- Undec-10-enoic Acid in the Synthesis of Macroheterocycles Containing Hydrazide and Ester Fragments
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Four potentially biologically active 31-, 32-, and 33-membered macroheterocycles with ester and hydrazide fragments have been synthesized by [1 + 1]-condensation of ethane-1,2-diyl bis(10-oxoundecanoate) with malonic, glutaric, L-(+)-tartaric, and pyridine-2,6-dicarboxylic acid dihydrazides. The product structure has been confirmed by IR, NMR, and mass spectra.
- Mingaleeva,Yakovleva,Salakhutdinov,Tolstikov,Ishmuratov, G. Yu.
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- Thiol-ene vs. ADMET: A complementary approach to fatty acid-based biodegradable polymers
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The increasing need for biodegradable polymers in medical applications, attempts to use renewable resources instead of fossil resources for material synthesis, and highly efficient polymerization methods that meet the requirements of green chemistry draw attention to fatty acid-based biodegradable polymers. In the present study, we have prepared a set of anhydride and ester functional biodegradable polymers from undec-10-enoic acid via ADMET polymerization reactions and/or thiol-ene click reactions. The efficiency of these polymerization methods and the thermal, as well as hydrolytic, stability properties of the polymers were evaluated and compared to each other. The results reveal that the polymers exhibit melting points in the range 44-58°C, which is higher than physiological temperature, and that polyanhydrides degrade considerably faster in solution than structurally similar polyesters.
- Tueruen, Oguz,Meier, Michael A. R.
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- Photo- and Metallo-responsive N-Alkyl α-Bisimines as Orthogonally Addressable Main-Chain Functional Groups in Metathesis Polymers
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N-alkyl α-bisimines were employed as main-chain functional groups in acyclic diene metathesis (ADMET)-polymers, conferring dual responsiveness for the controlled switching of the polymeric particle shape with light and metal ions. Photochemical Z/E-isomerization leads to a significant and reversible change in hydrodynamic volume, thus introducing simple imines as novel photoswitches for light-responsive materials. Mild imine-directed CH activation by Pd(OAc)2 is demonstrated as a new single-chain nanoparticle (SCNP) folding process, enabling a controlled atom- and step-economic SCNP synthesis. The combination of light- and metallo-responsiveness in the same polymer provides the ability for orthogonal switching, a valuable tool for advanced functional material design.
- Greb, Lutz,Mutlu, Hatice,Barner-Kowollik, Christopher,Lehn, Jean-Marie
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- Diversely substituted polyamide structures through thiol-ene polymerization of renewable thiolactone building blocks
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A thiolactone derivative of 10-undecenoic acid was used as a renewable AB′ monomer for the one-pot synthesis of diversely substituted polyamide structures, containing amide moieties both in the polymer backbones and in their side chains. Nucleophilic aminolysis of the thiolactone entity liberates a thiol, which further reacts in a stepwise thiol-ene photopolymerization reaction. Using different primary amines, several structurally diverse polyamides, with physical properties dependent on the length and chemical identity of the side chain, were obtained. Postpolymerization oxidation of the sulfide linkages in the polymer backbone to their corresponding sulfoxides and sulfones altered the material, with the degree of oxidation having an impact on the final mechanical properties. Furthermore, this mild and straightforward polymerization procedure was applied for the synthesis of functional polymer networks.
- Goethals, Fabienne,Martens, Steven,Espeel, Pieter,Van Den Berg, Otto,Du Prez, Filip E.
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- Immobilization of catalytic virus-like particles in a flow reactor
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A functional microfluidic reactor is constructed by the immobilization of gold containing virus-based protein cages that catalyze the reduction of nitro-arenes with high efficiency.
- Liu,Yang,Traulsen,Cornelissen
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- Carboxylic acid- and ester-functionalized siloxane scaffolds on glass studied by broadband sum frequency generation
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Broadband sum frequency generation has been used to characterize glass surfaces functionalized with siloxanes containing terminal carboxylic acid and ester functional groups. ??-Ester silanes can be used in the preparations of ester-functionalized glass surfaces, which yield acid-functionalized surfaces via hydrolysis. This general methodology can be used in environmental, biochemical, or materials science surface chemistry to generate surfaces with tunable physical and chemical properties. Definitive characterization of these carboxylate-functionalized glass surfaces can be performed in the C-H vibrational frequency region using sum frequency generation.
- Voges, Andrea B.,Al-Abadleh, Hind A.,Musorrafiti, Michael J.,Bertin, Paul A.,Nguyen, SonBinh T.,Geiger, Franz M.
