- Comparison of reactivity in the cross metathesis of allyl acetate-derivatives with oleochemical compounds
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The metathesis of unsaturated oleochemicals is an excellent tool for generating α,ω-difunctional substrates, which are useful intermediates for polymer synthesis. This article describes the cross metathesis of allyl acetate and cis-1,4-diacetoxy-2-butene with methyl 10-undecenoate and methyl oleate, which are oleochemical key substrates. Detailed optimizations led to high conversion rates and yields of the desired products under mild reaction conditions by using a low concentration of commercially available homogeneous ruthenium catalysts.
- Behr, Arno,Toepell, Stephanie
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- Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids
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The synthesis of five novel methyl 10-undecenoate-based lipoconjugates of phenolic acids from undecenoic acid was carried out. Undecenoic acid was methylated to methyl 10-undecenoate which was subjected to a thiol-ene reaction with cysteamine hydrochloride. Further amidation of the amine was carried out with different phenolic acids such as caffeic, ferulic, sinapic, coumaric and cinnamic acid. All synthesized compounds were fully characterized and their structures were confirmed by spectral data. The antioxidant activity of the synthesized lipoconjugates of phenolic acids was studied by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay and also by the inhibition of linoleic acid oxidation in micellar medium by differential scanning calorimetry (DSC). The prepared compounds were also screened for their cytotoxic activity against five cell lines. It was observed that the lipoconjugates of caffeic acid, sinapic acid, ferulic acid, and coumaric acid displayed anticancer and anti-oxidant properties. The anticancer properties of these derivatives have been assessed by their IC50 inhibitory values in the proliferation of MDA-MB231, SKOV3, MCF7, DU 145 and HepG2 cancer cell lines.
- Narra, Naganna,Kaki, Shiva Shanker,Prasad, Rachapudi Badari Narayana,Misra, Sunil,Dhevendar, Koude,Kontham, Venkateshwarlu,Korlipara, Padmaja V.
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- Synthesis and biological evaluation of 3,6-dialkylsubstituted-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazoles
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Abstract: A series of 3,6-dialkyl-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazole (10) analogues were prepared through multistep synthesis and evaluated them for their antimicrobial and cytotoxic activities. Synthesis of target compounds was carried out using undecenoic acid as starting material, which is the renewable product of castor oil. The key step in the synthesis was formation of triazolo [3,4-b][1,3,4]thiadiazole using various free fatty acids in presence of POCl 3. It was observed that the undecenyl based triazolothiadiazole with butyl (6a), hexyl (6b) and lauryl (6f) derivatives exhibited promising antimicrobial activity against the tested strains. Particularly, Compound 6a exhibited the most promising activity with MIC value 3.9 μ g / mL against most of the tested strains. It also showed potent minimum bactericidal concentration activity with MIC value 7.8 μ g / mL against the tested strains. Cytotoxicity data revealed that most of the tested compounds revealed cytotoxic activity, Compounds 6b, 6d, 6f, 6g, 6h and 6i against SKOV3, 6d, 6e, 6f, 6g, 6h, 6i and 6j against MCF-7 and 6c, 6d, 6e,6g, 6h, 6i and6j against B16–F10 cell lines exhibited significant activities with IC 50 values ranged between 13.67 and 18.62 μ M. Interestingly, all the compounds were non toxic against Chinese hamster ovary cell (CHO-K1) normal cell. Graphical Abstract : A series of 3, 6-dialkyl triazolothiadiazole analogues were prepared using undecenoic acid, which is the renewable product of castor oil and evaluated them for their antimicrobial and cytotoxic activities. Few compounds showed good antimicrobial and cytotoxic activities. [Figure not available: see fulltext.].
- Venepally, Vijayendar,Sirisha,Kumar, C Ganesh,Krishna, E Vamshi,Misra, Sunil,Jala, Ram Chandra Reddy
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- Anchoring molecular magnets on the Si(100) surface
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Hydrosilylation by H-terminated silicon of the double bond of methyl 10-undecenoate with formation of a robust Si-C bond is the first step in a three-step procedure (see scheme) for anchoring the single-molecule magnet (SMM) [Mn12O12(OAc)16(H2O)4] (1) on the Si(100) surface.
- Condorelli, Guglielmo G.,Motta, Alessandro,Fragala, Ignazio L.,Giannazzo, Filippo,Raineri, Vito,Caneschi, Andrea,Gatteschi, Dante
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- Chemoenzymatic synthesis of macrocyclic polyamines
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(±)-Azamacrolides were synthesized via lipase-catalyzed intramolecular cyclization of (±)-hydroxy-azaesters. Further, the size of the macrocyclic lactones formed could be altered by the substituent on the nitrogen atom. This allows one to prepare a combinatorial library of azamacrolides from a small number of hydroxy-azaesters using this biocatalytic approach.
- Lu, Wei,Sih, Charles J.
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- Designing, synthesis, and antimicrobial action of oxazoline and thiazoline derivatives of fatty acid esters
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In this study, a novel series of oxazoline and thiazoline were designed as inhibitors of cytochrome P450 14 alpha-sterol demethylase (CYP51) from Candida albicans and peptide deformylase (PDF) of Escherichia coli. The long chain dibromo derivative of fatty acid esters on reaction with urea and thiourea gave their corresponding oxazolines and thiazolines, respectively. All the compounds were characterized by their spectral data (IR, 1H NMR, 13C NMR and MS) and tested for antibacterial and antifungal activity by disk diffusion assay and minimum inhibitory concentration by the broth microdilution method against gram-positive and gram-negative strains of bacteria as well as fungus strains. The investigation into antimicrobial screening revealed that all the compounds were found to be potent antimicrobial agents. After calculating likeness drug properties of the compounds by Prediction of Activity Spectra for Substances software, ADMET-related descriptors were computed to predict the pharmacokinetic properties for the active and bioavailable compounds by discovery studio 2.5. Molecular docking studies have been performed on PDF of E. coli and CYP 450-14DM of C. albicans to understand the mode of binding of the molecules in the active site of the receptor. Compounds (2-amino-5-(carbomethoxyoctyl)-1,3-oxazoline, 2-amino-5-(carbomethoxyoctyl)-1,3-thiazoline and 2-amino-4-pentyl-5-[(8’R)-8’ hydroxy (carbomethoxydecyl)-1,3-oxazoline) showed excellent antimicrobial activity nearly equivalent to the control compounds and compounds, 2-amino-4-octyl-5-(carbomethoxyheptyl)-1,3-oxazolin, 2-amino-4-(2’R)(2’-hydroxy octyl)-5-(carbomethoxyheptyl)-1,3-oxazoline and 2-amino-4-pentyl-5-[(8’R)-8’-hydroxy(carbomethoxy decyl)-1,3-oxazolineshowed vasodilation and antihypertensive properties. Furthermore, a computational analysis of physicochemical parameters revealed that the most of the compounds possessed drug-like attributes. Using Bioinformatics approach, we found a correlation between the observed and predicted antimicrobial activities.
