- Phenoxyacetohydrazones against Trypanosoma cruzi
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Herein, we reported the design, synthesis, antitrypanosomal and cytotoxic evaluation of a new phenoxyacetohydrazones series. All derivatives were assayed against bloodstream trypomastigote forms of T. cruzi (Y strain) and intracellular amastigotes using the model of L-929 cells infected with trypomastigotes of the Tulahuen strain. Compound (E)-N′-(3.4-dihydroxybenzylidene)-2-phenoxyacetohydrazide (11) showed activity against trypomastigotes (IC50/24 h = 10.3 μM) equivalent to that of benznidazole and with selectivity index (SI) = 46. Against infected cultures, (E)-N′-((5-nitrofuran-2-yl) methylene)-2-phenoxyacetohydrazide (19) was active at the nanomolar range (IC50/96 h = 40 nM), being about 38-fold more active than the standard drug and with SI equal to 2500. Thus, derivatives 11 and 19 could be considered a good prototypes for the development of new candidates for Chagas disease therapy. [Figure not available: see fulltext.]
- Barbosa, Juliana M. C.,Capelini, Camila,Carvalho, Samir A.,Murta, Silvane M. F.,Sales Junior, Policarpo A.,Salom?o, Kelly,Wardell, James L.,Wardell, Solange M. S. V.,da Silva, Edson F.,de Souza, Kátia R.
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Read Online
- Host-guest complexation between simple pillar[5]arene and a new type of neutral guests
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Pillar[5]arenes are a new type of supramolecular hosts constructed from hydroquinone and their derivatives linked by methylene units. Searching new host-guest interaction between pillar[5]arenes and neutral guests are thus great interesting. Here, four neutral guests (AA0, AA2, AA4 and AA6) with both amino and amide groups were prepared from phenol by two steps. The host-guest interactions between perethylated pillar[5]arene (EtP5) and guest molecules were investigated in detail by various technologies, including 1H NMR, 13C NMR, 2D NOESY NMR, MS analysis and DFT calculation. We found that the guests (AA4 and AA6) with longer alkyl chain can form a stable inclusion complex with EtP5 through C–H···O, N–H···O, C–H···N and C–H···π interactions while shorter guests (AA0 and AA2) could not.
- Yan, Xin,Guo, Hao,Cen, Moupan,Huang, Youyou,Zhou, Lin,Zhu, Guohua,Yao, Yong
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Read Online
- Novel phenolic Mannich base derivatives: synthesis, bioactivity, molecular docking, and ADME-Tox Studies
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In this study, it was aimed to synthesize novel molecules containing potential biological active phenolic Mannich base moiety and evaluate the inhibition properties against α-glycosidase (α-Gly) and acetylcholinesterase (AChE). For this purpose, phenolic aldehydes (1–3) were synthesized from 4-hydroxy-3-methoxy benzaldehyde (vanillin) according to the Mannich Reaction. Five different carboxylic acid hydrazides (4a-e) were synthesized from esters obtained from carboxylic acids. Fifteen Schiff base derivatives (5a-e, 6a-e, and 7a-e) were synthesized from the condensation reaction of compounds 1–3 with 4a-e. In this work, a series of novel Schiff bases from Phenolic Mannich bases (5a-e, 6a-e, and 7a-e) were tested toward α-Gly and AChE enzymes. Compounds 5a-e, 6a-e, and 7a-e showed Kis in ranging of 341.36 ± 31.84–904.76 ± 93.56?nM on AChE and 176.27 ± 22.87—621.77 ± 69.98?nM on α-glycosidase. Finally, novel compounds were found using molecular docking method to calculate the biological activity of these bases against many enzymes. The enzymes used in these calculations are acetylcholinesterase and α-glycosidase, respectively. Molecule 6b is more effective and active than other molecules with a docking score parameter value of ? 8.77 against AChE enzyme and 6d is more effective and active than other molecules with a docking score parameter value of ? 4.94 against α-Gly enzyme. After calculating the biological activities of novel compounds, ADME/T analysis parameters were examined to calculate the future drug use properties.
- Tokal?, Feyzi Sinan,Taslimi, Parham,Demircio?lu, ?brahim Hakk?,?endil, K?v?lc?m,Tuzun, Burak,Gül?in, ?lhami
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p. 563 - 577
(2021/07/12)
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- Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors
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A series of aryloxyacetic acid derivatives were designed and synthesized as 4-hydoxyphenylpyruvate dioxygenase (HPPD) inhibitors. Preliminary bioassay results reveal that these derivatives are promising Arabidopsis thaliana HPPD (AtHPPD) inhibitors, in particular compounds I12 (Ki = 0.011 μM) and I23 (Ki = 0.012 μM), which exhibit similar activities to that of mesotrione, a commercial HPPD herbicide (Ki = 0.013 μM). Furthermore, the newly synthesized compounds show significant greenhouse herbicidal activities against tested weeds at dosages of 150 g ai/ha. In particular, II4 exhibited high herbicidal activity for pre-emergence treatment that was slightly better than that of mesotrione. In addition, compound II4 was safe for weed control in maize fields at a rate of 150 g ai/ha, and was identified as the most potent candidate for a novel HPPD inhibitor herbicide. The compounds described herein may provide useful guidance for the design of new HPPD inhibiting herbicides and their modification.
- Huang, Hao,Liu, Jian-Min,Shu, Lei,Wang, Man-Man,Yan, Yi-Le,Zhang, Da-Yong,Zhang, Jian-Qiu
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supporting information
p. 233 - 247
(2020/03/27)
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- Synthesis and anti-coronavirus activity of a series of 1-thia-4-azaspiro[4.5]decan-3-one derivatives
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A series of 1-thia-4-azaspiro[4.5]decan-3-ones bearing an amide group at C-4 and various substitutions at C-2 and C-8 were synthesized and evaluated against human coronavirus and influenza virus. Compounds 7m, 7n, 8k, 8l, 8m, 8n, and 8p were found to inhibit human coronavirus 229E replication. The most active compound was N-(2-methyl-8-tert-butyl-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl)-3-phenylpropanamide (8n), with an EC50 value of 5.5 μM, comparable to the known coronavirus inhibitor, (Z)-N-[3-[4-(4-bromophenyl)-4-hydroxypiperidin-1-yl]-3-oxo-1-phenylprop-1-en-2-yl]benzamide (K22). Compound 8n and structural analogs were devoid of anti-influenza virus activity, although their scaffold is shared with a previously discovered class of H3 hemagglutinin-specific influenza virus fusion inhibitors. These findings point to the 1-thia-4-azaspiro[4.5]decan-3-one scaffold as a versatile chemical structure with high relevance for antiviral drug development.
