- Synthesis of alaremycin
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Methyl 5-azido-4-oxohexanoate was synthesized from 5-hexenoic acid in six steps and converted to the title compound by NaReO4- and CF 3SO3H-catalyzed reaction in Ac2CVCCl4 followed by hydrolysis of the methyl ester moiety. Georg Thieme Verlag Stuttgart.
- Wang, Yong-Gang,Wachi, Masaaki,Kobayashi, Yuichi
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Read Online
- Use of deuterium labeling studies to determine the stereochemical outcome of palladium migrations during an asymmetric intermolecular Heck reaction
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(Chemical Equation Presented) A series of deuterium labeling experiments showed that Pd migrations during an intermolecular asymmetric Heck reaction between phenyl triflate and various deuterated 2,3-dihydrofurans (2b, 2c, 2d, 2e) occurs exclusively by either syn-1,2-dyotropic shifts or a syn-chain-walking mechanism; no evidence was observed to support anti-1,2-dyotropic shifts or anti-β-H Pd eliminations during the formation of 6 and 7.
- Wheatley, Bronwen M. M.,Keay, Brian A.
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Read Online
- Complex Formation of Calcium Ions and Monosubstituted Succinic Acid Derivatives in Aqueous Solutions
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Complex formation of calcium ions with succinic acid monoamide and methyl hydrogen succinate at 25°C and ionic strength I = 0.3 (KC1) was studied by pH-potentiometric titration. The stability constants of the complexes were determined.
- Mitrofanova
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Read Online
- Oxidation of cyclohexanone and/or cyclohexanol catalyzed by Dawson-type polyoxometalates using hydrogen peroxide
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The oxidation of cyclohexanone, cyclohexanol or cyclohexanone/cyclohexanol mixture using as catalyst, Dawson-type polyoxometalates (POMs) of formula, α- and β-K6P2W18O62, α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62 and hydrogen peroxide, carried out at 90 °C with a reaction time of 20 h, led to a high number of mono- and di-acids which were identified by GC-MS. Levulinic, 6-hydroxyhexanoic, adipic, glutaric and succinic acids, major products were evaluated by HPLC. Regardless of the substrate nature, all POMs exhibited high catalytic activity with 94–99% of conversion, whereas the formation of the different products is sensitively related to both the composition and symmetry of the POMs and the substrate nature. The main products are adipic acid in the presence of α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62, levulinic acid in the presence of α1-K7P2Mo5VW12O62 and β-K6P2W18O62 and 6-hydroxyhexanoic acid in the presence of α- and β-K6P2W18O62. Graphical abstract: High catalytic activity was observed with?α- and?β-K6P2W18O62, α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62 Dawson-type for the oxidation of cyclohexanone, cyclohexanol or cyclohexanone/cyclohexanol mixture, in the hydrogen peroxide presence, to several oxygenated products. Adipic, levulinic and 6-hydroxyhexanoic acids are the main products. The peroxo- species formed in situ could be the active sites.[Figure not available: see fulltext.]
- Dermeche, Leila,Idrissou, Yasmina,Mazari, Tassadit,Moudjahed, Mohammed,Rabia, Cherifa
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- New compounds for a good old class: Synthesis of two Β-lactam bearing cephalosporins and their evaluation with a multidisciplinary approach
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Antimicrobial resistance is spreading massively in the world and is becoming one of the main health threats of the 21st century. One of the possible strategies to overcome this problem is to modify the known classes of antibiotics in a rational way, with the aim of tuning their efficacy. In this paper, we present the synthesis and the evaluation of the biological activity of a series of two β-lactam bearing cephalosporin derivatives, in which an additional isolated azetidinone ring, bearing different substituents, is joined to the classical cephalosporanic nucleus by a chain of variable length. A computational approach has been also applied in order to predict the molecular interactions between some representative derivatives and selected penicillin-binding proteins, the natural targets of β-lactam antibiotics. All these derivatives are active against Gram-positive bacteria, with MIC100 comparable or even better than that of the reference antibiotic ceftriaxone, and show no or very low cytotoxic activity on different cell lines. Overall, these molecules appear to be able to exert their activity in particular against microorganisms belonging to some of the species more involved in the development of multidrug resistance.
- Vigliotta, Giovanni,Giordano, Deborah,Verdino, Anna,Caputo, Ivana,Martucciello, Stefania,Soriente, Annunziata,Marabotti, Anna,De Rosa, Margherita
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supporting information
(2020/01/22)
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- Inverse Electron-Demand Diels-Alder Bioconjugation Reactions Using 7-Oxanorbornenes as Dienophiles
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Oligonucleotides, peptides, and peptide nucleic acids incorporating 7-oxanorbornene as a dienophile were reacted with tetrazines linked to either a peptide, d-biotin, BODIPY, or N-acetyl-d-galactosamine. The inverse electron-demand Diels-Alder (IEDDA) cycloaddition, which was performed overnight at 37 °C, in all cases furnished the target conjugate in good yields. IEDDA reactions with 7-oxanorbornenes produce a lower number of stereoisomers than that of IEDDA cycloadditions with other dienophiles.