- Ahmad, Anis,Ahmad, Aiman,Sudhakar, Raja,Varshney, Himani,Subbarao, Naidu,Ansari, Saba,Rauf, Abdul,Khan, Asad U.
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- Factors influencing orientations of covalently-attached and doped aromatic groups in stretched polyethylene films
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Linear polarizations have been measured for covalently attached and doped 9-anthryl and 1-pyrenyl groups residing in interior sites of stretched polyolefinic films. The influences of polymer crystallinity, the concentration of aromatic groups and the length of the substituents attached to doped molecules or of the tethers to polymer chains of covalently attached species on the degree of polarization have been explored. The results demonstrate the utility of comparing orientational parameters from doped and covalently attached groups in analyzing the factors responsible for stretch-induced orientation. The anthryl and pyrenyl groups prefer to reside in interfacial regions more than amorphous regions even before film stretching, and the specificity of their orientations is determined by the nature of interactions with surrounding polymer chains. The magnitudes of orientation factors are dependent on polymer crystallinity and substituent or tether length, but are independent of aromatic group concentrations as long as they are low. There are significant differences between the orientations of doped and covalently attached groups of the same type due to the inability of the latter to translocate between site types during film stretching. The results, as interpreted in the context of current theories, demonstrate the necessity of crystallite surfaces (i.e., interfacial sites), but not stretching-induced translocation, for selective orientation of aromatic groups along the axis of stretching.
- Wang, Caihua,Xu, Jinqi,Weiss, Richard G.
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- Total Synthesis of Four Isomers of the Proposed Structures of Cryptorigidifoliol K
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The first asymmetric convergent total synthesis of four isomers of proposed structures of cryptorigidifoliol K (1a, 1b, 1c, and 1d) has been achieved from commercially available starting materials. The key steps in this synthesis involve tandem isomerization followed by a C-O and C-C bond-forming reaction for the construction of trans-2,6-disubstituted dihydropyran, iodolactonization, isomerization of terminal alkene, and cross-metathesis reaction. The large discrepancies in the spectroscopic data (1H NMR) of synthetic cryptorigidifoliol K from the natural product suggest that the structure of the natural cryptorigidifoliol K requires revision.
- Reddy, G. Sudhakar,Padhi, Birakishore,Bharath, Yada,Mohapatra, Debendra K.
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- Stereochemistry of Deconjugative Alkylation of Ester Dienolates. Stereospecific Total Synthesis of the Litsenolides
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Deconjugative protonations, alkylations, and aldol condensations of the dienolates from (Z)-2-alkenoates give the corresponding (E)-3-enoate products, whereas dienolates from (E)-2-enoates give mainly the (Z)-3-enoate products.These generalizations are exploited in stereospecific total syntheses of litsenolides A2, B2, and C2.
- Kende, Andrew S.,Toder, Bruce H.
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- Designing and synthesis of novel antimicrobial heterocyclic analogs of fatty acids
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Novel series of long chain isoxazole derivatives were designed as inhibitors of Cytochrome P450-14DM14a-demethylase from Candida albicans and ribosomal subunit of S12 protein from Escherichia coli. The novel compounds (6-10) were synthesized through 1,3-dipolar cycloaddition of nitrile oxide to long chain alkynoic acid and alkenyl/hydroxyalkenyl esters and tested for their antimicrobial activity by disk diffusion assay and MIC by broth micro dilution method. After predicting the hidden potential and drug-likeness of compounds, ADMET-related descriptors were also calculated to predict pharmacokinetic properties. Molecular docking studies have been performed to evaluate possible mode of action of molecules in active site of receptor. Compounds (9 and 10) showed excellent antimicrobial activity nearly equivalent to the control compounds.
- Ahmad, Aiman,Ahmad, Anis,Varshney, Himani,Rauf, Abdul,Rehan, Mohd,Subbarao, Naidu,Khan, Asad U.
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- Synthesis and characterization of DNA-modified silicon (111) surfaces
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Hydrogen-terminated Si(111) surfaces are modified by attachment of oligodeoxynucleotides and characterized with respect to DNA surface density, chemical stability, and DNA hybridization binding specificity. Surface functionalization employs the reaction of ω-unsaturated alkyl esters with the Si(111) surface using UV irraaiation. Cleavage of the ester using potassium tert-butoxide yields a carboxyl-modified surface, which serves as a substrate for the attachment of DNA by means of an electrostatically adsorbed layer of polylysine and attachment of thiol-modified DNA using a heterobifunctional cross-linker. The resultant DNA-modified surfaces are shown to exhibit excellent specificity and chemical stability under the conditions of DNA hybridization. This work provides an avenue for the development of devices in which the exquisite binding specificity of biomolecular recognition is directly coupled to semiconductor devices.
- Strother, Todd,Cai, Wei,Zhao, Xinsheng,Hamers, Robert J.,Smith, Lloyd M.
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- Kinetics of epoxidation of alkyl esters of undecylenic acid: Comparison of traditional routes vs. Ishii-Venturello chemistry
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Epoxidation of undecylenic acid and its methyl and ethyl esters with aqueous H2O2 was carried out by using different traditional routes, ion exchange resin, and the newly developed synergistic usage of heteropoly acids and phase transfer catalysis in a biphasic system. The so-called Ishii-Venturello chemistry was employed to develop a kinetic model. Interesting selectivities are obtained.
- Yadav,Satoskar
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- Synthesis from Undecylenic Acid of Macroheterocycles with Diacylhydrazine and Ester Fragments
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A three-step synthesis of potentially biologically active 30- and 32-membered macroheterocycles with esters and acylhydrazines starting from methyl undecylenate was developed based on [1+1]-condensation of intermediate tetraesters, i.e., bis(10′ -methoxy-10′-oxodecyl)- or bis(11′-methoxy-11′ -oxoundecyl)hexanedioate, with hydrazine hydrate. The structures of the synthesized compounds were confirmed using IR and NMR spectroscopy and mass spectrometry.