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- Synthesis and crystal structure of a meso-decene-BODIPY dye as a functional bright fluorophore for silicone matrices
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A meso-decene-BODIPY dye was synthesized and conjugated to a polydimethylsiloxane. Fluorescence properties of the obtained polymer drastically changed in different solvents. The polymer showed an unusual for other siloxane polymers trend to structuration.
- Pakhomov, Alexey A.,Mironiuk, Veronika B.,Kononevich, Yuriy N.,Korlyukov, Alexander A.,Volodin, Alexander D.,Pryakhina, Tatyana A.,Martynov, Vladimir I.,Muzafarov, Aziz M.
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- Chromium(VI) binding to functionalized silica/water interfaces studied by nonlinear optical spectroscopy
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Organic adlayers can significantly alter the interactions of environmentally relevant surfaces with their surroundings. We present the first second harmonic and broadband sum frequency generation (SHG and BBSFG) study that illustrates how organic surface functional groups can control the mobility of the priority pollutant chromium(VI) in soil: Cr(VI) binds to ester- and acid-functionalized surfaces but not to alkane-functionalized surfaces. The implications with respect to toxic metal transport across organic adlayers at liquid-solid interfaces are that aqueous Cr(VI) can be retained by polar groups common in biopolymers but not by hydrophobic groups common in surfactants. Copyright
- Al-Abadleh, Hind A.,Voges, Andrea B.,Bertin, Paul A.,Nguyen, SonBinh T.,Geiger, Franz M.
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- Infrared reflection-absorption study of ordering and hydrogen bonding within chiral and nonchiral self-assembled monolayers on gold
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Ordering processes in chiral and racemic monolayers of three phenylalanyl-substituted ω-thiol alkanoic acids on gold have been investigated with the use of infrared reflection absorption spectroscopy. For chiral molecules, packing is influenced by both hydrogen-bonding interactions between the end groups at the air/monolayer interface and the length of the spacer chain within the monolayer. Results for a mixed monolayer of octadecylmercaptane and phenylalanyl-substituted ω-thiol docosanoic acid indicate that formation of large islands of either one of the compounds can be excluded. For a racemic monolayer of phenylalanyl-substituted ω-thiol undecanoic acid, a dense, yet unregular, packing is observed.
- Nissink,Van Der Maas
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- Synthesis of borondipyrromethene (BODIPY)-labeled sphingosine derivatives by cross-metathesis reaction
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A new efficient and flexible synthesis of fluorescently labeled sphingosine derivatives from commercially available Garner aldehyde (8) is described. For this, appropriate alkenylated borondipyrromethene (BODIPY) dyes were synthesized and used for the first time in a cross-metathesis reaction, the key step of the approach. The labeled sphingosines with appropriate chain length were accepted as substrates by sphingosine kinases (SPHKs), yielding the corresponding phosphorylated products. One of these derivatives (11d) was identified as the first reported selective substrate for SPHK-1.
- Peters, Carsten,Billich, Andreas,Ghobrial, Michael,Hoegenauer, Klemens,Ullrich, Thomas,Nussbaumer, Peter
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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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- Full-spectrum selective reflection annular side chain liquid crystal oligomer film and preparation method thereof
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The invention discloses a full-spectrum selective reflection annular side chain liquid crystal oligomer film and a preparation method thereof. The preparation method comprises the following steps: respectively carrying out graft copolymerization on a chiral liquid crystal monomer and an achiral rod-like monomer or two chiral liquid crystal monomers and annular polymethyl hydrogen-containing siloxane to construct the full-spectrum selective reflection annular side chain liquid crystal oligomer film, the structural formula is shown as a formula I. The cyclic side chain liquid crystal oligomer can realize full-spectrum selective reflection in the heating process; at room temperature, the annular side chain liquid crystal oligomer film can realize full-spectrum selective reflection along with the change of an incident angle. The cyclic side chain liquid crystal oligomer prepared by the method has dual characteristics that dynamic full-spectrum selective reflection changes along with temperature and incident angle, and has a wide application prospect in the optical field, the preparation process is safe to operate, and reaction conditions are mild.
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Paragraph 0116; 0121-0123
(2021/08/06)
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- Synthesis of N-trifluoromethyl amides from carboxylic acids
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Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.
- Flavell, Robert R.,Liu, Jianbo,Parker, Matthew F. L.,Toste, F. Dean,Wang, Sinan,Wilson, David M.
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supporting information
p. 2245 - 2255
(2021/08/12)
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- Wavelength-Orthogonal Photocleavable Monochromophoric Linker for Sequential Release of Two Different Substrates
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A wavelength-orthogonal photocleavable monochromophoric linker was developed that is based on a 3-acetyl-9-ethyl-6-methylcarbazole (AEMC) moiety substituted at both the phenacyl and benzylic positions with different carboxylic acids. The different carboxylic acids were released sequentially upon irradiation with light of λ ≥ 365 nm and λ ≥ 290 nm, respectively.