- Apayd?n, ?a?la Begüm,Cesur, Nesrin,Stevaert, Annelies,Naesens, Lieve,Cesur, Zafer
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- Synthesis and computer-aided analysis of the role of linker for novel ligands of the 5-HT6 serotonin receptor among substituted 1,3,5-triazinylpiperazines
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A series of 2-amino-4-(4-methylpiperazin-1-yl)-1,3,5-triazines was designed based on previously published 2-amino-4-benzyl-(4-methylpiperazin-1-yl)-1,3,5-triazines in order to evaluate the role of a linker between the triazine moiety and an aromatic substituent for the human serotonin 5-HT6 receptor affinity. As new linkers two carbon atoms (ethyl or ethenyl) or an oxyalkyl chain (methoxy, 2-ethoxy, 2-propoxy) were introduced. Affinities of the compounds for the 5-HT6R as the main target, and for the 5-HT1AR, 5-HT7R and D2R as competitive ones, were determined in the radioligand binding assays. Docking to the 5-HT6R homology model was performed to support SAR analysis. Results showed that the branching of the methoxyl linker increased affinity for the human 5-HT6R whereas an unsaturated bond within the linker dramatically reduced desirable activity. Both experimental and theoretical studies confirmed the previously postulated beneficial role of the aromatic size for interaction with the 5-HT6R. Thus, the largest naphthyl moiety yielded the highest activity. In particular, 4-(4-methylpiperazin-1-yl)-6-(1-(naphthalen-1-yloxy)ethyl)-1,3,5-triazin-2-amine (24), the most potent 5-HT6R agent found (Ki = 23 nM), can be a new lead structure for further search and development.
- ?a?ewska, Dorota,Kurczab, Rafa?,Wi?cek, Ma?gorzata,Sata?a, Grzegorz,Kie?-Kononowicz, Katarzyna,Handzlik, Jadwiga
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p. 319 - 325
(2018/12/11)
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- Design and Synthesis of Novel 4-Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action
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In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha-1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha-1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.
- Lei, Kang,Li, Pan,Yang, Xue-Fang,Wang, Shi-Ben,Wang, Xue-Kun,Hua, Xue-Wen,Sun, Bin,Ji, Lu-Sha,Xu, Xiao-Hua
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p. 10489 - 10497
(2019/10/02)
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- A benzene oxygen suo ester preparation method (by machine translation)
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The present invention provides a benzene oxygen suo ester preparation method, comprises the following steps: A) phenol compounds and alkaline hydroxide in dehydrating in organic solvent to form the salt, the salt of the phenol compound obtained; B) into the salt, adding chlorine suo ester, a condensation reaction, to obtain benzene oxygen suo ester and mixed solution of [...]; C) to 1 - 5 °C/min speed will be the system temperature dropped to 37 - 42 °C, and ultrasonic, chloride salt crystal grain becomes large, filtering to remove the [...]; the organic solvent is toluene, xylene, chlorobenzene, phenol, butanol and isobutanol in any mixture of the two. The invention in a mixed organic solvent in the dewatering of the phenol salt, in the dehydration process system always maintain a state are, to realize the continuous production, and the dewatering efficiency is high, the whole production process efficiency is high. And raw materials are easy, production cycle is short, low energy consumption, low production cost. And filtering to generate of [...], realizes the zero to produce zero emission of waste water. (by machine translation)
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Paragraph 0047; 0048; 0049; 0050; 0051; 0052; 0053-0058
(2019/01/08)
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- Preparation method of phenoxy carboxylic acid herbicide
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The invention provides a preparation method of a phenoxy carboxylic acid herbicide, comprising the following steps: S1, carrying out a condensation reaction between a phenolic compound and hydroxycarboxylic ester under the action of a catalyst so as to obtain phenoxycarboxylic ester, wherein the catalyst is one or more of protonic acid, solid acid and a supported catalyst; S2, carrying out 2- and/or 4- selecting chlorination reaction between phenoxycarboxylic ester and a chloridizing agent in the presence of a first catalyst and a second catalyst, so as to obtain chlorinated phenoxycarboxylicester, wherein the first catalyst is selected from Lewis acid, and the second catalyst is selected from a C5-C22 thioether compound, a C5-C22 thiazole compound, a C5-C22 isothiazole compound or a C5-C22 thiophene compound; and S3, carrying out an acidolysis reaction on chlorinated phenoxycarboxylic ester so as to obtain the phenoxy carboxylic acid herbicide. By the method, product quality and thelive environment of production can be improved, and ''three wastes (waste gas, waste water and industrial residue)'' are minimized.
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Paragraph 0083; 0084; 0111; 0112
(2019/01/08)
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- Preparation method of phenoxycarboxylic ester
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The invention provides a preparation method of phenoxycarboxylic ester, comprising the following step: a phenolic compound and hydroxycarboxylic ester react under the action of a catalyst to obtain phenoxycarboxylic ester, wherein the catalyst is one or more of protonic acid, solid acid and a supported catalyst. By using the phenolic compound and hydroxycarboxylic ester as the raw materials, the reaction is carried out in a chloride-free nonmetallic ion system, and generation of high salinity wastewater and metal chloride by-product is completely eradicated. Therefore, washing brine is saved,and wastewater quantity is greatly reduced. The wastewater quantity is reduced from original at least 25 tons to 82 kg for one ton of the product. According to the invention, the technological processis simplified, loss of active ingredients is reduced, yield of active ingredients is increased, and product purity is high. Meanwhile, the method is convenient for continuous production, production period is short, and raw materials are easily available. Therefore, the production cost is reduced.