- Mingaleeva,Yakovleva,Ishmuratov, G. Yu.
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- Synthesis of fully alternating polycarbonate with low Tg from carbon dioxide and bio-based fatty acid
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The selective copolymerization of CO2 and an epoxide to form fully alternating polycarbonates is a great challenge via catalysis with the zinc-cobalt(iii) double metal cyanide complex [Zn-Co(iii) DMCC]. We describe the first perfectly alternating copolymerization of CO2 with a bio-based epoxide. The resultant polycarbonate had a low Tgs of -38 to -44 °C and two end hydroxyl groups, which were then used to initiate ring-opening polymerization of l-lactide via metal-free catalysis, affording a biodegradable triblock copolymer. This study provides a new platform copolymer for making various advanced polymers with biodegradable properties. This journal is the Partner Organisations 2014.
- Zhang, Ying-Ying,Zhang, Xing-Hong,Wei, Ren-Jian,Du, Bin-Yang,Fan, Zhi-Qiang,Qi, Guo-Rong
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- An enzymatic approach to bifunctional chelating agents
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Bifunctional chelating agents (BFCAs) combine the complexing properties of a multidentate ligand with the presence of a free reactive functional group, mainly devoted to conjugation purposes. Indeed, products obtained by conjugation of a BFCA to a biomolecule and coordination of a suitable metal ion are widely applied in medicine nowadays as diagnostic and therapeutic agents. BFCAs are generally prepared through multi-step syntheses and with extensive application of protection-deprotection strategies, due to the large number of functional groups involved. Hydrolytic enzymes, with their unique chemoselectivity, provided the best results in the preparation of three different BFCAs based on very useful and well known ligand platforms. This journal is the Partner Organisations 2014.
- Minazzi, Paolo,Lattuada, Luciano,Menegotto, Ivan G.,Giovenzana, Giovanni B.
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- Methyl Radical Initiated Kharasch and Related Reactions
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An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-tert-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N2) or volatile (acetone and methyl halide) thereby facilitating greatly product purification by either flash column chromatography or distillation. In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 minutes under normal atmosphere) and a low excess of the radical precursor reagent (2 equivalents) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-tert-butyl peroxyoxalate (DTBPO) is also demonstrated as alternative source of tert-butoxyl radicals to initiate these reactions under identical conditions which gives gaseous by-products (CO2). (Figure presented.).
- Tappin, Nicholas D. C.,Renaud, Philippe
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supporting information
p. 275 - 282
(2020/12/07)
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- Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes
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Bio-derived furan- and diacid-derived cyclic carbonates have been synthesized in high yields from terminal epoxides and CO2. Furthermore, four highly substituted terpene-derived cyclic carbonates were isolated in good yields with excellent diastereoselectivity in some cases. Eleven new cyclic carbonates derived from 10-undecenoic acid under mild reaction conditions were prepared, providing the corresponding carbonate products in excellent yields. The catalyst system also performed the conversion of an epoxidized fatty acid n-pentyl ester into a cyclic carbonate under relatively mild reaction conditions (80 °C, 20 bar, 24 h). This bis(cyclic carbonate) was obtained in high yields and with different cis/trans ratios depending on the co-catalyst used. An allyl alcohol by-product was only observed as a minor product when bis(triphenylphosphine)iminium chloride was used as co-catalyst. Finally, two cyclic carbonates were used as building blocks for the preparation of non-isocyanate poly(hydroxy)urethanes by reaction with 1,4-diaminobutane.
- Martínez, Javier,de la Cruz-Martínez, Felipe,Martínez de Sarasa Buchaca, Marc,Fernández-Baeza, Juan,Sánchez-Barba, Luis F.,North, Michael,Castro-Osma, José A.,Lara-Sánchez, Agustín
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p. 460 - 468
(2021/04/06)
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- Rhodium-Catalyzed β-Dehydroborylation of Silyl Enol Ethers: Access to Highly Functionalized Enolates
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An efficient rhodium-catalyzed β-dehydroborylation of aldehyde-derived silyl enol ethers (SEEs) with bis(pinacolato)diboron (B2pin2) is disclosed. The borylation reactions proceeded well with alkyl- and aryl-substituted SEEs, affording a wide array of valuable functionalized β-boryl silyl enolates with high efficiency and excellent stereoselectivity. Moreover, the borylated products, through versatile carbon–boron bond transformations, were readily converted into diverse synthetically useful molecules, including α-hydroxy ketones, functionalized SEEs, and gem-difunctionalized aldehydes.
- Li, Jie,Li, Ruoling,Yang, Wen,Zhao, Pei,Zhao, Wanxiang
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supporting information
p. 9580 - 9585
(2021/12/14)
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- Cobalt-Catalyzed Intermolecular Markovnikov Hydroamination of Nonactivated Olefins: N2-Selective Alkylation of Benzotriazole
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Cobalt-catalyzed Markovnikov-selective hydroamination of nonactivated olefins was developed. Hydrogen atom transfer from a catalytically generated cobalt(III)-hydride complex to the olefins proceeded regioselectively, and the nucleophilic addition of benzotriazoles occurred selectively at their N2-positions. The synthetic utility of the obtained N2-alkylated benzotriazoles as stable amine protecting groups under various reaction conditions was demonstrated, and the products were also transformed into primary amines by zinc-mediated reduction.
- Yahata, Kenzo,Kaneko, Yuki,Akai, Shuji
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supporting information
p. 598 - 603
(2020/02/04)
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- Cyclopropanation of Terminal Alkenes through Sequential Atom-Transfer Radical Addition/1,3-Elimination
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An operationally simple method to affect an atom-transfer radical addition of commercially available ICH2Bpin to terminal alkenes has been developed. The intermediate iodide can be transformed in a one-pot process into the corresponding cyclopropane upon treatment with a fluoride source. This method is highly selective for the cyclopropanation of unactivated terminal alkenes over non-terminal alkenes and electron-deficient alkenes. Due to the mildness of the procedure, a wide range of functional groups such as esters, amides, alcohols, ketones, and vinylic cyclopropanes are well tolerated.