- Agramunt, Jordi,Ginesi, Rebecca,Grandas, Anna,Pedroso, Enrique
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p. 6593 - 6604
(2020/07/14)
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- Synthesis, characterization, lipophilicity and cytotoxic properties of novel bis(carboxylato)oxalatobis(1-propylamine)platinum(IV) complexes
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A series of novel bis(carboxylato)oxalatobis(1-propylamine)platinum(IV) complexes as well as an ethylamine analog were synthesized. The compounds are either symmetrical with both axial ligands consisting of monoesters of succinic acid, or unsymmetrical, with one axial ligand being acetate. The compounds were characterized in detail by elemental analysis, mass spectrometry and multinuclear (1H, 13C, 15N, 195Pt) NMR spectroscopy. The reduction behavior was followed by NMR spectroscopy, while lipophilicity was determined by analytical reversed-phase HPLC measurements. The capacity of inhibiting proliferation of the human cancer cell lines A549 (non-small cell lung cancer), CH1(PA-1) (ovarian teratocarcinoma) and SW480 (colon carcinoma) was evaluated by the MTT assay. In the most sensitive cell line CH1(PA-1), all compounds exhibited IC50 values in the lower μM range. In general, the IC50 values decreased with increasing lipophilicity within the two compound series. Nevertheless, replacing one of the succinic ester ligands with acetate has a rather marginal impact on antiproliferative activity and is hardly disadvantageous.
- Hizal, Selin,Hejl, Michaela,Jakupec, Michael A.,Galanski, Markus,Keppler, Bernhard K.
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- Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates
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Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.
- Mills, L. Reginald,Zhou, Cuihan,Fung, Emily,Rousseaux, Sophie A. L.
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supporting information
p. 8805 - 8809
(2019/11/03)
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- Synthesis method of 5-aminolevulinic acid hydrochloride
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The invention relates to a synthesis method of 5-aminolevulinic acid hydrochloride. The method includes the steps that succinic anhydride is used as the raw material and subjected to monoesterification with methanol to obtain monomethyl succinate; monomethyl succinate and N,N-carbonyldiimidazole are subjected to a nucleophilic substitution reaction to obtain methyl 4-(1-imidazole)-4-oxobutanoate;methyl 4-(1-imidazole)-4-oxobutanoate and nitromethane are subjected to a nucleophilic substitution reaction under the catalysis of an alkali compound to obtain methyl 5-nitro-4-oxopentanoate; methyl5-nitro-4-oxopentanoate and a metallic reducing agent are subjected to a reduction reaction, and through hydrolysis, 5-aminolevulinic acid hydrochloride is obtained. The process is simple, the raw material is easy to obtain, no special rectification and recrystallization devices are needed for treating intermediate products, no toxic and expensive raw materials are used, the use of heavy metal reducing agents is avoided to prevent environmental pollution, the synthesis cost is low, the purity of the synthetic product can reach 97% in recrystallization detection, and the total yield is high andreaches 70% or above.
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Paragraph 0023; 0027; 0031; 0035; 0038
(2019/02/10)
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- Highly Efficient Multigram Synthesis of Dibenzoazacyclooctyne (DBCO) without Chromatography
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The synthesis of 4-[11,12-didehydrodibenzo[b,f]azocin-5(6H)-yl]-4-oxobutanoic acid, also known as dibenzoazacyclooctyne (DBCO) or aza-dibenzocyclooctyne (ADIBO), was optimized for large-scale preparations of at least 10 g with an overall yield of 42%.
- McNelles, Stuart A.,Pantaleo, Julia L.,Adronov, Alex
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p. 2740 - 2745
(2019/11/21)
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- Cyclohexyl-Fused, Spirobiindane-Derived, Phosphine-Catalyzed Synthesis of Tricyclic ?3-Lactams and Kinetic Resolution of ?3-Substituted Allenoates
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A C2-symmetric chiral phosphine catalyst, NUSIOC-Phos, which can be easily derived from cyclohexyl-fused spirobiindane, was introduced. A highly enantioselective domino process involving pyrrolidine-2,3-diones and γ-substituted allenoates catalyzed by NUSIOC-Phos has been disclosed. Diastereospecific tricyclic γ-lactams containing five contiguous stereogenic centers were obtained in high yields and with nearly perfect enantioselectivities. A kinetic resolution process of racemic γ-substituted allenoates was developed for the generation of optically enriched chiral allenoates.
- Wu, Mingyue,Han, Zhaobin,Li, Kaizhi,Wu, Ji'En,Ding, Kuiling,Lu, Yixin
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supporting information
p. 16362 - 16373
(2019/10/16)
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- Method for overcoming drug resistance of EGFR mutation and cancerous stemness of human non-small cell lung carcinoma
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EGFR mutation (T790M) and cancerous stemness have shown drug resistances in human non-small-cell lung cancer (NSCLC), thus development of novel drugs in overcoming drug resistances in the NSCLC therapy is highly desired. SP101 is a novel gefitinib derivative, which can bind the ATP-binding pocket of EGFR to inhibit its EGFR kinase activity. SP101 can reduce the drug resistances of EGFR mutation (T790M) and cancerous stemness in NSCLC. SP101 induced cancer cell death and apoptosis in the gefitinib-resistant EGFR mutation (T790M) H1975 cells. SP101 inhibited phosphorylated EGFR and its downstream Survivin proteins but conversely induced Caspase 3 activation for apoptosis induction. Moreover, SP101 could decrease Oct4 protein level and reduce Survivin proteins but conversely elicited active Caspase 3 in the xenograft human H1975 lung tumors in nude mice.
