxazole through a first reaction process; taking diethyl malonate, triethyl orthoformate, nickel sulfate, monobasic saturated carboxylic acid, methylhydrazine, a hydrocarbon solvent, an ethanol solutionand hydrochloric acid as reaction raw materials, and carrying out a second reaction process to prepare 1-methyl-5-hydroxypyrazole; and taking the 3-[3-bromo-methyl-6-(methylsulfonyl) phenyl]-4, 5 dihydroisoxazole,-1-methyl-5-hydroxypyrazole, triethylamine, potassium carbonate, palladium chloride, triphenylphosphine, 1, 4-dioxane, water, a saturated NaHCO3 solution and a hydrochloric acid solutionas reaction raw materials, and carrying out a third reaction process to prepare the topramezone. The problems that a sulfur-containing intermediate can emit odor and the raw materials are difficult to obtain in the existing process are solved.
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Paragraph 0038-0039; 0054-0057
(2020/08/02)
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- Preparation method of diethyl ethoxymethylenemalonate
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The invention discloses a synthesis method for catalytically synthesizing diethyl ethoxymethylenemalonate by utilizing dual-cation liquid. The method takes triethyl orthoformate and diethyl malonate as raw materials, and ion liquid and acetic anhydride as catalysts of a reaction system, and comprises reaction at 125 DEG C for 8h. After reaction is finished, the ion liquid catalyst is filtered andrecycled; then the product diethyl ethoxymethylenemalonate is collected through decompressing and distilling filtrate. According to the method disclosed by the invention, the yield of the product synthesized by utilizing a novel dual-cation liquid catalyst is 95 percent or more, and the conversion rate is 100 percent; the ion liquid has good catalytic activity and has certain recycling performance; the yield of the reaction is obviously improved, and the reaction time is shortened.
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Paragraph 0015-0026
(2019/01/16)
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- Discovery of Benzimidazole–Quinolone Hybrids as New Cleaving Agents toward Drug-Resistant Pseudomonas aeruginosa DNA
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A series of benzimidazole–quinolone hybrids as new potential antimicrobial agents were designed and synthesized. Bioactive assays indicated that some of the prepared compounds exhibited potent antibacterial and antifungal activities. Notably, 2-fluorobenzyl derivative 5 b (ethyl 7-chloro-6-fluoro-1-[[1-[(2-fluorophenyl)methyl]benzimidazol-2-yl]methyl]-4-oxo-quinoline-3-carboxylate) showed remarkable antimicrobial activity against resistant Pseudomonas aeruginosa and Candida tropicalis isolated from infected patients. Active molecule 5 b could not only rapidly kill the tested strains, but also exhibit low toxicity toward Hep-2 cells. It was more difficult to trigger the development of bacterial resistance of P. aeruginosa against 5 b than that against norfloxacin. Molecular docking demonstrated that 5 b could effectively bind with topoisomerase IV–DNA complexes, and quantum chemical studies theoretically elucidated the good antimicrobial activity of compound 5 b. Preliminary experimental reaction mechanism exploration suggested that derivative 5 b could not intercalate into DNA isolated from drug-resistant P. aeruginosa, but was able to cleave DNA effectively, which might further block DNA replication to exert powerful bioactivities. In addition, compound 5 b is a promising antibacterial agent with membrane disruption abilities.
- Wang, Ya-Nan,Bheemanaboina, Rammohan R. Yadav,Gao, Wei-Wei,Kang, Jie,Cai, Gui-Xin,Zhou, Cheng-He
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p. 1004 - 1017
(2018/04/30)
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- Synthesis and biological evaluation of a class of quinolone triazoles as potential antimicrobial agents and their interactions with calf thymus DNA
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A novel series of quinolone triazoles were synthesized and characterized by IR, NMR, MS and HRMS spectra. All the newly prepared compounds were screened for their antimicrobial activities against seven bacteria and four fungi. Bioactive assay manifested that most of new compounds exhibited good or even stronger antibacterial and antifungal activities against the tested strains including multi-drug resistant MRSA in comparison with reference drugs Norfloxacin, Chloromycin and Fluconazole. The preliminary interactive investigations of compound 6b with calf thymus DNA by fluorescence and UV-vis spectroscopic methods revealed that compound 6b could effectively intercalate DNA to form compound 6b-DNA complex which might block DNA replication and thus exert its antimicrobial activities.