- Tappin, Nicholas D. C.,Michalska, Weronika,Rohrbach, Simon,Renaud, Philippe
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supporting information
p. 14240 - 14244
(2019/08/26)
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- Cobalt-Catalyzed C(sp2)-H Allylation of Biphenyl Amines with Unbiased Terminal Olefins
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Unactivated olefins usually react poorly in conventional alkenylation reactions. Their introduction via C-H activation is limited to aromatic acids. Herein, we disclose a C-H functionalization protocol of aromatic amines with unactivated olefins, which shows exclusive allylic selectivity for the distal ring of the biphenyl system by exploiting a readily available cobalt(II) catalyst. The allylation proceeds smoothly involving a broad set of unbiased olefins and biaryls, giving access to the functionalization of the biphenyl scaffold.
- Baccalini, Alessio,Vergura, Stefania,Dolui, Pravas,Maiti, Siddhartha,Dutta, Subhabrata,Maity, Soham,Khan, Farheen Fatima,Lahiri, Goutam Kumar,Zanoni, Giuseppe,Maiti, Debabrata
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supporting information
p. 8842 - 8846
(2019/11/11)
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- FLOUROALKYL, FLOUROALKOXY, PHENOXY, HETEROARYLOXY, ALKOXY, AND AMINE 1,4-BENZOQUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISORDERS
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Disclosed herein are compounds and methods of using such compounds for treating or suppressing oxidative stress disorders, including mitochondrial disorders, impaired energy processing disorders, neurodegenerative diseases and diseases of aging, or for modulating one or more energy biomarkers, normalizing one or more energy biomarkers, or enhancing one or more energy biomarkers, wherein the compounds are tocopherol quinone derivatives. Further disclosed are compounds, compositions, and methods for treatment of, or prophylaxis against, radiation exposure.
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Paragraph 0161; 0162
(2017/07/14)
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- METHOD FOR PRODUCING OMEGA-HYDROXY FATTY ACID ESTER AND PRECURSOR COMPOUND THEREOF
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Provided is a method for producing a compound represented by Formula (III) while the production of by-products due to, for example, dimerization of a raw material or isomerization of a double bond position is suppressed. The method is a method for producing omega-hydroxy fatty acid ester and a precursor compound thereof of Formula (III), in which an alcohol derivative and a carboxylic acid derivative are subjected to a metathesis reaction in the presence of a catalyst to obtain a compound of Formula (III), wherein the alcohol derivative is at least one selected from the group consisting of a compound of Formula (VI) and a compound of Formula (I), and the carboxylic acid derivative is at least one selected from the group consisting of a compound of Formula (VII) and a compound of Formula (II), wherein the case where the alcohol derivative is formed of a compound of Formula (I) and the carboxylic acid derivative is formed of a compound of Formula (II) is excluded,
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Paragraph 0099; 0100; 0102
(2016/07/27)
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- Catalytic cracking preparing 10-cavity and enanthaldehyde method
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The invention relates to a process for producing polyundecancylamide resin through castor oil and particularly relates to a method for preparing 10-undecenoic acid and heptanal through the castor oil in the process. The method comprises the following steps: ester interchange is performed on the castor oil and methyl alcohol to generate ricinic acid methyl ester; catalytic cracking is performed on the ricinic acid methyl ester to generate10-undecenoic acid methyl ester and heptanal; pressure-reduction rectification separation is performed on the 10-undecenoic acid methyl ester and heptana; saponification and acidification are performed on the 10-undecenoic acid methyl ester and heptana, so that 10-undecylenic acid is obtained; the ricinic acid methyl ester is mixed with water (or water vapor) according to the mass ratio of 1:(0.5-2), the mixture is preheated to 200-400 DEG C, and then is loaded into a cracking still filled with a catalyst, and cracking is performed at the temperature of 400-500 DEG C, so that the 10-undecenoic acid and heptanal are generated. According to the invention, due to catalytic action, the cracking temperature is reduced greatly, so that side reactions such as polymerization and isomerization of the double bond, the secondary cracking of a product and coking are reduced, and the yield of the 10-undecenoic acid and heptanal is improved greatly.
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Paragraph 0028-0029
(2017/03/08)
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- Selective conversion of castor oil derived ricinoleic acid methyl ester into jet fuel
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The selective conversion of ricinoleic acid methyl ester into jet fuel was realized through the integration of feedstock properties and rational catalytic design strategy. A unique hydroxyl group in the ricinoleic acid chain induced a special thermal rearrangement reaction in medium chain fatty acid methyl ester (FAME) and heptanal formation. Such a reaction was used as the starting point for our proposed process. Methyl 10-undecenoate was converted into a branched paraffin with limited carbon loss. Both Pt/Al2O3 and Pt/ZSM-22 catalysts resulted in selective hydrogenation (with limited decarbonylation) and hydro-isomerization (with negligible cracking), respectively. Another product, heptanal, was also converted into jet fuel through selective dimerization and hydrodeoxygenation with a supported amine and commercially available Pt/Al2O3 catalyst, respectively. With the right integration of these technologies, the carbon selectivity in the castor oil to jet fuel process is as high as 90%.
- Zhou, Yuping,Huang, Yong,Fang, Yunming,Tan, Tianwei
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p. 5180 - 5189
(2016/10/09)
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- Agent having neurotrophic factor-like activity
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The present invention provides a pharmaceutical agent having high safety and a neurotrophic factor-like activity, which contains, as an active ingredient, any one compound included in fatty acids each having 8 carbon atoms (C8) or having 10 carbon atoms (C10) to 12 carbon atoms (C12) or fatty acid esters thereof, such as 3,7-dimethyloctanoic acid ethyl ester, geranicacidethyl ester, and the like, eachof whichhas 8 carbonatoms (C8), decanoic acid methyl ester, trans-2-decenoic acid, trans-2-decenoic acid methyl ester, trans-2-decenoic acid ethyl ester, trans-2-decenoic acid-2-decenyl ester, trans-2-decenoic acid cyclohexyl ester, trans-2-decenoic acid isopropyl ester, trans-3-decenoic acid methyl ester, trans-9-decenoic acid methyl ester, and the like, each of which has 10 carbon atoms (C10), trans-10-undecenoic acid methyl ester, trans-10-undecenoic acid ethyl ester, and the like, each of which has 11 carbon atoms (C11), and dodecanoic acid, and the like, each of which has 12 carbon atoms (C12), or salts thereof or prodrugs thereof.