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Page/Page column 5
(2018/06/08)
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- PROCESS FOR THE PREPARATION AND ISOLATION OF CARBOXYLIC ESTERS
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The disclosed methods for preparing and isolating carboxylic esters ensure a high product purity and minimize technical complexity. These methods are based on the reaction of a carboxylic acid with an alcohol in an aqueous medium. In some examples, the alcohol is used both for the esterification and for the precipitation of the salts, preferably ammonium salts, formed in the synthesis.
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Paragraph 0074-0081
(2016/11/14)
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- Intermediate for standard auspicious Luo river (1R, 2S) - 2 - (2,3-difluorophenyl) method for the preparation of cyclopropylamines (by machine translation)
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The invention discloses a method for preparing ticagrelor midbody (1R,2S)-2-(2,3-difluorophenyl) cyclopropylamine, belonging to the technical fields of organic synthesis route design and preparation of raw material medicines and midbodies. The method comprises the following steps: performing alcoholysis on succinic anhydride, thereby obtaining mono-methyl succinate, performing acylating chlorination reaction on mono-methyl succinate, thereby obtaining a compound methyl 4-chloro-4-oxobutyrate, performing Fridel-Crafts reaction on methyl 4-chloro-4-oxobutyrate and o-difluorobenzene, thereby obtaining a compound methyl 4-ketone-4-(3,4-difluorophenyl) butyrate (IV), and further performing asymmetric reduction reaction, cyclization reaction and Hoffman degradation on the compound IV, thereby obtaining the compound (1R,2S)-2-(2,3-difluorophenyl) cyclopropylamine. Initial raw materials used in the method are low in cost and easy to obtain, the reaction condition is gentle, the operation is safe, simple and convenient, the environment pollution is small, and the key ticagrelor midbody prepared by using the method is simple and convenient in after treatment, and is beneficial to on-scale production.
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Paragraph 0037; 0062; 0063
(2017/03/23)
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- A succinic acid mono methyl ester preparation method (by machine translation)
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The present invention provides a kind of succinic acid mono methyl ester preparation method, content is a succinic anhydride with methanol to enter into the static mixer of monoester reaction, reaction effluent entering the higee reactor, at the same time, water vapor is introduced to the high gravity reactor; after the reaction is separated by cooling the liquid phase material succinic acid mono methyl ester. The present invention succinic acid mono methyl ester of reasonable technological process of the preparation method, the separation method is simple, the purity of the product is high, good quality, high yield. (by machine translation)
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Paragraph 0022; 0023; 0042
(2017/02/09)
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- COMPOUND FOR PROMOTING APOPTOSIS OF CANCER CELLS AND A PHARMACEUTICAL COMPOSITION CONTAINING THE SAME AND USES THEREOF
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The present invention provides a compound of Formula (I) and a salt thereof, wherein, m is an integer of 2 to 7, and R is independently at least one selected from the group consisting of hydrogen and C1-C20 alkyl. The compound promotes apoptosis in cancer cell and inhibits its growth. The present invention also provides a pharmaceutical composition which comprises the compound of Formula (I), a salt thereof and a pharmaceutically acceptable carrier. The present invention further provides a method for production of the pharmaceutical composition used for treating cancer.
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Paragraph 0044-0046
(2016/04/20)
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- Compound for promoting apoptosis of cancer cells, pharmaceutical composition containing the same and uses thereof
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The present invention provides a compound of a formula (I) and a salt thereof, wherein m is an integer of 2 to 7, and R is independently at least one selected from the group consisting of hydrogen and C1-C20 alkyl. The compound promotes apoptosis in cancer cells and inhibits growth of the cancer cells. The present invention also provides a pharmaceutical composition which comprises the compound of the formula (I), a salt thereof and a pharmaceutically acceptable carrier. The present invention further provides uses of the compound of the formula (I) or the salt thereof in preparation of medicine for treating cancer.
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Paragraph 0050; 0052; 0053
(2016/10/09)
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- Synthesis and photophysical properties of a new BODIPY-based siloxane dye
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A fluorescent dye comprising four BODIPY derivatives conjugated to a cyclotetrasiloxane core was synthesized by consecutive hydrosilylation and esterification reactions. Photophysical properties of the dye in various organic solvents were investigated. It was shown that due to a fourfold extinction coefficient increase and a moderate quantum yield decrease the brightness of the tetra-BODIPY dye in low-polarity solvents, calculated per molecule, increased 3 times when compared to mono-BODIPY. By contrast, in polar solvents there was a dramatic drop in brightness apparently associated with intramolecular interactions of the low-polar BODIPY chromophores.
- Pakhomov, Alexey A.,Kononevich, Yuriy N.,Stukalova, Maria V.,Svidchenko, Evgeniya A.,Surin, Nikolay M.,Cherkaev, Georgy V.,Shchegolikhina, Olga I.,Martynov, Vladimir I.,Muzafarov, Aziz M.