- Cui, Sheng-Feng,Ren, Yu,Zhang, Shao-Lin,Peng, Xin-Mei,Damu, Guri L.V.,Geng, Rong-Xia,Zhou, Cheng-He
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p. 3267 - 3272
(2013/06/27)
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- Synthesis and properties of water-soluble 2-aminomethylidene derivatives of 1,3-dicarbonyl compounds
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A series of [(2-dimethylamino)ethylamino]methylidene-1,3-dicarbonyl compounds was synthesized for the first time starting from the corresponding 2-ethoxymethylidene derivatives and N,N-dimethylethylenediamine. It was shown that further alkylation of aminomethylidene derivatives with methyl iodide occurs regioselectively at the tertiary nitrogen atom. Quaternization products obtained exhibit high corrosion inhibition of mild steel in hydrochloric acid medium.
- Bazhin,Kudyakova,Gorbunova,Burgart,Zapevalov,Saloutin
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p. 1330 - 1335
(2013/09/23)
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- PYRAZOLE DERIVATIVES AS CANNABINOID RECEPTOR LIGANDS, PHARMACEUTICAL COMPOSITIONS CONTAINING? THEM, AND PROCESSES FOR THEIR PREPARATION
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The present invention relates to cannabinoid receptor modulators of general formulas (I) and (II) prodrugs thereof, pharmaceutically acceptable salts thereof, and hydrates and solvates thereof, wherein the meaning of the substituents is as recited in the claims.
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Page/Page column 47
(2010/11/26)
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- NMR spectroscopic data of some 1-alkoxy-2,2-di(carbonyl, carboxyl, cyano)-substituted ethylenes
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The 1H-13C NMR shifts as well as 1H and 13C coupling constants of 14 alkoxymethylene malonic acid and acetoacetic acid derivatives and two alkoxymethylene acetylacetones are reported. The 17O NMR spectra have been recorded for six of them. The long-range coupling 3J(H-C=C-CR) has been used for determining the stereochemistry of the double bond. Copyright
- Hametner, Christian,Cernuchova, Petra,Milata, Viktor,Vo-Thanh, Giang,Loupy, Andre
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p. 171 - 173
(2007/10/03)
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- Thioxazinoquinolones as antiviral agents
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The present invention provides a compound of formula I These compounds are useful as antiviral agents, in particular, as agents against viruses of the herpes family.
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- Oxazinoquinolones useful for the treatment of viral infections
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The present invention provides a compound of formula I which is useful as antiviral agents, in particular, as agents against viruses of the herpes family.
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- N-cyclopropyl-2-difluoromethoxy-3-halogenoanilines and intermediates for the preparation thereof
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N-Cyclopropyl-2-difluoromethoxy-3-halogenoanilines which serve as important intermediates in the preparation of quinolonecarboxylic acids useful as synthetic antimicrobial agents from industrially inexpensive and easily available raw materials; and intermediates for the preparation thereof. Specifically, compounds represented by the general formula (1), (2) and (3), wherein X is halogeno; and Y is nitro or amino, (2) wherein X is halogeno; and R1is lower alkyl, (3) wherein X is halogeno; and R is hydrogen or —CH═C(CO2R2)2, R2being lower alkyl.
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- Synthesis and lipase-catalyzed asymmetric acetylation of 3-hydroxyl-2-hydroxymethylpropanal acetals
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Prochiral dialkylacetal derivatives of 3-hydroxy-2-hydroxymethylpropanal 6a-e were synthesized from the corresponding 2-substituted diethyl malonates 5a-e and subjected to asymmetric enzymatic acetylation. The diethyl malonates 5a-f were prepared from diethyl chloromethylenemalonate 3 by using either a one- or a two-step process. Asymmetric acetylation of 3-hydroxy-2-hydroxymethylpropanal diethyl acetal 6b with several enzymes was studied first, showing the highest enantiotopic selectivity with lipase from Pseudomonas fluorescens (PFL). Solvent effect was also investigated: the best selectivity was obtained in a mixture of hexane and diethyl ether. Furthermore, several other acetals 6a-e were also tested under the optimal acetylation conditions.