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Paragraph 0041-0042
(2016/01/25)
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- Aerobic Copper-Catalyzed O-Methylation with Methylboronic Acid
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The oxidative coupling of alkylboronic acids with oxygen nucleophiles offers a strategy for replacing toxic, electrophilic alkylating reagents. Although the Chan-Lam reaction has been widely applied in the arylation of heteroatom nucleophiles, O-alkylation with boronic acids is rare. We report a Cu-catalyzed nondecarboxylative methylation of carboxylic acids with methylboronic acid that proceeds in air with no additional oxidant. An isotope-labeling study supports an oxidative cross-coupling mechanism, in analogy to that proposed for Chan-Lam arylation.
- Jacobson, Clare E.,Martinez-Mu?oz, Noelia,Gorin, David J.
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p. 7305 - 7310
(2015/07/28)
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- Using N-nitrosodichloroacetamides to conveniently convert linear primary amines into alcohols
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The reported rearrangement of N-nitrosodichloroacetamides provides a practicalmethod for converting primary amines into primary alcohols. The reaction sequence is operationally simple, requires only a single purification, and is compatible with a number of common functional groups. Mechanistic studies of the nitrosylation and rearrangement reactions illustrate the increased utility of dichloroacetamides compared to various other amides for this transformation.
- Macarthur, Nicholas S.,Wang, Linshu,Mccarthy, Blaine G.,Jakobsche, Charles E.
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supporting information
p. 2014 - 2021
(2015/08/18)
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- A novel aromatic carbocation-based coupling reagent for esterification and amidation reactions
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A novel tropylium-based coupling reagent has been developed to facilitate the synthesis of a series of esters, amides, lactones and peptides under mild reaction conditions. Remarkably, this reagent can be used in catalytic amounts in conjunction with a sacrificial reagent, offering a new and efficient method for nucleophilic coupling reactions of carboxylic acids.
- Nguyen, Thanh V.,Lyons, Demelza J.M.
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supporting information
p. 3131 - 3134
(2015/06/17)
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- Improved protocol toward 1,3,4-oxadiazole-2(3H)-thiones and scale-up synthesis in the presence of SDS as a micelle promoted catalyst
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Convenient procedure for in situ cyclization of hydrazinecarbodithioate potassium salts to 1,3,4-oxadiazole-2(3H)-thiones under normal phase micellar media catalysis promoted by sodium dodecyl sulfate (SDS) as an anionic surfactant is reported. The main advantage of this procedure is to provide shorter reaction time for the completion of cyclization; scale-up synthesis is possible and the oxadiazoles were obtained in high to excellent yields (87-100%), making the protocol an attractive alternative to the available methods.
- Yildirim, Ayhan
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p. 473 - 478
(2015/06/30)
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- METHOD FOR SYNTHESIZING AN OMEGA-AMINO ACID OR ESTER FROM A MONOUNSATURATED FATTY ACID OR ESTER
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A method for synthesizing ω-amino-alkanoic acids or the esters thereof from natural unsaturated fatty acids passing through an intermediate ω-unsaturated nitrile compound. The method is simple to implement and, relative to known methods, avoids the environmental constraints and economic disadvantages resulting from the reaction by-products. The method includes synthesizing an ω-amino acid (ester) of formula R3OOC—(CH2)q—CH2NH2, in which R3 is H or an n-butyl radical and q is an integral index of between 2 and 13, from a monounsaturated fatty acid (ester) of formula (R1-CH═CH—(CH2)p-COO) xR2, in which x represents 1, 2 or 3, R1 is H or a hydrocarbon radical comprising from 4 to 11 carbon atoms and, where appropriate, a hydroxyl function, R2 is H or an alkyl radical comprising from 2 to 4 carbon atoms, and may contain one or more heteroatoms, and p is an integral index of between 2 and 11, including a reaction step of ammoniation.
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Paragraph 0092-0094
(2014/07/08)
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- Copper-catalyzed selective semihydrogenation of terminal alkynes with hypophosphorous acid
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A novel copper-catalyzed selective semihydrogenation of terminal alkynes using hypophosphorous acid as hydrogen donor took place efficiently to afford the corresponding alkenes in high yields. A broad range of substituted terminal aromatic and aliphatic alkenes, including terminal dienes and enynes bearing internal triple bonds, can be efficiently synthesized by this reaction.
- Cao, Huanyang,Chen, Tieqiao,Zhou, Yongbo,Han, Daoqing,Yin, Shuang-Feng,Han, Li-Biao
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p. 765 - 769
(2014/04/03)
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- Catalytic transesterification of cellulose in ionic liquids: Sustainable access to cellulose esters
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Catalytic transesterifications of cellulose were studied under homogeneous conditions using the ionic liquid 1-butyl-3-methylimidazolium chloride (BMIMCl) as a solvent. Cellulose was thus efficiently converted into cellulose esters employing various methyl esters and 10 mol% of 1,5,7-triazabicyclo[4.4.0]dec-5- ene (TBD) as catalyst. 1H NMR analysis of the products revealed up to 2.3 turnovers of the methyl esters per catalyst molecule, leading to degrees of substitution (DS) of up to 0.69. Although a comparatively low turnover number (TON) is observed, the developed methodology represents the first successful homogeneous catalytic reaction on cellulose. Furthermore, the new method is an important step forward in terms of sustainability, since the BMIMCl-DMSO mixture can be recycled and reused for the reaction, and toxic and corrosive chemicals commonly employed for cellulose esterification (such as anhydrides, acid chlorides and bromides, organic bases, all in overstoichiometric amounts) are avoided. To demonstrate the versatility of this transesterification, an aromatic (cellulose benzoate), an aliphatic (cellulose butyrate), and a fatty acid containing cellulose ester (cellulose 10-undecenoate) were prepared. Additionally, cellulose 10-undecenoate was successfully used for thiol-ene grafting onto reactions employing two thiols for efficient thiol-ene addition reactions. This journal is the Partner Organisations 2014.
- Schenzel, Alexander,Hufendiek, Andrea,Barner-Kowollik, Christopher,Meier, Michael A. R.