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supporting information
p. 979 - 982
(2016/02/18)
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- Synthesis of α-Nitro Carbonyls via Nitrations in Flow
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Reported is a safe, rapid method for the synthesis of α-nitro esters via the trapping of nitronium ions. The two-stage nitration and subsequent deacetylation of readily available 1,3-dicarbonyl compounds was achieved using a biphasic semicontinuous approach. α-Nitro esters and amides were obtained in good overall yields (53-84%). Some of the α-nitro-1,3-dicarbonyl intermediates exhibit enhanced reactivity and undergo an acid-catalyzed Nef-type reaction to α-oxo-carbonyls.
- Chentsova, Anna,Ushakov, Dmitry B.,Seeberger, Peter H.,Gilmore, Kerry
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p. 9415 - 9421
(2016/10/17)
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- Selective monomethyl esterification of linear dicarboxylic acids with bifunctional alumina catalysts
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An environmentally friendly protocol for the selective protection of dicarboxylic acids is reported using methanol as a cheap esterifying agent and alumina as a heterogeneous catalyst; the selectivity of the process has been ascribed to a balanced acidity/basicity of the bifunctional alumina catalyst.
- Santacroce, Veronica,Bigi, Franca,Casnati, Alessandra,Maggi, Raimondo,Storaro, Loretta,Moretti, Elisa,Vaccaro, Luigi,Maestri, Giovanni
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supporting information
p. 5764 - 5768
(2016/11/06)
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- A PROCESS FOR PREPARING SUCCINATE ESTER
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This invention relates to a process for preparing succinate ester from a succinic acid salt present in a fermentation broth. In the first stage of this invention, renewable carbon resources are utilized to produce succinic acid in the form of a succinic acid salt through biological fermentation. The succinic acid salt present in the fermentation broth is subjected to double displacement reaction with a strong acid leading to the release of succinic acid. Succinic acid is recovered by fractional crystallization integrated with an alcohol washing step and subjected to esterification reaction to produce succinate ester which is purified by fractional distillation. The succinate ester thus obtained is converted into 1,4-butanediol, gamma-butyrolactone and tetrahydrofuran through hydrogenation reactions. The succinate ester can also be hydrolyzed to yield highly pure succinic acid.
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Paragraph 0098
(2016/11/07)
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- PROCESS FOR THE PREPARATION OF DIALKYL SUCCINATE FROM MALEIC ANHYDRIDE
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A process for the production of dialkyl succinate from a feedstock comprising maleic anhydride, said process comprising the steps of providing the feed in the liquid phase to a reactor operated at a temperature of at least about 150°C; contacting said feed with hydrogen at a pressure of at least about 300 psig in the presence of an acid tolerant catalyst and an alkanol wherein at least some of the carbon carbon double bonds of the maleic anhydride are hydrogenated to form succinic acid and that the heat generated promotes esterification to dialkyl succinate acid in situ; and recovering a stream comprising dialkyl succinate from the reactor.
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Page/Page column 11; 12
(2015/05/05)
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- Tetracarboxylatoplatinum(IV) complexes featuring monodentate leaving groups - A rational approach toward exploiting the platinum(IV) prodrug strategy
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A series of novel symmetrically and unsymmetrically coordinated platinum(IV) complexes with monodentate carboxylato ligands was synthesized. The compounds exhibit a general coordination sphere of [Pt(en)(OCOR)2(OCOR′)(OCOR″], where the carboxylato ligands are represented by acetato and succinic acid monoester ligands. Dicarboxylatoplatinum(II) complexes were synthesized and oxidized symmetrically or unsymmetrically to obtain platinum(IV) complexes, which were subsequently carboxylated with noncyclic anhydrides. The compounds were investigated in detail by elemental analysis, mass spectrometry, infrared and multinuclear (1H, 13C, 15N, 195Pt) NMR spectroscopy as well as by X-ray diffraction in some cases. The reduction behavior was followed by NMR spectroscopy, while stability and lipophilicity were examined by analytical reversed phase HPLC measurements. Cytotoxic properties were studied in three human cancer cell lines derived from cisplatin sensitive ovarian teratocarcinoma (CH1/PA-1), cisplatin insensitive colon carcinoma (SW480) and non-small cell lung cancer (A549). Thereby, the most lipophilic (yet water soluble) platinum(IV) complexes showed promising IC50 values in the low micromolar and even nanomolar range, demonstrating the significant advantage of using equatorially coordinated monodentate carboxylato ligands.
- H?fer, Doris,Varbanov, Hristo P.,Legin, Anton,Jakupec, Michael A.,Roller, Alexander,Galanski, Markus,Keppler, Bernhard K.
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p. 259 - 271
(2015/12/23)
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- Bis- and Tris(carboxylato)platinum(IV) Complexes with Mixed Am(m)ine Ligands in the trans Position Exhibiting Exceptionally High Cytotoxicity
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A series of seven diam(m)inebis(carboxylato)dihydroxidoplatinum(IV) and eleven diam(m)inetris(carboxylato)hydroxidoplatinum(IV) complexes with am(m)ine ligands in the trans position was synthesized and characterized by multinuclear 1H, 13C, 15N, 195Pt NMR spectroscopy. IC50 values for all eighteen substances were determined by means of the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay for three human cancer cell lines. In cisplatin-sensitive CH1(PA-1) cancer cells, diam(m)inebis(carboxylato)dihydroxidoplatinum(IV) complexes displayed 50 % inhibitory concentrations in the micromolar range, whereas for the most lipophilic compounds of the diam(m)inetris(carboxylato)hydroxidoplatinum(IV) series, promising IC50 values in the nanomolar range were found.