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Paragraph 0031-0033; 0041-0044; 0051; 0052
(2019/01/08)
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- Selective conversion of primary amides to esters promoted by KHSO4
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Primary amides, either aliphatic or aromatic, are easily converted to the corresponding esters via reflux in lower primary alcohols in the presence of KHSO4. Secondary amides lead to complicated mixtures under analogous conditions, whereastertiary amides were inert. Use of isopropyl alcohol resulted inthe formation of product atslower rate and lower yieldalong withside products, whereas, use of tertiary alcoholsdid not give successful conversion andallyl and benzyl alcohol provided complex mixtures.
- Sattenapally, Narsimha,Sharma, Jhanvi,Hou, Yuqing
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p. 174 - 183
(2018/09/10)
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- Preparation method of phenoxyacetic ester
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The invention provides a preparation method of phenoxyacetic ester, wherein the preparation method includes the following steps: A) carrying out esterification reaction of acetic acid and alcohol to obtain acetic ester; B) introducing chlorine gas into acetic ester, and carrying out reaction to obtain chloroacetic ester; C) dehydrating a phenol compound and alkaline hydroxide into a salt in an organic solvent to obtain a salt of the phenol compound; D) after salt formation, mixing with chloracetic ester prepared in the step B), and carrying out condensation reaction to obtain phenoxyacetic ester, wherein the organic solvent is a mixture of any two kinds of toluene, xylene, chlorobenzene, phenol, butanol and isobutanol. The phenol is dehydrated into the salt in the mixed organic solvent, the system still maintains a uniform state in the dehydration process, continuous production is achieved, the dehydration efficiency is high and the efficiency of the whole production process is high. Moreover, the raw materials are easy to obtain, the production period is short, water is not needed in the reaction process, the energy consumption is low, the production cost is low, the yield of acetic acid is 99% or more, and the total yield of phenol can reach 99% or more.
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Paragraph 0052-0055; 0060-0063; 0064-0086
(2019/01/08)
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- A phenoxy ester preparation method (by machine translation)
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The invention provides a phenoxy ester preparation method, comprises the following steps: the phenol compounds with chlorine suo ester, acid, catalyst in the solvent mixed, one-pot synthesis to carry out the condensation reaction, to obtain the phenoxy carboxylic acid ester compounds; the solvent is DMF, DMSO, DMI and acetone in the one or more; wherein said catalyst is a quaternary ammonium salt or polyethylene glycol. The invention realizes a non-hydrous-phenoxy acetate, anhydrous outputs, anhydrous participation, truly zero waste water discharge, reduce the discharge of waste water, post filtering to salt can, without dehydration, low energy consumption, one-pot synthesis method ensures that the reaction procedure is simple, less equipment investment. And reduces [...] in a hydrolysis reaction, ɑ - chloro carboxylic acid hydrolysis, thereby reducing the consumption of ɑ - chloro carboxylic acid, at the same time effectively avoids the prior art machines or acid pure product of the solid-liquid separation as a result of the losses of the active ingredient, the extraction rate of the active ingredient, the product has high purity, high yield. (by machine translation)
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Paragraph 0029; 0030; 0031; 0032; 0033; 0034-0042; 0048-0052
(2019/01/08)
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- Preparation method of phenoxycarboxylic ester
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The invention provides a preparation method of phenoxycarboxylic ester, wherein the preparation method includes the following steps: A) dehydrating a phenol compound and alkaline hydroxide or carbonate into a salt in an organic solvent to obtain a salt of the phenol compound; B) adding chlorocarboxylic ester after salt formation, and carrying out condensation reaction to obtain phenoxycarboxylic ester, wherein the organic solvent is a mixture of any two of toluene, xylene, chlorobenzene, phenol, butanol and isobutanol. The phenol is dehydrated into the salt in the mixed organic solvent, the system still maintains a uniform state in the dehydration process, continuous production is achieved, the dehydration efficiency is high and the efficiency of the whole production process is high. Moreover, the raw materials are easy to obtain, the production cycle is short, the energy consumption is low, and the production cost is low.
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Paragraph 0043; 0044; 0045; 0046; 0047; 0048; 0049-0058
(2019/01/08)
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- Preparation method of phenoxycarboxylic ester compound
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The invention provides a preparation method of a phenoxycarboxylic ester compound, wherein the preparation method includes the steps: mixing a phenol compound represented by the formula (I) and halogenated carboxylic ester represented by the formula (II) with metal powder in an organic solvent, and carrying out heating reaction, to obtain a phenoxycarboxylic ester compound represented by the formula (III), wherein the metal powder is aluminum powder and/or magnesium powder, R is C1-C10 alkyl, R1 is straight-chain or branched-chain C1-C6 alkylene, R2 is C1-C10 alkyl, cycloalkyl or aryl, and X is halogen. Compared with the prior art, the phenol compound and the halogenated carboxylic ester are subjected to reaction in an anhydrous system, so the hydrolysis of the halogenated carboxylic esteris reduced, the production of high-salt wastewater is completely eradicated, dehydration is not needed in post-treatment, the treatment is simple, energy consumption is low, the loss of effective components caused by solid-liquid separation is avoided, the yield of the effective components is improved, the product has high purity and yield, and meanwhile, hydrogen gas produced by the reaction canalso be recycled.
