- Synthesis and characterization of task-specific ionic liquids possessing two Broensted acid sites
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Task-specific ionic liquids possessing two Broensted acid sites with -COOH, HSO-4, or H2PO-4 groups have been designed, synthesized, and characterized. Under mild conditions and without any additional organic solvent, the esterification of isopropanol by chloroacetic acid could be carried out in these new task-specific ionic liquids. In comparison with most of acidic ionic liquids in current use, these ionic liquids are halogen free and more environmentally benign as media and catalysts. Copyright Taylor & Francis Group, LLC.
- Liu, Dan,Gui, Jianzhou,Zhu, Xiangqin,Song, Lijuan,Sun, Zhaolin
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- Discovery of novel triazolophthalazine derivatives as DNA intercalators and topoisomerase II inhibitors
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A new series of triazolophthalazine derivatives was designed and synthesized as topoisomerase II (Topo II) inhibitors and DNA intercalators. The synthesized derivatives were evaluated in vitro for their cytotoxic activities against three human cancer cell lines: HepG2, MCF-7, and HCT-116 cells. Compound IXb was the most potent counterpart with IC50 values of 5.39 ± 0.4, 3.81 ± 0.2, and 4.38 ± 0.3 μM, as it was about 1.47, 1.77, and 1.19 times more active than doxorubicin (IC50 = 7.94 ± 0.6, 6.75 ± 0.4, and 5.23 ± 0.3 μM) against HepG2, MCF-7, and HCT-116 cells, respectively. Additionally, the binding affinity of the synthesized compounds toward the DNA molecule was assessed using the DNA/methyl green assay. Compound?IXb showed an excellent DNA binding affinity with an IC50 value of 27.16 ± 1.2 μM, which was better than that of the reference drug doxorubicin (IC50 = 31.02 ± 1.80 μM). Moreover, compound IXb was the most potent member among the tested compounds when investigated for their Topo II inhibitory activity. Furthermore, compound IXb induced apoptosis in HepG2 cells and arrested the cell cycle at the G2/M phase. Additionally, compound IXb showed Topo II poisoning effects at 2.5 μM and Topo II catalytic inhibitory effects at 5 and 10 μM. Finally, molecular docking studies were carried out against the DNA–Topo II complex and DNA, to investigate the binding patterns of the designed compounds.
- Sakr, Helmy,Ayyad, Rezk R.,El-Helby, Ali A.,Khalifa, Mohamed M.,Mahdy, Hazem A.
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- New Diesters Derived from Piperine: In silico Study and Evaluation of Their Antimicrobial Potential
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Piperine, previously extracted from black pepper (Piper nigrum L.), was used as a precursor for the synthesis of twelve new diester derivatives. The final products were obtained through the bimolecular nucleophilic substitution reaction (SN2) of the alkyl 2-chloroacetates and the salt of piperic acid, obtained from the basic hydrolysis of piperine. The compounds were synthesized with yields of 55-84% and characterized by infrared spectroscopy and 1H and 13C nuclear magnetic resonance. The evaluation of the compounds’ potential as new drug candidates was done through an in silico study of ADME properties (absorption, distribution, metabolization and excretion) and evaluation of antimicrobial activity against bacterial strains (Staphylococcus aureus and Pseudomonas aeruginosa), yeasts (Candida albicans and Candida tropicalis) and filamentous fungi (Aspergillus fumigatus, Aspergillus flavus and Aspergillus niger). The in silico study showed that the compounds were good drug candidates and antimicrobial evaluation demonstrated that 9 of the 12 compounds exhibited a minimum inhibitory concentration (MIC) ranging 1024-256 μg mL?1
- Barbosa-Filho, José M.,Brand?o, Maria Cláudia R.,Lima, Edeltrudes O.,Lira, Bruno F.,Neto, Hermes D.,Souza, Helivaldo D. S.,Trindade, Emmely O.,de Athayde-Filho, Petr?nio F.