- Venkatesh, Yarra,Chaudhuri, Amrita,Mondal, Saugat,Shah, Sk. Sheriff,Singh, N. D. Pradeep
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p. 295 - 299
(2020/01/02)
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- Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters
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We report herein an Ir-catalyzed intermolecular amino group transfer to β-keto esters (amides) to access α-aminocarbonyl products with excellent chemoselectivity. The key strategy was to engineer electrophilicity of the putative Ir-nitrenoids by tuning electronic property of the κ2-N,O chelating ligands, thus facilitating nucleophilic addition of enol π-bonds of 1,3-dicarbonyl substrates.
- Lee, Minhan,Jung, Hoimin,Kim, Dongwook,Park, Jung-Woo,Chang, Sukbok
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supporting information
p. 11999 - 12004
(2020/08/06)
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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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- Preliminary investigations into the synthesis and antimicrobial activities of boron-containing capsaicinoids
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This preliminary study reports on the synthesis of two new boron-capsaicin derivatives containing either a short or long chain aliphatic tail group using an iridium catalyzed hydroboration reaction with pinacolborane. The boronate ester groups reside on the terminal position of the tail group and are necessary for the bioactivity of these compounds. Indeed, both compounds showed considerable activity against two Gram-positive bacteria, including Vancomycin-resistant Enterococcus. Vancomycin is considered the last resort medication for the treatment of septicemia, and new antibacterial agents that can treat sepsis are of paramount importance. The more lipophilic boron compound with the longer aliphatic chain also showed antifungal activity against Saccharomyces cerevisiae.
- Ramsaywack, Sharwatie,Bos, Allyson,Vogels, Christopher M.,Gray, Christopher A.,Westcott, Stephen A.
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supporting information
p. 1065 - 1070
(2018/11/24)
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- Synthesis and cytotoxic evaluation of undecenoic acid-based oxime esters
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A series of undecenoic acid-based aldoxime esters have been synthesized using various substituted benzaldehydes and undecenoic acid. These oxime esters have been evaluated for their cytotoxic activities against HeLa, B16-F10, SKOV3, MCF7 and CHO-K1 normal cell line using MTT assay. Most of the synthesized compounds exhibit cytotoxicity. Particularly, 2,3-dimethoxy (IC50 value 12.48μM) and 3-methoxy (IC50 value 13.58μM) derivatives exhibit promising activities against SKOV3 cell lines. All the synthesized compounds are non-toxic towards the Chinese hamster ovary (CHO-K1) normal cell line.
- Vijayendar, Venepally,Kaki, Shiva Shanker,Vamshi Krishna,Misra, Sunil,Prasad,Jala, Ram Chandra Reddy
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p. 1015 - 1022
(2019/05/22)
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- Synthesis and biological evaluation of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thioglycosides
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In the present study, the synthesis of 1, 3, 4-thiadiazole-based thioglycosides were accomplished in good yields with employing a convergent synthetic route. The starting material 5-amino-1, 3, 4-thiadiazole-2-thiol and followed by a series of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thiols (4a–4j) were synthesized with different fatty acid chlorides. The glycosylation of compounds 4a–4j were achieved with trichloroacetimidate methodology. Antimicrobial and cytotoxicity activities of title compounds were evaluated. Among the entire compounds lauric acid and myristic acid derivatives showed good and moderate antimicrobial activity. In case of cytotoxicity results of compounds 8a–8j and 9a–9j, the acetate protected short chain (C6:0, C8:0, C10:0) compounds and the free hydroxyl long chain saturated (C16:0, C18:0) and unsaturated (C18:1, C22:1) compounds exhibited good activity against different cancer cell lines. Further, the free hydroxyl compounds 9a, 9c–9j did not show any toxicity towards normal CHO-K1 cell line whereas acylated compounds 8a–8j exhibited toxicity.
- Vudhgiri, Srikanth,Koude, Dhevendar,Veeragoni, Dileep Kumar,Misra, Sunil,Prasad,Jala, Ram Chandra Reddy
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supporting information
p. 3370 - 3373
(2017/07/07)
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- Selective α-Oxyamination and Hydroxylation of Aliphatic Amides
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Compared to the α-functionalization of aldehydes, ketones, even esters, the direct α-modification of amides is still a challenge because of the low acidity of α-CH groups. The α-functionalization of N?H (primary and secondary) amides, containing both an unactived α-C?H bond and a competitively active N?H bond, remains elusive. Shown herein is the general and efficient oxidative α-oxyamination and hydroxylation of aliphatic amides including secondary N?H amides. This transition-metal-free chemistry with high chemoselectivity provides an efficient approach to α-hydroxy amides. This oxidative protocol significantly enables the selective functionalization of inert α-C?H bonds with the complete preservation of active N?H bond.