- Hoffmeister, Bj?rn R.,Hejl, Michaela,Jakupec, Michael A.,Galanski, Markus,Keppler, Bernhard K.
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p. 1700 - 1708
(2015/04/14)
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- Novel penicillin-type analogues bearing a variable substituted 2-azetidinone ring at position 6: Synthesis and biological evaluation
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The synthesis and the biological activity of novel semi-synthetic β-Lactam compounds containing an azetidinone moiety joined to the amino-nitrogen of the (+)-6-aminopenicillanic acid (6-APA) as new antibacterial agents is reported. The synthesized compounds were screened for their in vitro antimicrobial activity against a panel of Gram positive and Gram negative pathogens and environmental bacteria. Tested compounds displayed good antimicrobial activity against all tested Gram positive bacteria and for Staphylococcus aureus and Staphylococcus epidermidis antimicrobial activity resulted higher than that of the reference antibiotic. Additionally, in vitro cytotoxic screening was also carried out indicating that the compounds do not cause a cell vitality reduction effective at concentration next to and above those shown to be antimicrobial.
- De Rosa, Margherita,Vigliotta, Giovanni,Palma, Giuseppe,Saturnino, Carmela,Soriente, Annunziata
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p. 22044 - 22057
(2016/01/25)
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- PROCESS FOR THE PREPARATION OF SUCCINIC ACID ESTER
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A process for the production of dialkyl succinate from a bio-succinic acid feedstock comprising the steps of; (a) feeding solid bio-succinic acid to a first reactor where it is contacted with alkanol, said first reactor being operated at a suitable temperature and pressure to enable autocatalytic esterification to occur; (b) passing a stream removed from the first reactor comprising unreacted succinic acid, mono alkyl ester, dialkyl ester, alkanol, water and impurities to a point at or near the top of a reaction zone columm operated at temperatures and pressures to enable esterification of the succinic acid and further esterification of the mono alkyl ester, and passing said stream in counter-current reaction to upflowing additional alkanol; (c) removing a stream from at or near the bottom of the reaction zone column comprising components selected from residua! succinic acid, mono alkyl ester, dialkyl ester, impurities and alkanol and passing said stream to a bottoms stream separation zone where said di-alkyl ester is separated from alkanol, and from the succinic acid, mono alkyl ester and impurities; (d) recycling the succinic acid and mono alkyl ester to the reaction zone column; (e) removing at least some of the impurities as a purge; and (f) removing a stream comprising alkanol, water and organic components from at or near the top of the reaction zone column and passing said stream to a top stream distillation zone where the alkanol is separated, from the water and from the organic components and recycling the organic components to the reaction zone column.
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Page/Page column 18
(2015/06/18)
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- PROCESS FOR THE PREPARATION OF SUCCINIC ACID ESTER
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A process for the production of dialkyl succinate from a bio-succinic acid feedstock comprising the steps of: feeding bio-succinic acid to a point at or near the bottom of a reaction distillation zone column operated at temperatures and pressures to enable esterification of the succinic acid and passing said stream co-currently with upflowing alkanol such that said esterification reaction occurs: removing an overhead vapour stream from at or near the top of the reaction distillation zone column comprising di-ester, alkanol, water of esterification and organic components and passing said stream to an alkanol separation column where the alkanol is separated from the water of esterification and from the organic components; removing a side draw from the alkanol separation column from a point below the feed point thereto, said side draw comprising partially immiscible organic and aqueous phases; passing said side draw to phase separation apparatus where the partially immiscible organic and aqueous phases are separated; passing said organic phase to a column where the dialkyl succinate is separated from residual water and other organic components; and recovering the dialkyl succinate.
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Page/Page column 21-22; 24
(2015/06/18)
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- Optimization of gefitinib analogues with potent anticancer activity
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The interactions of gefitinib (Iressa) in EGFR are hydrogen bonding and van der Waals forces through quinazoline and aniline rings. However the morpholino group of gefitinib is poorly ordered due to its weak electron density. A series of novel piperazino analogues of gefitinib where morpholino group substituted with various piperazino groups were designed and synthesized. Most of them indicated significant anti-cancer activities against human cancer cell lines. In particular, compounds 52-54 showed excellent potency against cancer cells. Convergent synthetic approach has been developed for the synthesis of gefitinib intermediate which can lead to gefitinib as well as numerous analogues.