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p. 1668 - 1678
(2020/10/09)
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- Synthesis, in silico Study and Antimicrobial Evaluation of New Diesters Derived from Phthaloylglycine
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New diesters derived from phthaloylglycine (7a-7i) were synthesized and their structures characterized by infrared, 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. The compounds were evaluated in an in silico study, which demonstrated positive features indicating a possible drug candidate. The diesters showed antifungal activity ranging from moderate to strong against strains of Candida. Compounds 7a, 7b, 7c, 7e and 7i had a moderate minimum inhibitory concentration (MIC) of 1024 μg mL?1 against all fungal strains, while 7h showed a very good MIC of 256 μg mL?1 against Candida albicans, Candida parapsilosis and Candida krusei and 64 μg mL?1 against Candida tropicalis. However, only 7h and 7i were able to inhibit bacterial growth of strains of Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa and Escherichia coli with an MIC of 1024 μg mL?1
- Alves, Francinara S.,Barbosa-Filho, José M.,Cordeiro, Laísa V.,Huang, Min-Fu N.,Lima, Edeltrudes O.,Neto, Hermes Diniz,Souza, Helivaldo D. S.,Trindade, Emmely O.,de Athayde-Filho, Petr?nio F.,de Lima, Priscila S. V.,de Oliveira, Rafael F.,de Sousa, Abra?o P.
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p. 953 - 962
(2020/10/14)
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- A pure Radix Salviae Miltiorrhizae usually different propyl ester synthesis method (by machine translation)
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The invention relates to a pure Radix Salviae Miltiorrhizae usually different propyl ester synthesis method, the method comprising the protocatechuic aldehyde as a starting raw material, after phenmethyl protection phenol hydroxy, Darzens ring oxidation, and then through the arrowhead class catalyst/hydrogen or Raney nickel/hydrogen catalytic reduction, to obtain pure Radix Salviae Miltiorrhizae usually different propyl ester. The method of the invention the synthetic product purity can be up to 98%, a yield of 55%. And the synthesis method of the invention, and is simple, short route, the productive rate is high, and is suitable for large-scale industrial production. (by machine translation)
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Paragraph 0052; 0058-0059
(2018/04/02)
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- Magnetically recoverable AlFe/Te nanocomposite as a new catalyst for the facile esterification reaction under neat conditions
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In this work, a new Fe3O4/AlFe/Te nanocomposite was synthesized by a one-step sol–gel method. The Fe3O4 magnetic nanoparticles (MNPs) were prepared and then mixed with aluminum telluride (Al2Te3) in an alkali medium to produce the desired catalyst. After characterization of the Fe3O4/AlFe/Te nanocomposite by SEM, TEM, EDS, XRD, and ICP analyses, it was used in the esterification reaction. This heterogeneous catalyst showed high catalytic activity in the esterification of commercially available carboxylic acids with various alcohols to produce the desired esters at high conversions under neat conditions. The Fe3O4/AlFe/Te nanocomposites were separated from the reaction mixture via an external magnet and re-used 8 times without significant loss of catalytic activity.
- Alavi, Seyed Jamal,Sadeghian, Hamid,Seyedi, Seyed Mohammad,Eshghi, Hossein,Salimi, Alireza
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- A method for preparing 2, 4 - dichlorophenoxyacetic acid (by machine translation)
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The invention provides a 2, 4 - dichlorophenoxyacetic acid preparation method, comprises the following steps, first alcohol and a halogenated acetic acid after the reaction, to obtain halogenated acetate; the 2, 4 - dichlorophen after reaction with the alkali, to obtain 2, 4 - II [...]; then the above-mentioned step to obtain the halo acetate with 2, 4 - dichlorophen salt, to obtain 2, 4 - dichlorophenoxy ester; then obtained the above-mentioned step 2, 4 - dichlorophenoxy ester hydrolytic reaction, to obtain the 2, 4 - dichloro acid and alcohol; finally the above-mentioned step returns mellowly obtained is used in the aforesaid step, recycling; the alcohol is C atom number greater than or equal to 2 alcohol. The invention adjusts the process route, from the improved on the basis of, the reaction process is cleaning, of the small amount of waste water, hydrolysis few by-products, high purity of the product, the conversion and yield higher; and process raw materials can be recycled, is suitable for large-scale industrial production. (by machine translation)
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Paragraph 0082; 0083; 0087; 0088
(2018/09/08)
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- CYCLIC PHOSPHATE SUBSTITUTED NUCLEOSIDE DERIVATIVES AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES
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The present invention relates to Cyclic Phosphate Substituted Nucleoside Derivatives of Formula (I), and pharmaceutically acceptable salts thereof, wherein A, B, Q, V, R1, R2 and R3 are as defined herein. The present invention also relates to compositions comprising a Cyclic Phosphate Substituted Nucleoside Derivative, and methods of using the Cyclic Phosphate Substituted Nucleoside Derivatives for treating or preventing HCV infection in a patient.