- Egri, Gabriella,Fogassy, Elemer,Novak, Lajos,Poppe, Laszlo
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p. 547 - 557
(2007/10/03)
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- Rhodium-catalyzed double carbonylation of diiodomethane in the presence of triethylorthoformate
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Catalytic double carbonylation of diiodomethane in triethylorthoformate in the presence of a homogeneous rhodium complex gives diethylmalonate in a fairly good yield.
- Cheong, Minserk,Kim, Mi-Na,Shim, Ji Yeon
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p. 253 - 255
(2007/10/03)
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- APPLICATION OF THE MNDO METHOD IN PLANNING THE SYNTHESIS OF Δ2-1,2,3-TRIAZOLES
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A study on the reactivity of several azides and dipolarophiles in cycloaddition reaction has been carried out and the results analyzed by MNDO calculations.In all cases it can be demonstrated that the reactivity is dependent not on the energy difference between the HOMO of one reactant and LUMO of the other but on the energy difference of corresponding chemically significant MOs.
- Juranic, Ivan,Husinec, Suren,Savic, Vladimir,Porter, Alexander E A.
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p. 411 - 417
(2007/10/02)
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- Process for the preparation of alkoxyalkylidenemalonic acid esters
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A process for the preparation of alkoxyalkylidenemalonic acid esters. The reaction is catalyzed by easily separable, insoluble aluminum silicates.
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- 9-(Substituted thio)-4H-pyrido[1,2,-A]pyrimidin-4-one derivatives
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9-(Substituted thio)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives of the formula: STR1 wherein n is 0 or 1, R is --COR1, --CONR4 R5 or --CH2 R6, R1 is C1 -C5 alkyl, C3 -C7 cycloalkyl, allythio, styryl, phenoxymethyl, thienylmethyl, C6 -C10 aryl optionally substituted, benzyl optionally substituted or 5- or 6-membered heterocyclic group optionally substituted, R2 and R3 each is hydrogen, C1 -C5 alkyl, carboxy, C2 -C5 alkoxycarbonyl or benzyloxycarbonyl optionally substituted, R4 and R5 each is hydrogen, C1 -C5 alkyl, C3 -C7 cycloalkyl or phenyl optionally substituted, and R8 is pyridyl or phenyl optionally substituted) being useful as antiulcer agents are provided through several routes.
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- 4-Piperidino-2-phenylquinolines
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Disclosed are compounds of the formula STR1 wherein: R1 and R2 may be either the same or different and each is hydrogen or lower alkyl; and wherein R3 and R4 may be either the same or different and each is hydrogen, halogen, or lower alkyl, with the proviso that R3 and R4 cannot both be hydrogen. These compounds are useful as anticonvulsant or anxiolytic agents.
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- A 13C AND 1H NMR STUDY OF FORMALDEHYDE REACTIONS WITH ACETALDEHYDE AND ACROLEIN. SYNTHESIS OF 2-(HYDROXYMETHYL)-1,3-PROPANEDIOL
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The 13C i 1H NMR spectra of various formaldehyde-acetaldehyde and formaldehyde-acrolein mixtures in buffered aqueous solutions were examined.Reaction intermediates and products were assayed including 3-hydroxypropanal, 3-hydroxy-2-(hydroxymethyl)propanal, pentaerythrose and pentaerythritol.Reaction mixtures were hydrogenated under various conditions to yield mixtures of 1,3-propanediol, pentaerythritol and 2-(hydroxymethyl)-1,3-propanediol.The latter compound was also prepared by an efficient new procedure from 3,3-diethoxy-2-(hydroxymethyl)-1-propanol.
- Nielsen, Arnold T.,Moore, Donald W.,Schuetze, Bryan D.
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p. 1393 - 1403
(2007/10/02)
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- Method of preparing alkoxymethylenemalonic acid esters
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Preparation of alkoxymethylene malonic acid ester of formula: STR1 wherein R and each R' is an alkyl group, by reaction of malonic acid diester and ortho formic acid triester. The reaction is performed in the presence of a carboxylic acid or a carboxylic acid anhydride and a Lewis acid. The ortho ester is initially present in amount of at least 1,4 mols per mole of the malonic acid ester starting material. Alcohol formed during the reaction is removed during the reaction.
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