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p. 3266 - 3271
(2014/06/10)
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- Cross-metathesis of methyl 10-undecenoate with dimethyl maleate: An efficient protocol with nearly quantitative yields
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In this cross metathesis of the renewable raw material methyl 10-undecenoate with dimethyl maleate, an α,ω-difunctional product was produced. Detailed optimizations led to nearly quantitative yields of the desired product. The cross metathesis of methyl 10-undecenoate with methyl acrylate yielded high conversions of the substrate. The product was accessed under mild reaction conditions with the use of a small amount of a commercially available homogeneous ruthenium catalyst. The in situ synthesis of dimethyl maleate from maleic anhydride was also possible in this reaction system. This journal is the Partner Organisations 2014.
- Behr,Toepell,Harmuth
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p. 16320 - 16326
(2014/05/06)
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- Synthesis, characterization, and evaluation of 10-undecenoic acid-based epithio derivatives as multifunctional additives
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Novel epithio compounds from alkyl epoxy undecanoates (n-alkyl, C1, C4, and C6; isoalkyl, C3, C4, and C8) were synthesized using an ammonium thiocyanate in ionic liquid 1-methylimidazolium tetrafluoroborate/H2O (2:1) solvent system in 85-90% yields by gas chromatographic (GC) analysis. The synthesized products were characterized by 1H and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy (FTIR), gas chromatography, and GC mass spectral (GC-MS) analyses and evaluated for their antioxidant, extreme pressure (EP), and antiwear (AW) properties in three different base oils, namely, epoxy jatropha fatty acid n-butyl esters (EJB), di-2-ethylhexyl sebacate (DOS), and mineral oil (S-105). Among the synthesized products, n-butyl epithio undecanoate exhibited superior antioxidant property (229.2 °C) compared to butylated hydroxytoluene (BHT, 193.8 °C) in base oil DOS and comparable performance in EJB and S-105 base oils. All of the epithio derivatives exhibited significantly enhanced weld point for the base oils EJB and DOS at 2 wt % level and displayed moderate enhancement in S-105 base oil. Methyl epithio undecanoate at 0.6% concentration exhibited considerable improvement in the wear scar of DOS base oil. The synthesized epithio derivatives have potential as multifunctional additives in lubricant formulations.
- Geethanjali, Gorla,Padmaja, Korlipara V.,Sammaiah, Arukali,Prasad, Rachapudi B. N.
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p. 11505 - 11511
(2015/02/19)
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- NOVEL METHOD FOR PREPARING POLYOLS AND PRODUCTS OBTAINED
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The present invention relates to a method for preparing polyols of formula (I″) R′1 being H or an alkyl group, R″ being especially an alkyl group, A1, being an alkylene radical and R3, are being especially a group -A2-O—Y′, A2 being an alkylene radical and Y′ being especially H, said method especially comprising a step of epoxidation of a compound of formula R″1 being H or an alkyl group, A1 being defined as above in formula (I″) and R4 being especially a group -A2-O—Y1′, A2 being defined as above in formula (I″) and Y′1 being especially H, in order to obtain a compound of formula A1 being defined as above, R′″1 being H or an alkyl group and R5 being especially a group of formula -A2-O—Y2′, A2 being as defined above in formula (I″) and Y′2 being especially H,
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Page/Page column 23
(2013/02/28)
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- The mechanism of caseinolytic protease (ClpP) inhibition
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Catch me if you can: The ClpP protease mediates protein homeostasis and can be efficiently inhibited by β-lactones. A combination of molecular docking, mutagenesis, activity-based protein profiling, and kinetics studies now reveals the mechanism of ClpP inhibition. A hydrophobic pocket next to the active site allows binding of long aliphatic and aromatic residues. The preferred stereoisomer binds into the oxyanion hole. Copyright
- Gersch, Malte,Gut, Felix,Korotkov, Vadim S.,Lehmann, Johannes,B?ttcher, Thomas,Rusch, Marion,Hedberg, Christian,Waldmann, Herbert,Klebe, Gerhard,Sieber, Stephan A.
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supporting information
p. 3009 - 3014
(2013/04/23)
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- Removal of ruthenium using a silica gel supported reagent
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A solid-supported isocyanide ligand was developed to destroy active metathesis catalysts and to remove ruthenium byproducts from metathesis reactions. This method was able to significantly reduce the concentration of residual ruthenium from the organic products of several alkene and ene-yne metathesis reactions, under a variety of different conditions.
- French, Jonathan M.,Caras, Caley A.,Diver, Steven T.
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supporting information
p. 5416 - 5419
(2013/11/19)
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- Introducing catalytic lossen rearrangements: Sustainable access to carbamates and amines
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A new, highly efficient and environmentally benign catalytic variant of the Lossen rearrangement is described. Dimethyl carbonate (DMC) as green activation reagent of hydroxamic acids in presence of catalytic amounts of tertiary amine bases {1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), 1,8-biazabicyclo 5.4.0 undec-7-ene (DBU), 1,4-diazabicyclo[2.2.2]octane (DABCO), and triethylamine} and small quantities of methanol initiate the rearrangement. Methyl carbamates were obtained in good to moderate yields when aliphatic hydroxamic acids were employed in this catalytic Lossen rearrangement; under the same conditions aromatic hydroxamic acids yielded anilines. Notably, the mixture of DMC/methanol was recycled several times without observing decreased yields, thus minimizing the produced waste. Moreover, several other organic carbonates were successfully employed in the introduced catalytic Lossen rearrangement procedure. Copyright
- Kreye, Oliver,Wald, Sarah,Meier, Michael A. R.
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supporting information
p. 81 - 86
(2013/03/13)
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- Continuous flow oxidation of alcohols and aldehydes utilizing bleach and catalytic tetrabutylammonium bromide
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We report a method for the oxidation of a range of alcohols and aldehydes utilizing a simple flow system of alcohols in EtOAc with a stream of 12.5% NaOCl and catalytic Bu4NBr. Secondary alcohols are oxidized to ketones, aldehydes are oxidized directly to methyl esters in the presence of methanol, and benzylic alcohols are oxidized to either benzaldehydes or methyl esters, depending on the conditions used. The reaction conditions are mild and generally provide complete conversion in 5-30 min.
- Leduc, Andrew B.,Jamison, Timothy F.
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supporting information; experimental part
p. 1082 - 1089
(2012/08/27)
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- Divergent process for C10, C11 and C12 ω-amino acid and α,ω-dicarboxylic acid monomers of polyamides from castor oil as a renewable resource
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Polyamides have great potentials for diverse applications and the present production of their monomers mostly relies on resources from fossil fuel. Starting from undecylenic acid, a natural resource, we have developed both divergent and efficient processes for C10, C11 and C 12 ω-amino acid and α,ω-dicarboxylic acid monomers of the polyamides.