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Paragraph 0035; 0036; 0037; 0038; 0039; 0040; 0041; 0042
(2019/01/08)
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- 3 - (2 - Acetyl) -4 - hydroxy -6 - methyl pyran -2 - ketone derivatives and its application
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The invention relates to a 3 - (2 - acetyl) - 4 - hydroxy - 6 - methyl-pyran - 2 - one derivatives and application. This kind of structure of the compound of the general formula (I), R, R1 Such as defined in the claims. In order to various phenol and chloroethyl acid methyl ester as the raw material, first of all by the substitution, hydrolysis, acylation reaction various phenoxy acetyl chloride, then with 4 - hydroxy - 6 - methyl-pyran - 2 - one condensation borate intermediate, finally through the Fries rearrangement reaction is obtained by the synthesis of 3 - (2 - acetyl) - 4 - hydroxy - 6 - methyl-pyran - 2 - one derivatives. The invention also relates to 3 - (2 - acetyl) - 4 - hydroxy - 6 - methyl-pyran - 2 - one derivatives in the herbicide application. Test results show that the compounds have good herbicidal activity, are a class of novel structure, application prospect of herbicide.
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Paragraph 0017-0018
(2018/10/11)
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- Preparation method of 2,4-dichlorophenoxyacetic acid and salt thereof
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The invention provides a preparation method of 2,4-dichlorophenoxyacetic acid and a salt thereof, wherein the preparation method includes the following steps: S1) carrying out a reaction of phenol andchloracetic ester under alkaline conditions to obtain phenoxyacetic ester; S2) carrying out selective chlorination reaction of the phenoxyacetic ester with a chlorinating agent under the action of acatalyst A and a catalyst B to obtain 2,4-dichlorophenoxyacetic ester, wherein the catalyst A is Lewis acid, and the catalyst B is C5-22 thioethers, thiazoles, isothiazoles and thiophenes or halogenated derivatives thereof; and S3) carrying out hydrolysis reaction of 2,4-dichlorophenoxyacetic ester under acidic conditions to obtain 2,4-dichlorophenoxyacetic acid; or after 2,4-dichlorophenoxyaceticester is obtained, carrying out an alkaline hydrolysis reaction with an alkaline compound to obtain 2,4-dichlorophenoxyacetate. The production and use of 2,4-dichlorophenol with unpleasant odor are avoided, the production of dioxins is eliminated, the yield of products is improved, and the output of three wastes is greatly reduced.
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Paragraph 0085; 0086
(2019/01/06)
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- Preparation method of phenoxycarboxylate herbicide
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The invention provides a preparation method of a phenoxycarboxylate herbicide, wherein the preparation method includes the steps: S1, carrying out condensation reaction of phenol or o-cresol with chlorocarboxylic ester under the action of alkaline substances to obtain phenoxycarboxylic ester, wherein chlorocarboxylic ester has the general formula of ClR1COOR, R1 is C1-3 alkylene or alkylidene, R is C1-10 alkyl of or C3-10 cycloalkyl; and S2, under the action of a first catalyst and a second catalyst, carrying out selective chlorination of the phenoxycarboxylic ester with a chlorinating agent to obtain the chlorophenoxycarboxylic ester represented by the formula I, R3 is H, Cl or CH3, the first catalyst is selected from Lewis acid, and the second catalyst is selected from C5-22 thioether, thiazole, isothiazole or thiophene compounds; and S3, mixing chlorophenoxycarboxylic ester with an alkaline compound, and carrying out alkaline hydrolysis to obtain the phenoxycarboxylate herbicide. The preparation method can improve the product quality and production operation environment, and has low quantity of three wastes.
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Paragraph 0060; 0064; 0068; 0072; 0100; 0111; 0112
(2019/01/08)
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- Preparation method of phenoxycarboxylic acid choline salt
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The invention provides a preparation method of a phenoxycarboxylic acid choline salt, wherein the preparation method includes the steps: S1, carrying out condensation reaction of phenol or o-cresol with chlorocarboxylic ester in the presence of alkaline substances to obtain phenoxycarboxylic ester; S2, carrying out selective chlorination of the phenoxycarboxylic ester with a chlorinating agent inthe presence of a first catalyst and a second catalyst to obtain chlorobenzoxycarboxylic ester; and S3, after reaction of trimethylamine with ethylene oxide, adding the chlorophenoxycarboxylic acid ester, and carrying out alkaline hydrolysis reaction to obtain the phenoxycarboxylic acid choline salt. Compared with a conventional synthesis technology, the preparation method effectively avoids the production and use of chlorophenols with unpleasant odor, radically eliminates the production of highly toxic dioxins, and greatly improves the product quality and the operation environment of the production site; with phenol as the raw material, through condensation, selective chlorination and alkaline hydrolysis, the high-quality phenoxycarboxylic acid choline salt is obtained, the loss of effective ingredients is effectively avoided and the yield of the product is increased.