- Yin, Kai-Hao,Hsieh, Yi-Han,Sulake, Rohidas S.,Wang, Su-Pei,Chao, Jui-I.,Chen, Chinpiao
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supporting information
p. 5247 - 5250
(2015/01/08)
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- An expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters
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Phthalic, maleic and succinic anhydrides have been reacted with aromatic amines to obtain the corresponding monoacid monoamides. The latter have been each transformed into the corresponding cyclic imide derivatives by treating with SOCl2. Alternatively, anhydrides have been reacted with methanolic KOH to obtain monomethyl ester derivatives which on reaction with aromatic amines in the presence of EDC. HCl and HOBt give cyclic imide derivatives. Reaction of monoacid monoamides independently, with SOCl 2 at 0-5°C give the monoamide monoester derivatives. Treatment of monoamide monoester of malic anhydride with NaBH4 leads to the unusual reduction of C=C grouping as well as the carbonyl group of the ester group to from monoamide monoalcohol of succinic anhydride. Preparation of monoamide monoalcohol of succinic anhydride can also be achieved by chemoselective reduction of monoamide monoester of malic anhydride with Mg turnings yielding monoamide monoester of succinic anhydride followed by reduction of the latter with NaBH4.
- Kumar, Padam Praveen,Reddy, Y. Dathu,Kumari, Y. Bharathi,Devi, B. Rama,Dubey
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p. 392 - 398
(2014/05/06)
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- NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer. Part III: Studies on keto esters and acids
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The development of "molecular rulers" would allow one to quantitatively locate the penetration depth of intercalants within lipid bilayers. To this end, an attempt was made to correlate the 13C NMR chemical shift of polarizable "reporter" carbons (e.g., carbonyls) of intercalants within DMPC liposomal bilayers - with the polarity it experiences, and with its Angstrom distance from the interface. This requires families of molecules with two "reporter carbons" separated by a known distance, residing at various depths/polarities within the bilayer. For this purpose, two homologous series of dicarbonyl compounds, methyl n-oxooctadecanoates and the corresponding n-oxooctadecanoic acids (n = 4-16), were synthesized. To assist in assignment and detection several homologs in each system were prepared 13C-enriched in both carbonyls. Within each family, the number of carbons and functional groups remains the same, with the only difference being the location of the second ketone carbonyl along the fatty acid chain. Surprisingly, the head groups within each family are not anchored near the lipid-water interface, nor are they even all located at the same depth. Nevertheless, using an iterative best fit analysis of the data points enables one to obtain an exponential curve. The latter gives substantial insight into the correlation between polarity (measured in terms of the Reichardt polarity parameter, ET(30)) and penetration depth into the liposomal bilayer. Still missing from this curve are data points in the moderate polarity range.
- Afri, Michal,Alexenberg, Carmit,Aped, Pinchas,Bodner, Efrat,Cohen, Sarit,Ejgenburg, Michal,Eliyahu, Shlomi,Gilinsky-Sharon, Pessia,Harel, Yifat,Naqqash, Miriam E.,Porat, Hani,Ranz, Ayala,Frimer, Aryeh A.
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p. 105 - 118
(2015/02/19)
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- Diorganotin complexes of carboxylates: Synthesis and characterization
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Diorganotin complexes of monoisopropyl and monomethyl nadiate, succinate, and phthalate were synthesized and characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, and 119Sn NMR spectroscopic techniques. The spectroscopic investigation demonstrated that carboxylate is bidentate in the diorganotin complexes. On the basis of 1J(119Sn-13C) and 2J(119Sn-1H) values, C-Sn-C bond angles were also calculated. The newly synthesized complexes were also screened for their antibacterial activities against Gram-positive and Gram-negative pathogenic strains of bacteria.
- Chilwal, Asha,Deep, Gagan,Malhotra, Priti,Narula
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p. 1046 - 1057
(2013/07/28)
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- Insights into soluble guanylyl cyclase activation derived from improved heme-mimetics
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Recently, the structure of BAY 58-2667 bound to the Nostoc sp. H-NOX domain was published. On the basis of this structural information, we designed BAY 58-2667 derivatives and tested their effects on soluble guanylyl cyclase (sGC) activity. Derivative 20 activated sGC 4.8-fold more than BAY 58-2667. Co-crystallization of 20 with the Ns H-NOX domain revealed that the increased conformational distortion at the C-terminal region of αF helix containing 110-114 residues contributes to the higher activation triggered by 20.
- Von Wantoch Rekowski, Margarete,Kumar, Vijay,Zhou, Zongmin,Moschner, Johann,Marazioti, Antonia,Bantzi, Marina,Spyroulias, Georgios A.,Van Den Akker, Focco,Giannis, Athanassios,Papapetropoulos, Andreas
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supporting information
p. 8948 - 8952
(2013/12/04)
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- The development of first Staphylococcus aureus SplB protease inhibitors: Phosphonic analogues of glutamine
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Produced by Staphylococcus aureus, SplB belongs to the chymotrypsin-like serine protease family. Since the biological role of SplB protease is unknown, the design and application of its specific inhibitors may help to reveal the function of this enzyme. Until now no SplB inhibitors have been reported. Herein, we present the design and synthesis of novel α-aminophosphonic analogues of glutamine, as well as their peptidyl derivatives. The inhibitory effects of these compounds towards the newly discovered SplB serine protease from S. aureus are characterized. We have also investigated the influence of aromatic ester substituents on inhibitory potency towards SplB. One of the compounds - Cbz-Glu-Leu-GlnP(OC6H4-4-O-CH 3)2 - displayed an apparent second-order inhibition rate value of 1400 M-1 s-1.