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Page/Page column 54
(2018/04/11)
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- A simple criterion for gas chromatography/mass spectrometric analysis of thermally unstable compounds, and reassessment of the by-products of alkyl diazoacetate synthesis
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Rationale: A principal limitation of gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS) is the thermal instability of analytes. We propose that the injector and column temperatures should not exceed the atmospheric pressure boiling point, without decomposition, of the highest homologue of the series being analyzed, instead of the time-consuming procedure of obtaining chromatograms using different temperatures. Methods: A series of thermally unstable diazocarbonyl compounds, alkyl diazoacetates (predicted limit of stability approx. 140 °C, the boiling point of ethyl diazoacetate), was selected for GC/MS analysis using standard equipment. Different GC separation conditions were selected so that the retention temperatures of target compounds were both below and above 140°C. Results: Analyzing alkyl diazoacetates within their thermal stability range permitted reanalysis of their typical synthesis by-products. No dialkyl fumarate or maleate impurities, principal decomposition products which have often been reported previously, were found. Instead, alkyl esters of glycolic acid nitrate, O2NOCH 2CO2R, and 'pseudo-dimeric' products, ROCO[C 2H3NO]CO2R, were discovered for the first time. Conclusions: Avoiding the decomposition of thermally unstable organic compounds during GC and/or GC/MS analysis requires estimating their degradation temperature limits. This limit can be estimated as being equal to the atmospheric pressure boiling point of the highest homologue in the homologous series under consideration that does not decompose on boiling. Copyright
- Kornilova, Tatiana A.,Ukolov, Anton I.,Kostikov, Rafael R.,Zenkevich, Igor G.
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p. 461 - 466
(2013/03/14)
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- Preparation of esters of mono- or dicarboxylic non-aromatic and aromatic acids
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The present invention relates to a method for preparing a carboxylic acid ester, wherein a carboxylic acid and/or a salt thereof is reacted with an alcohol in the presence of hydrogen chloride (HCl) and water to form the carboxylic acid ester, wherein the reaction is carried out using a starting reaction system wherein the molar ratio of HCl to carboxylic acid is at least 0.075 : 1 and the molar ratio of water to carboxylic acid is at least 0.25 : 1.
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Page/Page column 5
(2012/06/30)
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- PYRROLE ANTIFUNGAL AGENTS
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The invention provides compounds of formula (I), and pharmaceutically and agriculturally acceptable salts thereof; wherein: R1, R2, R3, R4, R5, R6, A1, L1 and n are as defined herein. These compounds and their pharmaceutically acceptable salts are useful in prevention or treatment of a fungal disease. Compounds of formula (I), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.
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Page/Page column 108
(2009/12/05)
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- Catalytic esterifications of carboxylic acids and alcohols by sodium bisulfate monohydrate
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The efficient esterification of primary and secondary alcohols with aliphatic carboxylic acids in the presence of a catalytic amount of sodium bisulfate monohydrate to afford the corresponding esters in high yields.
- Li, Yi-Qun
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p. 3901 - 3903
(2007/10/03)
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- Chiral Formamidines. The Total Asymmetric Synthesis of (-)-8-Azaestrone and Related (-)-8-Aza-12-oxo-17-desoxoestrone
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Attachment of the chiral formamidine moiety to 6-methoxy-1,2,3,4-tetrahydroisoquinoline afforded the key chiral, nonracemic precursor 8, upon which the azasteroid skeleton was constructed.Asymmetric alkylation with α-halo esters or β-halo ethers gave 15 and 22, respectively, in high ee's.Cyclization, following enamine formation with cyclopentanedione or cyclopentanone, led to the chiral steroidal skeletons 6 and 5, respectively.The final stereocenters, leading to 8-azaestrone 4 with unnatural absolute configuration (antipodal), were accomplished by intramolecular alkylation of (+)-6b and subsequent reduction and ether cleavage.For the 12-oxosteroid 3, the methyl at C-13 was inserted by initial conjugate reduction of the enone 5 with a copper hydride reagent (Stryker method) requiring the presence of a silyl chloride affording 21.The addition of methyl iodide to C-13 occurred after transforming the triethylsilyl enol ether, 21, to its lithium enolate.Stereochemical assignments for both azasteroids 3 and 4 were confirmed by spectroscopic means including circular dichroism curves.