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Paragraph 0059-0060; 0104; 0108; 0112
(2019/01/08)
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- A phenoxy carboxylic acid ester herbicide preparation method (by machine translation)
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The invention provides a phenoxy carboxylic acid ester herbicide preparation method, including: S1, phenol in the presence of alkaline substance with the chlorinated carboxylic acid ester condensation reaction, phenoxy carboxylic acid ester obtained; the ClR states the chloro- carboxylic acid ester of the general formula1 COOR, R1 Is C1 - 3 alkylene or alkylidene, R is C1 - 10 alkyl or C3 - 10 cycloalkyl; S2, the [...] ester in the 1st and 2nd catalyst the presence of a catalyst, with the chlorinating agent to carry out the selective chlorination of, get [...] ester; the Lewis acid catalyst is selected from the 1st, the 2nd catalyst is C5 - 22 of the thioether, thiazole, thiophene compounds or different benzisothiazoles; S3, will the [...] ester with an alcohol reaction, as shown in formula I phenoxy carboxylic acid ester herbicide; R3 Is H, Cl or CH3 , R ' is a C4 - 20 alkyl or cycloalkyl. This invention can improve the product quality and the production environment, three waste low. (by machine translation)
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Paragraph 0066; 0067; 0071; 0075; 0079; 0106; 0107
(2019/01/08)
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- A phenoxy carboxylic acid herbicide preparation method (by machine translation)
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The invention provides a phenoxy carboxylic acid herbicide preparation method, including: S1, will be [...], alkaline substance mixed with the chlorinated carboxylic acid ester, in the one-pot condensation reaction in anhydrous system, phenoxy carboxylic acid ester obtained; the ClR states the chloro- carboxylic acid ester of the formula is1 COOR, R1 Is C1 - 3 alkylene or alkylidene, R is C1 - 10 alkyl or C3 - 10 cycloalkyl; S2, the [...] ester in the 1st and 2nd catalyst under the action of a catalyst, with the chlorinating agent to carry out the selective chlorination of, get [...] ester; the Lewis acid catalyst is selected from 1st, 2nd catalyst is C5 - 22 of the thioether compound, thiazole compound, isothiazole compound or thiophene compound; S3, will the [...] ester to acid hydrolysis reaction, as shown in formula I phenoxy carboxylic acid herbicide, R3 Is H, Cl or CH3 . This invention can improve the quality of the products and the operating environment of production, three waste low. (by machine translation)
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Page/Page column 9; 10; 12
(2019/01/08)
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- Preparation method of 2,4-dichlorophenoxyacetic ester
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The invention provides a preparation method of 2,4-dichlorophenoxyacetic ester, wherein the preparation method includes the following steps: S1) carrying out a reaction of phenol and methyl chloroacetate under alkaline conditions to obtain methyl phenoxyacetate; S2) carrying out selective chlorination reaction of methyl phenoxyacetate with a chlorinating agent under the action of a catalyst A anda catalyst B to obtain 2,4-methyl dichlorophenoxyacetate, wherein the catalyst A is Lewis acid, and the catalyst B is C5-22 thioethers, thiazoles, isothiazoles and thiophenes or halogenated derivatives thereof; and S3) carrying out transesterification reaction of 2,4-methyl dichlorophenoxyacetate and alcohol under the action of a catalyst, to obtain 2,4-dichlorophenoxyacetic ester, wherein the alcohol is C2-20 alcohol. The selective chlorination reaction is carried out with methyl phenoxyacetate as a raw material, the selectivity of the reaction is improved, the loss of effective components isavoided, the yield of the effective components is greatly improved, and the three-waste treatment capacity, the three-waste treatment difficulty and the treatment cost are reduced.
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Paragraph 0070; 0071; 0076; 0077; 0080; 0081; 0084; 0085
(2019/01/08)
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- Preparation method of phenoxycarboxylic acid herbicide
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The invention provides a preparation method of a phenoxycarboxylic acid herbicide, wherein the preparation method includes the steps: S1, carrying out reaction of anhydrous phenol with an active metalto form phenoxide, and carrying out condensation reaction of the phenoxide with chlorocarboxylic ester to obtain phenoxycarboxylic ester, wherein the chlorocarboxylic ester has the general formula ofClR1COOR, R1 is C1-3 alkylene or alkylidene, and R is C1-10 alkyl or C3-10 of cycloalkyl; S2, carrying out selective chlorination of the phenoxycarboxylic ester with a chlorinating agent in the presence of a first catalyst and a second catalyst to obtain chlorobenzoxycarboxylic ester, wherein the first catalyst is selected from Lewis acid, and the second catalyst is C5-22 thioether, thiazole, isothiazole or thiophene compounds; and S3, carrying out acidolysis reaction of chlorobenzoxycarboxylic ester to obtain the phenoxycarboxylic acid herbicide represented by the formula I, wherein R3 is H,Cl or CH3. The preparation method can improve the product quality and the operation environment of the production site, and has low quantity of three wastes.
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Page/Page column 9; 10; 12
(2019/01/08)
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- Preparation method of phenoxycarboxylic acid herbicide
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The invention provides a preparation method of a phenoxycarboxylic acid herbicide, wherein the preparation method includes the steps: S1, carrying out condensation reaction of phenol or o-cresol withchlorocarboxylic ester under the action of an alkaline substance to obtain phenoxycarboxylic ester, wherein the chlorocarboxylic ester has the general formula of ClR1COOR, R1 is C1-3 alkylene or alkylidene, and R is C1-10 alkyl or C3-10 cycloalkyl; S2, carrying out selective chlorination of phenoxycarboxylic ester with a chlorinating agent under the action of a first catalyst and a second catalyst, to obtain chlorobenzoxycarboxylic ester, wherein the first catalyst is selected from Lewis acid, the second catalyst is C5-22 thioether compounds, thiazole compounds, isothiazole compounds or thiophene compounds; and S3, carrying out acidolysis reaction of chlorobenzoxycarboxylic ester, to obtain the phenoxycarboxylic acid herbicide represented by the formula I, wherein R3 is H, Cl or CH3. The preparation method can improve the product quality and the operation environment of a production site, and has low quantity of three wastes.
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Paragraph 0066; 0067; 0070; 0071; 0074; 0075; 0078; 0079
(2019/01/08)
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- Highly effective C-C bond cleavage of lignin model compounds
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A highly effective method is developed for the C-C bond cleavage of lignin model compounds. The inert Cα-Cβ or Cα-Cphenyl bond of oxidized lignin model compounds was successfully converted to an active ester bond through the classic organic name reaction, Baeyer-Villiger (BV) oxidation, and thus acetal esters and aryl esters were produced in high yields (up to 99%) at room temperature. Next, K2CO3 catalyzed the alcoholysis of the resulting ester products at 45 °C, affording various useful chemical platforms in excellent yields (up to 99%), such as phenols and multifunctional esters. This method uses commercially available reagents, is transition-metal free and simple, but highly effective, and involves mild reaction conditions.
- Wang, Yinling,Wang, Qianyi,He, Jianghua,Zhang, Yuetao
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supporting information
p. 3135 - 3141
(2017/07/24)
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- Synthesis and antibacterial evaluation of new sulfone derivatives containing 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole moiety
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Sulfones are one of the most important classes of agricultural fungicides. To discover new lead compounds with high antibacterial activity, a series of new sulfone derivatives were designed and synthesized by introducing the aroxymethyl moiety into the scaffold of 1,3,4-oxadiazole/thiadiazole sulfones. Antibacterial activities against three phytopathogens (Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, Xanthomonas axonopodis pv. citri.) were assayed in vitro. As compared to the control of commercial fungicides and some reported sulfone fungicides, seven compounds 5I-1-5I-7 exerted remarkably higher activities with EC50 values ranging from 0.45-1.86 μg/mL against X. oryzae and 1.97-20.15 μg/mL against R. solanacearum. Exhilaratingly, 5I-1, 5I-2 and 5I-4 displayed significant in vivo activity against X. oryzae with protective effect of 90.4%, 77.7%, and 81.1% at 200 μg/mL, respectively, much higher than that exhibited by Bismerthiazol (25.6%) and Thiadiazole-copper (32.0%). And the differential phytotoxicity of active derivatives was preliminarily checked. The results demonstrated that derivative of 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole sulfone can serve as potential alternative bactericides for the management of plant bacterial diseases.