- Li, Xinwei,Lin, Fengguirong,Huang, Kaimeng,Wei, Jialiang,Li, Xinyao,Wang, Xiaoyang,Geng, Xiaoyu,Jiao, Ning
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supporting information
p. 12307 - 12311
(2017/09/11)
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- RECYCLABLE CATALYSTS FOR CHLORINATION OF ORGANIC ACIDS AND ALCOHOLS
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The present invention discloses recyclable polymeric catalyst of Formula I, for chlorination of organic acids and alcohols using chlorinating agents such as carbonyl chloride, oxalyl chloride or thionyl chloride, wherein, ‘m’ on the pendent groups on polystyrene backbone can have values from 1 to 5 and R is the alkyl group ranging from C1 to C5.
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Paragraph 0108
(2017/10/10)
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- NMR-based assignment of isoleucine: Vs. allo -isoleucine stereochemistry
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A simple 1H and 13C NMR spectrometric analysis is demonstrated that permits differentiation of isoleucine and allo-isoleucine residues by inspection of the chemical shift and coupling constants of the signals associated with the proton and carbon at the α-stereocentre. This is applied to the estimation of epimerisation during metal-free N-arylation and peptide coupling reactions.
- Anderson, Zoe J.,Hobson, Christian,Needley, Rebecca,Song, Lijiang,Perryman, Michael S.,Kerby, Paul,Fox, David J.
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supporting information
p. 9372 - 9378
(2017/11/22)
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- Synthesis of novel ethyl 1-ethyl-6-fluoro-7-(fatty amido)-1,4-dihydro-4-oxoquinoline-3-carboxylate derivatives and their biological evaluation
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A series of novel ethyl 1-ethyl-6-fluoro-7-(fatty amido)-1,4-dihydro-4-oxoquinoline-3-carboxylate derivatives were prepared through multistep synthesis. The key step in the synthesis was to obtain the C-7 fatty amide derivative. The azide was selectively formed at C-7 position using sodium azide at 60 °C. Subsequently, the azide was reduced under mild conditions using zinc and ammonium chloride to form the corresponding amine. The synthesized derivatives were further subjected to biological evaluation studies like cytotoxicity against a panel of cancer cell lines such as DU145, A549, SKOV3, MCF7 and normal lung cells, IMR-90 as well as with antimicrobial and antioxidant activities. It was observed that the carboxylated quinolone derivatives with hexanoic (8a), octanoic (8b), lauric (8d) and myristic (8e) moieties exhibited promising cytotoxicity against all the tested cancer cell lines. The results also suggested that hexanoic acid-based fatty amide carboxylated quinolone derivative (8a) exhibited promising activity against both bacterial and fungal strains and significant antibacterial activity was observed against Staphylococcus aureus MTCC 96 (MIC value of 3.9 μg/mL). The compound 8a also showed excellent anti-biofilm activity against Staphylococcus aureus MTCC 96 and Bacillus subtilis MTCC 121 with MIC values of 2.1 and 4.6 μg/mL, respectively.
- Venepally, Vijayendar,Prasad,Poornachandra,Kumar, C. Ganesh,Jala, Ram Chandra Reddy
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supporting information
p. 613 - 617
(2016/01/09)
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- Metal-Free Oxidation of Primary Amines to Nitriles through Coupled Catalytic Cycles
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Synergism among several intertwined catalytic cycles allows for selective, room temperature oxidation of primary amines to the corresponding nitriles in 85-98 % isolated yield. This metal-free, scalable, operationally simple method employs a catalytic quantity of 4-acetamido-TEMPO (ACT; TEMPO=2,2,6,6-tetramethylpiperidine N-oxide) radical and the inexpensive, environmentally benign triple salt oxone as the terminal oxidant under mild conditions. Simple filtration of the reaction mixture through silica gel affords pure nitrile products.
- Lambert, Kyle M.,Bobbitt, James M.,Eldirany, Sherif A.,Kissane, Liam E.,Sheridan, Rose K.,Stempel, Zachary D.,Sternberg, Francis H.,Bailey, William F.