- Meyers, A. I.,Elworthy, Todd R.
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p. 4732 - 4740
(2007/10/02)
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- Specific esterase activity of subtilisin toward esters of α-haloacids
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Esters of α-haloacids are specific substrates for subtilisin which catalyses their hydrolysis in aqueous media. The same esters undergo transesterifications in organic solvents in the presence of subtilisin immobilized on an alumina-phosphate complex.
- Pugniere,Juan, C. San,Previero
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p. 4883 - 4886
(2007/10/02)
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- Inhibitors of Cyclic AMP Phosphodiesterase. 4. Synthesis and Evaluation of Potential Prodrugs of Lixazinone (N-Cyclohexyl-N-methyl-4quinazolin-7-yl)oxy>butyramide, RS-82856)
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The cyclic AMP phosphodiesterase (cAMP PDE) inhibitor and cardiotonic agent lixazinone (N-cyclohexyl-N-methyl-4-quinazolin-7-yl)oxy>butyramide, RS-82856, 1) and its acid and base addition salts were found to be insufficiently soluble in formulations suitable for intravenous administration.These results prompted an investigation into potential prodrugs with enhanced aqueous solubility designed to deliver 1 by three distinct mechanisms: (1) decarboxylation of α-carboxamides; (2) hydrolytic loss of a solubilizing N-1-(acyloxy)methyl or (N,N-dialkylamino)methyl moiety; or (3) intramolecular closure of a guanidino ester or amide.The target compounds were evaluated as delivery systems for 1 by three criteria: (1) chemical conversion rate to 1 under physiological conditions; (2) inhibition of type IV cAMP PDE at a fixed time point; and (3) in vivo inotropic activity in anesthetized dogs by both intravenous and oral administration.Release of 1 from 4a (series 1) was found to be too slow to be of value as prodrug of 1, since decarboxylation could be induced only by strong acid, conditions under which hydrolytic ring opening was found to severely compete.Conversely, 1 was released too readily on exposure of (N,N-dialkylamino)methyl derivatives such as 8d (series 2) to physiological conditions, although no large increase in aqueous solubility was realized.Finally, both the physicochemical and in vitro studies indicated that ring closure of the guanidinium esters and amides 17a-k (series 3) to 1 was quantitative and pH- and time-dependent, suggesting the possibility of delivery of the open, water-soluble prodrug form, followed by closure to 1 in plasma.Detailed examination of these agents in vivo, however, demonstrated that only those compounds that rapidly cyclized to 1, as measured by plasma levels of 1, exhibited inotropic activity, indicating that the open prodrug form was not efficiently absorbed upon oral administration.
- Venuti, Michael C.,Alvarez, Robert,Bruno, John J.,Strosberg, Arthur M.,Gu, Leo,et al.
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p. 2145 - 2152
(2007/10/02)
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- Reduction of Nitroarenes to Anilines in Basic Alcoholic Media
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Substituted nitrobenzenes are reduced by alkoxide ions in alcohols to the corresponding azoxy and aniline derivatives.The reaction leading to anilines has been investigated in detail.Two different processes have been identified, both initiated by the condensation between the nitrosoarene intermediate (the first product of the reduction reaction) and the product of oxidation of the solvent.The imino derivative thus formed (ArN=CH-COR) may either undergo hydrolysis (to aniline) or form, through a series of redox processes, compounds containing the ArNH-CO moiety.These are also hydrolysed to anilines in a slower reaction.
- Prato, Maurizio,Quintily, Ugo,Scorrano, Gianfranco
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p. 1419 - 1424
(2007/10/02)
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