- Su, Shihu,Zhou, Xia,Liao, Guoping,Qi, Puying,Jin, Linhong
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- Synthesis and molecular structures of 1-hydroxyethyl-2-(p-substituted) phenoxymethyl benzimidazoles
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Five novel 1-hydroxyethyl-2-(p-substituted) phenoxymethyl benzimidazoles were synthesized by a three-step route. Under microwave irradiation, the p-substituted phenols were firstly O-carboxymethylated to prepare the corresponding p-substituted phenoxymethyl acids, which then reacted with o-phenylendiamine to get the key intermediates 2-(p-substituted) phenoxymethyl benzimidazole. Finally, the solid-liquid phase transfer catalysis method, where tetrabutyl ammonium bromide (TBAB) was used as the catalyst, was applied to synthesize the target compounds c1-c5 by the N-hydroxyethylation reaction with 2-chloroethyl alcohol. The structures of the obtained compounds were well characterized and confirmed by elemental analysis, MS, IR, 1H NMR, 13C NMR and single-crystal X-ray diffraction analysis.
- Wu, Jiacheng,Zhao, Li,Zhao, Changqing,Wang, Zhiyuan,Gu, Haibin,Chen, Wuyong
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p. 974 - 980
(2016/11/22)
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- Bis azide-triphenylphosphine as a reagent for esterification at room temperature
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Modified Staudinger reaction is a well-established reaction for the amide synthesis from organic azides and carboxylic acids in the presence of phosphorous reagents. In contrary to this, it is notable that bis azide in the presence of triethylphosphite or trimethylphosphite does not afford the expected bis amides but affords the ethyl or methyl esters of the carboxylic acids respectively. This serendipitous observation when further investigated results in the discovery of bis azide-triphenylphosphine as an efficient reagent for esterification at room temperature.
- Dinesh, Murugan,Archana, Sivasubramaniyan,Ranganathan, Raja,Sathishkumar, Murugan,Ponnuswamy, Alagusundaram
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supporting information
p. 6975 - 6979
(2015/11/27)
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- Synthesis and biological evaluation of phenoxyacetic acid derivatives as novel free fatty acid receptor 1 agonists
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Free fatty acid receptor 1 (FFA1) is a new potential drug target for the treatment of type 2 diabetes because of its role in amplifying glucose-stimulated insulin secretion in pancreatic β-cell. In the present studies, we identified phenoxyacetic acid derivative (18b) as a potent FFA1 agonist (EC50 = 62.3 nM) based on the structure of phenylpropanoic acid derivative 4p. Moreover, compound 18b could significantly improve oral glucose tolerance in ICR mice and dose-dependently reduced glucose levels in type 2 diabetic C57BL/6 mice without observation of hypoglycemic side effect. Additionally, compound 18b exhibited acceptable PK profiles. In summary, compound 18b with ideal PK profiles exhibited good activity in vitro and in vivo, and might be a promising drug candidate for the treatment of diabetes mellitus.
- Wang, Xuekun,Zhao, Tianxiao,Yang, Baowei,Li, Zheng,Cui, Jian,Dai, Yuxuan,Qiu, Qianqian,Qiang, Hao,Huang, Wenlong,Qian, Hai
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p. 132 - 140
(2015/02/18)
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- Catalyst-free photoredox addition-cyclisations: Exploitation of natural synergy between aryl acetic acids and maleimide
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Suitably functionalised carboxylic acids undergo a previously unknown photoredox reaction when irradiated with UVA in the presence of maleimide. Maleimide was found to synergistically act as a radical generating photoxidant and as a radical acceptor, negating the need for an extrinsic photoredox catalyst. Modest to excellent yields of the product chromenopyrroledione, thiochromenopyrroledione and pyrroloquinolinedione derivatives were obtained in thirteen preparative photolyses. In situ NMR spectroscopy was used to study each reaction. Reactant decay and product build-up were monitored, enabling reaction profiles to be plotted. A plausible mechanism, whereby photo-excited maleimide acts as an oxidant to generate a radical ion pair, has been postulated and is supported by UV/Vis. spectroscopy and DFT computations. The radical-cation reactive intermediates were also characterised in solution by EPR spectroscopy. UVA photolyses of aryloxy-, arylthio- and arylamino-acetic acids with maleimide yield oxa-, thia- and aza-tricyclo pyrroledione derivatives in the absence of a photoredox catalyst (see scheme). An intriguing mechanism has been proposed and has been supported and supplemented by NMR monitoring experiments, DFT computations and UV/Vis and EPR spectroscopy.
- Manley, David W.,Mills, Andrew,O'Rourke, Christopher,Slawin, Alexandra M. Z.,Walton, John C.
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supporting information
p. 5492 - 5500
(2014/05/20)
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- Nanosized ferric hydroxide catalyzed c-o cross-coupling of phenol and halides to generate phenoxy ether
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The iron-based catalyst can effectively catalyze the phenolic hydroxyl C-O bond formation reaction to give the corresponding phenoxy ethers. The reaction of phenol and methyl chloroacetate, for example, gives phenoxy acetic acid methyl ester in 98 % yield under the optimal reaction conditions. Among the iron-based catalysts, nanosized ferric hydroxide prepared through sol-gel method gives the best catalytic activity.