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supporting information
p. 5156 - 5159
(2016/04/09)
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- A Multidimensional Diversity-Oriented Synthesis Strategy for Structurally Diverse and Complex Macrocycles
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Synthetic macrocycles are an attractive area in drug discovery. However, their use has been hindered by a lack of versatile platforms for the generation of structurally (and thus shape) diverse macrocycle libraries. Herein, we describe a new concept in library synthesis, termed multidimensional diversity-oriented synthesis, and its application towards macrocycles. This enabled the step-efficient generation of a library of 45 novel, structurally diverse, and highly-functionalized macrocycles based around a broad range of scaffolds and incorporating a wide variety of biologically relevant structural motifs. The synthesis strategy exploited the diverse reactivity of aza-ylides and imines, and featured eight different macrocyclization methods, two of which were novel. Computational analyses reveal a broad coverage of molecular shape space by the library and provides insight into how the various diversity-generating steps of the synthesis strategy impact on molecular shape.
- Nie, Feilin,Kunciw, Dominique L.,Wilcke, David,Stokes, Jamie E.,Galloway, Warren R. J. D.,Bartlett, Sean,Sore, Hannah F.,Spring, David R.
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supporting information
p. 11139 - 11143
(2016/10/13)
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- Preparation method of high-purity 12-methyltridecanal
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The invention relates to the field of fine chemical engineering, in particular to a preparation method of high-purity 12-methyltridecanal: 10-undecylenic acid is taken as a raw material, and is subjected to four-step reactions including amidation, Grignard reaction, hydrogenation reduction and alkenyl ozonation. The method has the advantages that the raw material is low in cost and easy to obtain, steps are few, reaction conditions are mild, the impurity content is low, the purification is easy, the reaction repeatability is high, the stability is high, and the method is suitable for industrial mass production.
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Paragraph 0014; 0015; 0016; 0017
(2017/07/22)
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- Synthesis of (R)-(-)-muscone from (R)-5-bromo-4-methylpentanoate: A chiron approach
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A synthesis of (R)-muscone (1), a valuable musk odorant, is presented. The stereogenic center of muscone was introduced from methyl (R)-5-bromo-4-methylpentanoate (5), a chiral pool molecule developed in our group, and the macrocyclic ring was prepared by ring-closing metathesis (RCM) reaction. Using methyl (R)-5-bromo-4-methylpentanoate, we have accomplished a synthesis of (R)-muscone, a natural macrocyclic musk, based on chiral pool strategy.
- Shen, Junwei,Shi, Yong,Tian, Weisheng
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p. 683 - 687
(2015/06/25)
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- Synthesis of the tetracyclic ABCD ring systems of madangamines D-F
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Synthesis of the tetracyclic cores of madangamines D-F was achieved, featuring a reductive radical process from an ethoxycarbonyldichloroacetamide to build the morphan nucleus, a Mitsunobu-type aminocyclization toward the common diazatricyclic intermediate, and ring-closing metathesis reactions for the macrocyclization step leading to the 13- to 15-membered rings.
- Diaba, Fa??za,Pujol-Grau, Climent,Mart??nez-Laporta, Agust??n,Fern??ndez, Israel,Bonjoch, Josep
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supporting information
p. 568 - 571
(2015/03/04)
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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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- Using the same method and termiteproof termiteproof agent
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PROBLEM TO BE SOLVED: To provide a termite-proofing agent exhibiting high termite-proofing effect and enabling its own production cost to be reduced, and to provide a termite-proofing method using the same. SOLUTION: The termite-proofing agent is provided, which includes an amide compound represented by general formula (1). In general formula (1), either one of X1and X2is a halogen atom, alkyl or (substituted) phenyl, the other being H; alternatively, the X1and X2are optionally bound to each other to form a (substituted) saturated or unsaturated 5- or 6-membered ring; Y is a 6-14C alkylene group; and Z is amido group including methyl, vinyl or two disubstituted groups. COPYRIGHT: (C)2012,JPOandINPIT
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Paragraph 0132
(2016/12/16)
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- Facile and efficient KOH-catalysed reduction of esters and tertiary amides
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Esters and tertiary amides were efficiently reduced to their corresponding alcohols and amines in high yields under mild and environmentally friendly conditions. The presented KOH-catalysed system involves a simple hydrosilylation procedure that is carried out under solvent-free conditions and does not require the use of inert conditions.
- Fernandez-Salas, Jose A.,Manzini, Simone,Nolan, Steven P.
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supporting information
p. 9758 - 9760
(2013/10/21)
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- Synthesis and biological evaluation of new flavonoid fatty acid esters with anti-adipogenic and enhancing glucose consumption activities
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Oleoyl Formononetin (OF) has good weight loss activity and hypolipidemic activity, could improve insulin sensitivity and suppress adipogenesis. To acquire better biological activities, three series of flavonoid fatty acid esters were designed and synthesized by optimizing the structure of OF. Their bioactivities were assayed in vitro. Some of these novel compounds could effectively inhibit preadipocyte proliferation and adipogenesis. Moreover, they could enhance glucose consumption in adipocytes notably.