- Koh, Moo-Hyun,Kim, Hyeonjeong,Shin, Nara,Kim, Hyun Su,Yoo, Dongwon,Kim, Young Gyu
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experimental part
p. 1873 - 1878
(2012/08/07)
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- Synthesis of donor-σ-perylenebisimide-acceptor molecules having PEG swallowtails and sulfur anchors
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Donor-σ-Acceptor (D-σ-A) molecules, arrayed in a monolayer between electrodes, can serve as molecular rectifiers. Using perylene-3,4,9,10-tetracarboxylic bisimide (PBI) as the acceptor allows the attachment of the donor group to one imide nitrogen and a solubilizing swallowtail, normally a long (e.g., C19) alkane connected at midchain, on the other. Such an alkyl tail facilitates the formation of Langmuir-Blodgett (LB) monolayers. We have employed several modified swallowtails to make new D-σ-A molecules: poly(ethylene glycol) (PEG) swallowtails with 6 ether oxygens or with 4 ether oxygens to promote hydrophilicity in orienting LB monolayers, and alkyl swallowtails ending with sulfur anchors (thioacetate, thiol, or methyl disulfide) to stabilize attachment of the D-σ-A molecules to gold electrodes. The preparation and characterization of D-σ-A molecules containing combinations of these swallowtails with pyrene, ferrocene, and tetramethylphenylenediamine donor groups is described.
- Kota, Rajesh,Samudrala, Ramakrishna,Mattern, Daniell Lewis
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p. 9641 - 9651
(2013/01/15)
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- METHOD FOR THE SYNTHESIS OF AN OMEGA-AMINO ACID OR ESTER STARTING FROM A MONOUNSATURATED FATTY ACID OR ESTER
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The invention relates to a method for the synthesis of ω-amino alkanoic acids or esters thereof starting from unsaturated natural fatty acids passing through an ω-unsaturated nitrile intermediate compound.
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Page/Page column 8
(2011/10/04)
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- Benzophenone-containing fatty acids and their related photosensitive fluorescent new probes: Design, physico-chemical properties and preliminary functional investigations
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Hydrophobic photoaffinity labeling is a powerful strategy to identify hydrophobic segments within molecules, in particular membrane proteins. Here we report the design and synthesis of a novel family of fluorescent and photosensitive lipid tools, which have a common amino acid scaffold functionalized by three groups: (i) a first fatty acid chain grafted with a photoactivatable benzophenone moiety (Fatty Acid BenzoPhenone, FABP), (ii) a second fatty acid chain to ensure anchoring into a half-bilayer or hydrophobic environment, and (iii) a fluorescent carboxytetramethylrhodamine headgroup (CTMR) to detect the photolabeled compound. We present data of the synthesis and characterization of three lipid tools whose benzophenone ring is situated at various distances from the central scaffold. We could therefore establish structure/properties relationships dependent upon the depth of insertion of benzophenone into the membrane. Our lipid tools were extensively characterized both physico- and bio-chemically, and we assessed their functionality in vitro using bacterioRhodopsin (bR). We thus provide the scientific community with novel and reliable tools for the identification and study of hydrophobic regions in proteins.
- Hilbold, Beno?t,Perrault, Marie,Ehret, Christophe,Niu, Song-Lin,Frisch, Beno?t,Pécheur, Eve-Isabelle,Bourel-Bonnet, Line
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experimental part
p. 7464 - 7473
(2012/01/06)
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- METHOD FOR THE SYNTHESIS OF DIACIDS OR DIESTERS FROM NATURAL FATTY ACIDS AND/OR ESTERS
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The invention relates to a process for the synthesis of diacids or diesters of general formula ROOC—(CH2)x—COOR, in which n is an integer between 5 and 14, R is either H or an alkyl radical of 1 to 4 carbon atoms, from natural long-chain monounsaturated fatty acids or esters including at least 10 adjacent carbon atoms per molecule of the general formula CH3—(CH2)n—CHR1—CH2—CH═CH—(CH2)p—COOR, in which R is H or an alkyl radical with 1 to 4 carbon atoms, R1 is either H or OH, and n and p, which are equal or different and are indices between 2 and 11. The method comprises: during a first step, converting the natural fatty acid or ester by pyrolysis or by ethenolysis, into a ω-monounsaturated fatty acid or ester of the general formula CH2═CH—(CH2)m—COOR, in which m is equal to p or p+1, depending on the nature of the processed fatty acid/ester and the conversion used; during a second step, submitting the product thus obtained to a metathesis or homometathesis reaction for obtaining a compound of the general formula ROOC—(CH2)m—CH═CH—(CH2)m—COOR, or cross-metathesis with a compound of formula R2OOC—(CH2)r—CH═CH—R3, in which R2 is either H or an alkyl radical front with 1 to 4 carbon atoms, r is either 0 or 1 or 2 and R3 is H, CH3 or COOR2, thus defining a cyclic or molecule or not, in order to obtain an unsaturated compound of the general formula ROOC—(CH2)m—CH═CH—(CH2)r—COOR2, and during a third step, converting the unsaturated compound into a saturated compound by hydrogenation of the double bond.
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Page/Page column 6
(2010/12/29)
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- AGENT HAVING NEUROTROPHIC FACTOR-LIKE ACTIVITY
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The present invention provides a pharmaceutical agent having high safety and a neurotrophic factor-like activity, which contains, as an active ingredient, any one compound included in fatty acids each having 8 carbon atoms (C8) or having 10 carbon atoms (C10) to 12 carbon atoms (C12) or fatty acid esters thereof, such as 3,7-dimethyloctanoic acid ethyl ester, geranicacidethyl ester, and the like, eachof whichhas 8 carbonatoms (C8), decanoic acid methyl ester, trans-2-decenoic acid, trans-2-decenoic acid methyl ester, trans-2-decenoic acid ethyl ester, trans-2-decenoic acid-2-decenyl ester, trans-2-decenoic acid cyclohexyl ester, trans-2-decenoic acid isopropyl ester, trans-3-decenoic acid methyl ester, trans-9-decenoic acid methyl ester, and the like, each of which has 10 carbon atoms (C10), trans-10-undecenoic acid methyl ester, trans-10-undecenoic acid ethyl ester, and the like, each of which has 11 carbon atoms (C11), and dodecanoic acid, and the like, each of which has 12 carbon atoms (C12), or salts thereof or prodrugs thereof.