- Sun, Hongbin,Sun, Yuanhua,Tian, Xiaohua,Zhao, Yunxia,Qi, Xuan
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p. 6189 - 6191
(2013/07/26)
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- Synthesis of (±) travoprost and its analogs
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A new synthetic approach for the antiglaucoma agent, travoprost (1) has been developed in four steps from key intermediate (2). Key transformations include Horner-Wadsworth-Emmons reaction and separation of diastereomers to obtain (±) travoprost (1) and its analogs.
- Mudduluru, Harikrishna,Hindupur, Rama M.,Dubey, Pramod K.,Madhavaram, Shankar,Tatini, Lakshmikumar,Subbaraju, Gottumukkala V.
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experimental part
p. 234 - 241
(2012/04/18)
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- Antibacterial and antitubercular activities of some diphenyl hydrazones and semicarbazones
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Condensation of phenoxy or 4-bromophenoxy acetic acid hydrazide and substituted aryl semicarbazides with appropriate carbonyl compounds yield corresponding hydrazones and semicarbazones, respectively. The chemical structure of the synthesized compounds has been confirmed by UV, IR and 'H NMR spectral data. All the compounds have been investigated for their antibacterial activity against ten pathogenic strains and antitubercular activity against Mycobacterium tuberculosis H37 Rv. Compound 4f, Acetic acid, phenoxy-,[l-(4-chlorophenyl) ethylidene] hydrazide has been found to exhibit 80% inhibition in the preliminary antitubercular screening (MIC >6.25 |ig/mL).
- Raja,Agarwal,Mahajan,Pandeya,Ananthan
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scheme or table
p. 1384 - 1388
(2011/01/13)
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- Aza-Michael addition of acrylonitrile with 2-aryloxymethylbenzimidazole derivatives under microwave irradiation
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A simple, rapid, and highly efficient method has been developed for the aza-Michael addition of acrylonitrile to 2-aryl-oxymethylbenzimidazole derivatives in the presence of anhydrous potassium carbonate under microwave irradiation. A series novel of 1-cyanoethyl-2-aryloxymethylbenzimidazole derivatives have been prepared and characterised by 1H NMR, 13C NMR, IR spectra and elemental analysis.
- Wei, Tai-Bao,Hua, Mao-Tang,Shi, Hai-Xiong,Liu, Yong,Zhang, You-Ming
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scheme or table
p. 452 - 454
(2010/12/24)
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- Microwave-assisted esterification of diverse carboxylic acids and chiral amino acids
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A facile and efficient synthetic method of esters from their corresponding carboxylic acids and amino acids is described. The esterification reaction of carboxylic acids and amino acids could be greatly accelerated under microwave irradiation because the reactions described in this article took place in only 5 min with almost quantitative yields, and distinct acidity of catalytic acids was well tolerated. Unlike the racemation problem in microwave-assisted N-acylation reactions, the esters of chiral amino acids could be achieved with retention of configuration under this condition. Copyright Taylor & Francis Group, LLC.
- Yang, Qian,Wang, Xiao-Jian,Li, Zhi-Yu,Sun, Li,You, Qi-Dong
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experimental part
p. 4107 - 4115
(2009/04/04)
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- A rapid and high-yield synthesis of aryloxyacetic acid in one pot under microwave irradiation and phase transfer catalysis conditions
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A series of aryloxyacetic acid 3a-h has been synthesized in one pot under microwave irradiation and phase transfer catalysis conditions. By the optimization of the reaction condition, a rapid, high-yield and efficient method for the preparation of aryloxyacetic acid is reported.
- Wei, Tai-Bao,Liu, Hong,Li, Man-Lin,Zhang, You-Ming
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p. 1312 - 1314
(2007/10/03)
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- Rapid and high-yield synthesis of aryloxyacetates under microwave irradiation and phase-transfer catalysis conditions
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A series of methyl aryloxyacetates (3a-3f) have been synthesized by the reaction of substituted phenol with methyl chloroacetate under the conditions of microwave irradiation and phase-transfer catalysis. By the optimization of the reaction conditions, we developed a good method for the preparation of methyl aryloxyacetates, which have the advantages of high yields, short reaction times, ease of workup, and simple operation. Copyright Taylor & Francis, Inc.
- Wei, Tai-Bao,Liu, Hong,Li, Man-Lin,Zhang, You-Ming
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p. 1759 - 1764
(2007/10/03)
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- A rapid and high-yield synthesis of aryloxyacetyl hydrazides under microwave irradiation and with phase transfer catalysis
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A series of aryloxyacetyl hydrazides 4a-l were synthesised under microwave irradiation and phase transfer catalysis conditions. By the optimisation of the reaction conditions, a rapid, high-yield and efficient method for the preparation of aryloxyacety hydrazide was given.
- Wei, Tai-Bao,Liu, Hong,Li, Man-Lin,Zhang, You-Ming
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p. 432 - 433
(2007/10/03)
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- Synthesis of Aryloxyacetic Acids, Esters, and Hydrazides Assisted by Microwave Irradiation
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Under microwave irradiation on clay a series of transformations of a number of phenols into their aryloxyacetic acids 3 and then their methyl esters 4 and hydrazides 5 has been achieved efficiently in good yields.
- Hamid, Hamida M. Abdel,Ramadan, El Sayed,Hagar, Mohamed,El Ashry, El Sayed H.
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p. 377 - 382
(2007/10/03)
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- An efficient synthesis of aryloxyacetic acid and arylthioacetic acid esters
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The esterification of the aryloxyacetic acid and arylthioacetic acid catalysed by silica sulfuric acid results aryloxyacetic acid and arylthioacetic acid ester in 83-94% yields respectively under mild reaction conditions.
- Li, Ji-Tai,Li, Hong-Ya,Li, Hui-Zhang
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p. 416 - 417
(2007/10/03)
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- Relative reactivity of methyl iodide to ethyl iodide in nucleophilic substitution reactions in acetonitrile and partial desolvation accompanying activation
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Through the examination of empirical correlations involving activation parameters for nucleophilic substitution of methyl iodide and of ethyl iodide, nucleophiles have been classified into three series: (1) nucleophiles with two equivalent reaction sites, (2) nucleophiles with a chlorine atom in the para-position, and (3) nucleophiles with a single reaction site. Three types of partial desolvation processes accompanying activation have been deduced on the basis of these classifications. A major factor determining the relative reactivity of methyl iodide to ethyl iodide in the substitution reaction of an anionic nucleophile having a single reaction site in acetonitrile (kMeI/kEtI) is suggested to be partial desolvation around the nucleophilic center on going from reactant to transition-state.