- Zhao, Wei,Sun, Jie,Xiang, Hua,Zeng, Yan-Yan,Li, Xiao-Bo,Xiao, Hong,Chen, De-Ying,Ma, Ren-Ling
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experimental part
p. 3192 - 3203
(2011/06/24)
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- Copper-catalyzed C(sp3)-C(sp3) bond formation using a hypervalent iodine reagent: An efficient allylic trifluoromethylation
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An efficient copper-catalyzed allylic trifluoromethylation reaction has been developed. This reaction provides a general and straightforward way to synthesize allylic trifluoromethylated compounds under mild conditions.
- Wang, Xi,Ye, Yuxuan,Zhang, Songnan,Feng, Jiajie,Xu, Yan,Zhang, Yan,Wang, Jianbo
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supporting information; experimental part
p. 16410 - 16413
(2011/11/29)
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- 4, 4' disubstituted 4H-cyclopentadithiophene and new methods for synthesising the same
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The present invention relates to a method for the synthesis of a compound having the following general formula: the method comprising the step of reacting, in presence of a diprotic acid having a negative pKa, a compound having the general formula: wherein R1 and R2 are organic groups and wherein X and Y are independently selected from the group consisting of hydrogen, chloro, bromo, iodo, boronic acid, boronate esters, borane, pseudohalogen and organotin. It further relates to compounds so obtained and to compounds resulting from the ring closure of compound (II).
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Page/Page column 46-47
(2012/01/06)
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- Continuous photochemical generation of catalytically active [CpRu] + complexes from CpRu(η6-C6H6)PF6
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Inter- and intramolecular ene-yne coupling reactions catalyzed by a species generated in situ via photolysis of CpRu(η6-C6H 6)PF6;an inexpensive, readily available, and shelf-stable complex;have been demonstrated under conditions of continuous flow. Importantly, the catalyst can be recovered quantitatively at the end of the reaction. Various functional groups are tolerated by the reaction, which affords skipped diene products in high yields.
- Gutierrez, Alicia C.,Jamison, Timothy F.
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supporting information; experimental part
p. 6414 - 6417
(2012/02/04)
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- Valence tautomerism in titanium enolates: Catalytic radical haloalkylation and application in the total synthesis of neodysidenin
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(Chemical Equation Presented) A direct ruthenium-catalyzed radical chloroalkylation of N-acyl oxazolidinones capitalizing on valence tautomerism of titanium enolates has been developed. The chloroalkylation method served as the centerpiece in the enantioselective total synthesis of trichloroleucine-derived marine natural product neodysidenin.
- Beaumont, Stephane,Ilardi, Elizabeth A.,Monroe, Lucas R.,Zakarian, Armen
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supporting information; experimental part
p. 1482 - 1483
(2010/04/03)
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- Synthesis and biological evaluation of isoflavone fatty acid esters with potential weight loss and hypolipidemic activities
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A series of isoflavone fatty acid esters were designed on the basis of endogenous oleoyl-estrone using estrogen moiety modification strategy. Ten new compounds were synthesized, and their body weight loss and hypolipidemic bioactivities were assayed. Some of these novel compounds could effectively inhibit the differentiation of 3T3-L1 preadipocytes in vitro. The most potent compound 1a significantly decreased the body weight and white adipose tissue weight in a high-fat diet-induced rat model. Also, compound 1a showed good hypolipidemic activity and low toxicity.
- Xiang, Hua,Zhao, Wei,Xiao, Hong,Qian, Lei,Yao, Yao,Li, Xiao-Bo,Liao, Qing-Jiang
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experimental part
p. 3036 - 3042
(2010/07/06)
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- Synthesis and characterization of symmetrical banana shaped liquid crystalline polyethers
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A series of banana shaped allyl terminated liquid crystalline bis{[4′(10-undecenoyloxy)-1,1′biphenyl-4-carboxylate}s varied with H, COOCH3, Cl and NO2 substituents in the central phenyl ring were synthesized and characterized by FT-IR, 1H NMR and 13C NMR spectroscopy. Effect of substituents on the mesomorphic property was examined by polarized optical microscopy (POM) and exhibited B1 and nematic mesophases. Differential scanning calorimetry (DSC) measurements confirmed the LC property. Allyl group in the terminal position was epoxidized and polymerized to get banana shaped liquid crystalline ladder polyethers by ring opening polymerization and characterized spectroscopically. POM investigations displayed the development of enantiotropic grainy textures for polyethers and confirmed by DSC. Thermogravimetric analysis revealed that they were decomposed at high temperatures with good char yield.