- Ewa, Burchacka,MacIej, Walczak,Marcin, Sienczyk,Grzegorz, Dubin,Michal, Zdzalik,Jan, Potempa,Jozef, Oleksyszyn
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supporting information; experimental part
p. 5574 - 5578
(2012/09/22)
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- Synthesis and photovoltaic properties of a new thiophene-cyclopentadiene- based conjugated polymer
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A new low-band gap polymer containing thiophene and cyclopentadiene, poly(5,2,2'-dioctyldithiophenylcyclopentadiene) (PDTCP), has been synthesized via the FeCl3 oxidative polymerization. PDTCP showed a broad absorption band and a low energy band gap of 1.82 eV. The photoluminescence (PL) of PDTCP is completely quenched upon addition of PCBM indicative of efficient charge transfer. Bulk heterojunction organic photovoltaic cells (OPVs) fabricated from PDTCP as an electron donor showed an open-circuit voltage (VOC) of 0.50 V, a short-circuit current (JSC) of 1.24 mA/cm2, and the power conversion efficiency of up to 0.20% under AM 1.5 (100 mW/cm2). Copyright
- Lim, Eunhee,Lee, Sungkoo,Lee, Kyeong K.
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scheme or table
p. 4194 - 4198
(2012/09/22)
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- HYDROGENATION AND ESTERIFICATION TO FORM DIESTERS
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A process is disclosed which employs hydrogenation and esterification to form alkyl diesters. The process subjects an unrefined or otherwise not purified composition comprising maleic anhydride production residue to the processes of hydrogenation and esterification and forming diesters at high conversion efficiency.
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Page/Page column 16-17
(2011/02/24)
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- COMPOUNDS AND METHODS
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Disclosed are compounds having the formula: wherein X1, X2, X3, R1, R2, R3, R4, Y, A, n and L are as defined herein, and methods of making and using the same.
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Page/Page column 65-66
(2011/08/04)
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- ESTERAMIDE SOLVENTS/COALESCING AGENTS IN PHYTOSANITARY, CLEANING, DEGREASING, STRIPPING, LUBRICATING, COATING, AND PIGMENT/INK COMPOSITIONS
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Esteramide compounds are useful solvents/coalescing agents for a variety of phytosanitary, cleaning, degreasing, stripping, lubricating, coating and pigment/ink compositions.
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Page/Page column 17
(2011/07/29)
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- NEAR-INFRARED ABSORBING FILM COMPOSITIONS
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A curable liquid formulation containing at least (i) one or more near-infrared absorbing triphenylamine -based dyes, and (ii) one or more casting solvents. The invention is also directed to solid near- infrared absorbing films composed of crosslinked forms of the curable liquid formulation. The invention is also directed to a microelectronic substrate containing a coating of the solid near-infrared absorbing film as well as a method for patterning a photoresist layer coated on a microelectronic substrate in the case where the near-infrared absorbing film is between the microelectronic substrate and a photoresist film.
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Page/Page column 29
(2011/04/13)
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- METHOD FOR PRODUCING OLEFINS
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The present invention provides a method to produce olefins by the decarboxylation of organic carboxylic acids in the presence of an organopalladium catalyst.
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Page/Page column 14-15
(2011/10/31)
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- KMnO4-mediated oxidation as a continuous flow process
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An efficient and easily scalable transformation of alcohols and aldehydes to carboxylic acids and nitroalkane derivatives to the corresponding carbonyls and carboxylic acids using permanganate as the oxidant within a continuous flow reactor is reported. Notably, the generation and downstream processing of MnO2 slurries was not found to cause any blocking of the reactor when ultrasound pulses were applied to the flow system.
- Sedelmeier, Joerg,Ley, Steven V.,Baxendale, Ian R.,Baumann, Marcus
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supporting information; experimental part
p. 3618 - 3621
(2010/11/17)
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- Antiproliferative compounds and therapeutic uses thereof
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Inhibitors of the oncogenic tyrosine kinase ALK and of the Bcr-Abl mutant T315I Bcr-Abl, such as a compound of formula (I): wherein Q, T, W, K, J, Y, X, Z are independently selected from C, N, S, O, provided that the corresponding rings are (hetero)aromatic; n = 0 or 1; q = 1 or 2; pharmaceutical compositions containing the same and their use for the treatment of hyper-proliferative diseases.
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Page/Page column 24
(2009/10/18)
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- Phosphine-mediated olefination between aldehydes and allenes: An efficient synthesis of trisubstituted 1,3-dienes with high E-selectivity
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The phosphine-mediated olefination of aldehydes with electron-deficient allenes to afford trisubstituted conjugated dienes in fair to excellent yields with high E-selectivity is described. The reaction represents a new reactivity pattern of allenes with aldehydes and also provides a highly stereoselective synthetic method for preparing conjugated dienes. In the reaction, the phosphine acts as a nucleophilic promoter to generate in situ an active phosphorus ylide which mediates the intermolecular olefination.