- Kondo, Yasuhiko,Urade, Miyuki,Yamanishi, Yukari,Chen, Xinyu
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p. 1449 - 1454
(2007/10/03)
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- 4-Quinolylmethyl and 1-naphthylmethyl as benzyl-type protecting groups of carboxylic acids removable by homogeneous palladium-catalyzed hydrogenolysis
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4-Quinolylmethyl (4-QUI) esters are reduced by palladium-catalyzed hydrogenolysis by formate anion. The reaction conditions are compatible with reducible substituents or functional groups as aromatic bromo, alkene, aldehyde, ketone, nitrile, ethyl and benzyl esters. An allyl ester is cleaved selectively in the presence of a 4-QUI ester. 1-Naphthylmethyl (1-NAP) esters of α-amino acids could be deprotected without any racemization by the same methodology. (C) 2000 Elsevier Science Ltd.
- Boutros, André,Legros, Jean-Yves,Fiaud, Jean-Claude
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p. 2239 - 2246
(2007/10/03)
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- Structure-activity relationship of small-sized HIV protease inhibitors containing allophenylnorstatine
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We designed and synthesized a new class of peptidomimetic human immunodeficiency virus (HIV) protease inhibitors containing a unique unnatural amino acid, allophenylnorstatine [Apns; (2S,3S)-3-amino-2-hydroxy- 4-phenylbutyric acid], with a hydroxymethylcarbonyl (HMC) isostere as the active moiety. A systematic evaluation of structure - activity relationships for HIV protease inhibition, anti-HIV activities, and pharmacokinetic profiles has led to the delineation of a set of structural characteristics that appear to afford an orally available HIV protease inhibitor. Optimum structures, exemplified by 21f (JE-2147), incorporated 3-hydroxy-2- methylbenzoyl groups as the P2 ligand, (R)-5,5-dimethyl-1,3-thiazolidine-4- carbonyl (Dmt) residue at the P1' site, and 2-methylbenzylcarboxamide group as the P2' ligand. The present study demonstrated that JE-2147 has potent antiviral activities in vitro and exhibits good oral bioavailability and plasma pharmacokinetic profiles in two species of laboratory animals.
- Mimoto, Tsutomu,Kato, Ryohei,Takaku, Haruo,Nojima, Satoshi,Terashima, Keisuke,Misawa, Satoru,Fukazawa, Tominaga,Ueno, Takamasa,Sato, Hideharu,Shintani, Makoto,Kiso, Yoshiaki,Hayashi, Hideya
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p. 1789 - 1802
(2007/10/03)
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- Unexpected formation of acylformamidines by reaction of primary carboxamides with MeONa in DMF in the presence of CHCl3
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Dichlorocarbene, which is generated by reaction of CHCl3 with MeONa, is likely to chlorinate DMF to produce tile Vilsmeier-Haack-Arnold salt that in the presence of excess MeONa, gives DMF dimethylacetal (2). This latter reacts with primary amides to yield the corresponding N,N-dimethyl-N'-acylformamidines. Solid state structure of N-[(dimethylamino)methylene]phenoxyacetamide (4) obtained by X-ray crystallography is also reported.
- Anelli, Pier Lucio,Brocchetta, Marino,Copez, Debora,Palano, Daniela,Visigalli, Massimo,Paoli, Paola
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p. 15827 - 15832
(2007/10/03)
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- Reaction enthalpy of nucleophilic substitution of ethyl iodide in acetonitrile and its mechanistic significance
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Enthalpies of reaction for nucleophilic substitution of ethyl iodide have systematically been determined in acetonitrile. Through the concurrent analysis of empirical correlations between the reaction enthalpies and the specific interaction enthalpies for relevant anions with those between the logarithmic rates and the specific interaction enthalpies, partial desolvation accompanying activation has been deduced to be the major contributor to activation thermodynamic parameters, while the propensity of the reacting central atom in the nucleophilic anion plays a crucial role in determining reaction thermodynamic parameters. Semi-empirical molecular orbital calculations have supported these ideas. The application of the Marcus equation to the analysis of reaction characteristics in these reactions is discussed.
- Kondo, Yasuhiko,Tsukamoto, Tamio,Kimura, Naoko
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p. 1765 - 1769
(2007/10/03)
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- Mild conversion of primary carboxamides into carboxylic esters
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Primary carboxamides are converted into the corresponding alkyl carboxylates by treatment with dimethylformamide dimethylacetal in the appropriate alcohol at 25-45°C. Yields are very good to excellent.
- Anelli, Pier Lucio,Brocchetta, Marino,Palano, Daniela,Visigalli, Massimo
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p. 2367 - 2368
(2007/10/03)
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- Synthesis of new 2-thiomethyl penem derivatives
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New penem thiolesters (4-5) were synthesized and 5 was hydrolyzed. 2-mercaptomethyl penem 7 is formed in situ and transformed into penem monothiocarbamates 9 and 10.
- Giannotti,Altamura
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p. 1567 - 1574
(2007/10/02)
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- SYNTHESIS OF N--ACETOHYDROXAMIC ACIDS, POTENTIAL INHIBITORS OF THE 5-LIPOXYGENASE
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The synthesis of the title compounds starts from methyl (3-subst.phenoxy)alkanoates II which are reduced to the corresponding aldehydes and then transformed to oximes V by reaction with hydroxylamine.Reduction with borane-pyridine complex gives the hydroxylamines VI which on diacetylation and partial deacetylation provide the hydroxamic acids VIII.
- Svoboda, Jiri,Palecek, Jaroslav
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p. 1317 - 1332
(2007/10/02)
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