- Balamurugan,Kannan
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experimental part
p. 44 - 52
(2010/02/15)
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- Convenient one-pot synthesis of novel 2-substituted benzimidazoles, tetrahydrobenzimidazoles and imidazoles and evaluation of their in vitro antibacterial and antifungal activities
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A series of novel 2-substituted benzimidazoles and imidazoles have been synthesized from long-chain alkenoic acids. The reactions occurred under relatively mild conditions and afforded the desired product in good yields. The structures of these compounds have been elucidated by elemental and spectral (IR, 1H NMR, 13C NMR, mass) analyses. Furthermore, compounds were screened for in vitro antibacterial activity against the representative panel of two Gram-positive and two Gram-negative bacteria. All the synthesized compounds were also tested for their inhibitory action against five strains of fungus. The various compounds show potent inhibitory action against test organisms.
- Sharma, Shweta,Gangal, Saloni,Rauf, Abdul
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experimental part
p. 1751 - 1757
(2009/05/30)
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- Long-chain 3-acyl-4-hydroxycoumarins: Structure and antibacterial activity
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By reacting 4-hydroxycoumarin with long-chain acyl chlorides, a number of new 3-acyl derivatives were prepared and the relationship was studied between their structures and activities against Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, and Propionibacterium acnes ATCC 11827. Antibacterial activity was associated with enolic tautomers of a tricarbonylmethane group bearing a lipophilic side chain (undec-10-enoyl, undec-10-ynoyl, palmitoyl or octadec-9-enoyl). A newly synthesized 2-acyl derivative of 2H-indene-1,3-dione containing the same tricarbonylmethane motif showed a comparable activity.
- Cravotto, Giancarlo,Tagliapietra, Silvia,Cappello, Rossella,Palmisano, Giovanni,Curini, Massimo,Boccalini, Marco
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p. 129 - 132
(2007/10/03)
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- Halogen-modified silicon, surfaces
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Chemically-modified surfaces on unoxidized, bromine- or iodine-terminated carbon, silicon, and germanium substrates are disclosed. Visible light mediates the reaction of protected ω-modified, α-unsaturated aminoalkenes (preferred) with bromine- or iodine-terminated carbon, silicon, or germanium surfaces. Removal of the protecting group yields an aminoalkane-modified silicon surface. These amino groups can be coupled to terminal-modified oligonucleotides using a bifunctional crosslinker, thereby permitting the preparation of modified surfaces and arrays. Methods for controlling the surface density of molecules attached to the substrate are also disclosed.
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- Liquid-crystalline elastomers containing sulfonic acid groups
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A series of ionic liquid-crystalline (LC) elastomers were synthesized by using chemical cross-linking agents containing sulfonic acid groups, which were siloxane-based materials. A ionic divinyl monomer 2,2′-(1,2-ethenediyl)bis[5-[(4-undecenoyloxy)phenyl]azo]benzenesulfonic acid was used as chemical cross-linking agent. Cholest-5-en-3-ol(3β)-10-undecenoate was synthesized as a liquid-crystalline monomer. The effective cross-link density of the ionic elastomers was determined by swelling experiments in organic/buffer mixtures. Their liquid-crystalline properties were characterized by DSC, POM, and SAXS. A proposed multilayer buildup containing LC segment structure and ionic cross-linking lamellar structure separated by siloxane chains was given. The ion aggregated in domains forces the siloxane chains to fold and form an irregular lamellar structure. The ionic cluster lamellae may be tangled with the rigid mesogenic groups of LC segments to form multiple blocks. Liquid-crystal mesophase region of the polymers become narrow with increasing ionic cross-linking content.
- Zhang, Bao-Yan,Meng, Fan-Bao,Zang, Bao-Ling,Hu, Jian-She
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p. 3320 - 3326
(2007/10/03)
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- Modified carbon, silicon, and germanium surfaces
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Chemically-modified surfaces on unoxidized carbon, silicon, and germanium substrates are disclosed. Ultraviolet radiation mediates the reaction of protected ω-modified, α-unsaturated aminoalkenes (preferred) with hydrogen-terminated carbon, silicon, or germanium surfaces. Removal of the protecting group yields an aminoalkane-modified silicon surface. These amino groups can be coupled to terminal-modified oligonucleotides using a bifunctional crosslinker, thereby permitting the preparation of modified surfaces and arrays. Methods for controlling the surface density of molecules attached to the substrate are also disclosed.