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- New methodology for the conversion of epoxides to alkenes
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Epoxides have been transformed in good yields to alkenes by a process involving (i) ring-opening of the epoxide with 2-mercaptobenzothiazole, (ii) oxidation of the derived ss-hydroxy thioethers to the corresponding sulfones, and (iii) thermal or base-promoted fragmentation of these sulfones to alkenes. The stereochemistry of the starting epoxide is transfer-red faithfully to the alkene product, because of the SN2 epoxide ring-opening reactions and the antiperiplanar SO2 elimination reaction of the ss- alkoxysulfinate intermediates. This methodology may form the basis of a new protecting group strategy for alkenes.
- Wu, Feng-Ling,Ross, Benjamin P.,McGeary, Ross P.
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scheme or table
p. 1989 - 1998
(2010/06/15)
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- Palladium-catalyzed allylic acyloxylation of terminal alkenes in the presence of a base
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"Chemical Equation Presentation" The efficiency and the selectivity of the Pd-catalyzed oxidation, in carboxylic acids, of terminal alkenes are strongly improved in the presence of a base. The methodology is particularly well adapted for the oxidation of homoallylic alcohols, for which the resulting acyloxylated products are obtained selectively as E-isomers in fair to good yields. 2010 American Chemical Society.
- Thiery, Emilie,Aouf, Chahinez,Belloy, Julien,Harakat, Dominique,Bras, Jean Le,Muzart, Jacques
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supporting information; experimental part
p. 1771 - 1774
(2010/05/01)
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- Alkenyl and alkenoyl amphiphilic derivatives of d-xylose and their surfactant properties
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Unsaturated fatty alkyl xylosides and the corresponding 1-O-acyl esters were prepared. Critical micellar concentrations, surface tension areas per molecule and foaming value of some of these new amphiphilic compounds have been determined.
- Damez, Celine,Bouquillon, Sandrine,Harakat, Dominique,Henin, Francoise,Muzart, Jacques,Pezron, Isabelle,Komunjer, Ljepsa
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p. 154 - 162
(2007/10/03)
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- C-GLYCOLIPIDS WITH ENHANCED TH-1 PROFILE
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The invention is directed to novel synthetic C-glycolipids that selectively induce a ThI -type immune response characterized by enhanced IL- 12 secretion and increased activation of dendritic cells. The compounds of the invention are thereby useful in treating infections, cancers, cell proliferative disorders, and autoimmune diseases, both directly and as adjuvants.
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Page/Page column 35
(2008/06/13)
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- Selective esterification of aliphatic carboxylic acids in the presence of aromatic carboxylic acids over monoammonium salt of 12-tungstophosphoric acid
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Monoammonium salt of 12-tungstophosphoric acid [(NH4)H 2PW12O40] was found to be a practical and useful heterogeneous catalyst for an efficient and selective esterification of aliphatic carboxylic acids with alcohols in the presence of aromatic carboxylic acids. The heteropoly acid-based heterogeneous catalyst has the advantages of a simple workup procedure, water insolubility, and good activity. Copyright Taylor & Francis LLC.
- Giri,Prabhavathi Devi,Gangadhar,Narasimha Rao,Lingaiah,Sai Prasad,Prasad
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- Facile oxidative conversion of alcohols to esters using molecular iodine
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A simple, efficient, and high-yield procedure for the oxidative conversion of alcohols to various types of esters and ketones, with molecular iodine and potassium carbonate was successfully carried out.
- Mori, Naoshi,Togo, Hideo
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p. 5915 - 5925
(2007/10/03)
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- Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide
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The synthesis of four novel compounds, (i) [(11-{[2-(3-nitrophenyl)-4-oxo- 1,3-thiazolidin-3-yl]amino}-11-oxoundecyl)sulfanyl]acetic acid (4), (ii) N-[5-methyl-2-(3-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]undec-10-enamide (5), (iii) 2-[(11-{[5-methyl-2-(3-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]amino}-11- oxoundecyl)sulfanyl]propanoic acid (6) and (iv) 3-[(11-{[2-(3-nitrophenyl)-4- oxo-1,3-thiazinan-3-yl]amino}-11-oxoundecenyl) sulfanyl]propanoic acid (8) from 10-undecenoic acid hydrazide (1) via m-nitrobenzaldehyde-10-undecenohydrazone (2) using mercaptoacetic acid in (i), 2-mercaptopropionic acid in (ii and iii) and 3-mercaptopropionic acid in (iv) is described. The uncyclized products, ({11-[(2E)-2-(3-nitrobenzylidene)hydrazino]-11-oxo-undecyl}sulfanyl)acetic acid (3) and 3-({11-[(2E)-2-(3-nitrobenzylidene)hydrazino]-11-oxoundecyl}sulfanyl) propanoic acid (7) are also obtained in (i) and (iv), respectively. The hydrazones (2), (3) and (7) exist in two conformers as synperiplanar and antiperiplanar. Structural assignment, stereochemistry and biological assays are discussed.
- Rahman, V.P. Mujeebur,Mukhtar, Sayeed,Ansari, Wajid Husain,Lemiere, Guy
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p. 173 - 184
(2007/10/03)
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- Preparation and characterization of cyclic-ketone derivatives of methyl undec-10-enoate and their cyclocondensation with mercaptoacetic acid
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Reaction of methyl undec-10-enoate 2 with cyclopentanone 1a affords two products, methyl 2-(2′-cyclopentanonyl)undec-10-enoate 3a and methyl 11-(2′-cyclopentanonyl)undecanoate 4a. Similarly, the reaction of cyclohexanone 1b gives two products 3b and 4b. Compounds 4a and 4b on further reaction with mercaptoacetic acid and ammonium carbonate yield the products 5a and 5b, respectively. Products have been characterized by elemental analysis and spectral data. Compounds 3a, b, 4a, b and 5a,b have been tested for antimicrobial activity. The compounds 3a,b and 4a,b show negative results at 100 μg/mL whereas the compounds 5a,b show positive results at 100 μg/mL.
- Rauf, Abdul,Jahan, Refat
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p. 1644 - 1648
(2007/10/03)
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