- Xu, Silong,Zhou, Lili,Zeng, San,Ma, Renqin,Wang, Zhihong,He, Zhengjie
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supporting information; scheme or table
p. 3498 - 3501
(2009/12/01)
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- A new method for constructing quaternary carbon centres: Tandem rhodium-catalysed 1,4-addition/intramolecular cyclisation
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The efficient tandem rhodium-catalysed 1,4-addition/cyclisation of 1,1′-alkenes using arylzinc chlorides is described. The simple one-step synthesis of substituted cyclopentanone and cyclohexanone derivatives is performed from acyclic precursors using relatively low catalyst loadings under mild conditions. A new quaternary carbon centre is created during the cyclisation step.
- Le Notre, Jerome,Van Mele, David,Frost, Christopher G.
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p. 432 - 440
(2008/02/07)
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- On the synthesis of cepacin A
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Efforts directed toward a total synthesis of cepacin A is presented in full detail. The C-7, C-8, and C-9 stereogenic centers in the target molecule were derived from d-arabinose. The configuration of the allene axis was controlled at the bromoallenation step by the C-10 configuration of the precursor. An unexpected yet very interesting phenomenon was observed with the bromoallenation, where the α-isomer of the propargylic alcohol 31 was entirely resistant to the conditions that worked so well for its β-counterpart. The problem was eventually solved by careful tuning of the size of the neighboring groups based on the clue obtained from conformational analysis. The diyne moiety was incorporated into the molecular framework through a coupling of the TMS protected diyne with a proper bromoallene under the Sonogashira conditions with EtOAc as the solvent. Use of other solvents at this step led to complete failure.
- Tang, Chao-Jun,Wu, Yikang
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p. 4887 - 4906
(2008/02/01)
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- Novel (3,5-di-tert-butyl-2-hydroxy-phenylcarbamoyl)-alkanoic acids as potent antioxidants
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A series of novel phenolic antioxidants of amphiphilic structure has been synthesized. Investigations into the influence of aliphatic spacer length and nature of a hydrophilic anchor on the antioxidant activity allowed elucidating certain structure requirements for the membrane-addressed antioxidant designing.
- Lodyato, Vladimir I.,Yurkova, Irina L.,Sorokin, Viktor L.,Shadyro, Oleg I.,Dolgopalets, Vladimir I.,Kisel, Mikhail A.
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p. 4253 - 4256
(2007/10/03)
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- Kinetics of citraconic anhydride formation via condensation of formaldehyde and succinates
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Formation of citraconic anhydride via condensation of succinic acid and its derivatives with formaldehyde is carried out over γ-alumina catalyst in a continuous fixed-bed reactor. Dimethyl succinate and Formalin (37 wt % formaldehyde, 10 wt % methanol in water) are the preferred feed materials for the reaction; catalyst activity is sustained with Formalin relative to that with other formaldehyde sources such as trioxane or Formcel, because the water in Formalin inhibits coke formation. With this feed combination, a total citraconate yield of 31% of theoretical with 72% selectivity is achieved at a weight hour space velocity of 0.9 kg of succinate/kg of catalyst/h, a succinate to formaldehyde molar feed ratio of 1:2, and a temperature of 380 °C. The reaction is free from mass transfer limitations at these conditions. A kinetic model is presented that describes product distributions and reactant conversion as a function of space velocity and temperature. The reaction system is part of an overall process to produce itaconic acid from renewable resource-based succinic acid.
- Shekhawat, Dushyant,Nagarajan, Kirthivasan,Jackson, James E.,Miller, Dennis J.
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p. 611 - 617
(2013/09/06)
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- Montmorillonite clay: A novel reagent for the chemoselective hydrolysis of t-butyl esters
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A mild and highly selective hydrolysis of t-butyl esters has been achieved in high yields using montmorillonite KSF in refluxing acetonitrile. The method is compatible with a variety of protecting and functional groups such as BOC, Cbz, propargyl, allyl, benzyl, t-butyl ethers, allyl, methyl and benzyl esters present in the molecule.
- Yadav,Reddy, B. V. Subba,Rao, K. Sanjeeva,Harikishan
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p. 826 - 828
(2007/10/03)
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- Novel bifunctional chelating compounds containing hydroxamic acid residues
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New types of hydroxamic acid-based bifunctional chelators are provided. These chelators are designed to chelate metal ions that can be detected either by their paramagnetic or radioactive properties. Conjugation with peptides or protein can be achieved by the presence of a linker moiety in the molecular structure of these chelators.
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- Synthesis of optically active hydroxyesters using biocatalysts
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Optically active hydroxyesters were prepared using the fungus Aspergillus niger and the yeast Sacharomyces cerevisiae. Substrate is converted highly specifically into optically active isomers with 95% purity. The R-hydroxyester was isolated by asymmetric reduction. (R,R)-Tartaric acid of 60% optical purity was used as an inductor.
- Shakirzyanova,Abdukakharov,Abduvakhabov
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p. 279 - 281
(2007/10/03)
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- A combination of Friedel-Crafts and Lawesson reactions to 5-substituted 2,2′-bithiophenes
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γ-Keto esters (2) derivatives of thiophene were obtained from hemisuccinic esters and transformed to the corresponding amides (4). Lawesson's treatment of 2 and 4 gave the corresponding bithiophenes (5) with alkoxy or amino substituents.
- Raposo, M. Manuela M.,Kirsch
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p. 1487 - 1498
(2007/10/03)
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