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- Callipeltoside A: Total synthesis, assignment of the absolute and relative configuration, and evaluation of synthetic analogues
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The total synthesis of the novel antitumor agent callipeltoside A, as well as several analogues, is accomplished and allows assignment of the stereochemistry not previously established. A convergent strategy is employed wherein the target is dissected into three units - the core macrolactone, the sugar callipeltose, and a cyclopropyl bearing chain. The strategy for the synthesis of the macrolactone derives from employment of diastereoselective aldol reactions that emanate from an 11 carbon piece. The stereochemistry of the latter derives from the chiral pool and two asymmetric reactions - a ketone reduction using CBS-oxazaborolidine and a Pd catalyzed asymmetric allylic alkylation (AAA). The novelty of the latter protocol is its control of regioselectivity as well as absolute configuration. The trisubstituted olefin is generated using an alkene-alkyne coupling to create a trisubustituted olefin with complete control of geometry. The excellent chemo- and regioselectivity highlights the synthetic potential of this new ruthenium catalyzed process. The macrolactonization employs in situ formation of an acylketene generated by the thermolysis of a m-dioxolenone. Two strategies evolved for attachment of the side chain-one based upon olefination and a second upon olefin metathesis. The higher efficiency of the latter makes it the method of choice. A novel one pot olefin metathesis-Takai olefination protocol that should be broadly applicable is developed. The sugar is attached by a glycosylation by employing the O-trichloroacetimidate. This route provided both C-13 epimers of the macrolactone by using either enantiomeric ligand in the Pd AAA reaction. It also provided both trans-chlorocyclopropane diastereomers of callipeltoside A which allows the C-20 and C-21 configuration to be established as S and R, respectively. The convergent nature of the synthesis in which the largest piece, the macrolatone, require only 16 linear steps imparts utility to this strategy for the establishment of the structure-activity relationship. Initial biological testing demonstrates the irrelevance of the chloro substituent and the necessity of the sugar.
- Trost, Barry M.,Gunzner, Janet L.,Dirat, Olivier,Rhee, Young H.
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p. 10396 - 10415
(2007/10/03)
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- Carbon-halogen bond activation by Nickel catalyst: Synthesis of alkenes, from 1,2-dihalides
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Unsaturated hydrocarbons can easily be prepared in a few seconds starting from 1,2 dibromides in the presence of a catalytic amount of Nickel diphenylphosphinoethane dichloride (NidppeCl2) and tri.n.butyl tin hydride, (TBTH) at room temperature. The dependencie of the nature of starting dihalides is investigated.
- Malanga, Corrado,Mannucci, Serena,Lardicci, Luciano
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p. 1021 - 1028
(2007/10/03)
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- On the synthesis of vinyl isonitriles
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A reversal of the stereochemistry of base mediated isomerisation of some isonitrile epoxides to hydroxy-vinyl isonitriles on changing from lithium diisopropylamide to lithium bis(trimethylsilyl)amide is reported and applied to a synthesis of racemic desepoxyaerocyanidin.
- Baldwin, Jack E.,Chen, Deqi,Russell, Andrew T.
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p. 2389 - 2390
(2007/10/03)
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- Polyanion inhibitors of human immunodeficiency virus and other viruses. Part 2. Polymerized anionic surfactants derived from amino acids and dipeptides
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A series of new polyanions was synthesized via γ-polymerization, in aqueous micellar solution, of ω-unsaturated anionic surfactants whose polar head was derived from amino acids or dipeptides. The obtained polyanions were evaluated for their activity against human immunodeficiency virus (HIV-1, HIV-2) and various other RNA and DNA viruses. All the test compounds proved active against HIV-1 and HIV-2, their 50% inhibitory concentration (IC50) being in the range of 0.04-7.5 μg/mL, while they were not toxic to the host cells (CEM-4 or MT-4) at concentrations up to 100 μg/mL or higher. The HIV- inhibitory effect increased with the hydrophilic character of the amino acid moiety. The compounds were found to interact with both the viral envelope glycoprotein gp120 and the cellular CD4 receptor, thus blocking virus-cell binding and virus-induced syncytium formation. These polyanions also proved active against human cytomegalovirus at about the same IC50 as for HIV. In addition, they were also active, albeit at somewhat higher IC50 values (0.8-20 μg/mL), against other enveloped viruses such as respiratory syncytial virus and arenaviruses (Junin and Tacaribe). At yet higher IC50 values (≥20 μg/mL), some of the compounds showed activity against influenza A virus. No activity was observed with any of the compounds against vesicular stomatitis virus, Sindbis virus, Semliki forest virus, influenza B, parainfluenza type 3, and the nonenveloped viruses Coxsackie type B4, polio type 1, and reovirus type 1.
- Leydet,El Hachemi,Boyer,Lamaty,Roque,Schols,Snoeck,Andrei,Ikeda,Neyts,Reymen,Este,Witvrouw,De Clercq
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p. 1626 - 1634
(2007/10/03)
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- Direct Ni° mediated synthesis of ketones from acyl bromides and Grignard reagents
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A catalytic amount of NidppeCl2 converts an acyl bromide directly into ketones at 0°C in THF in the presence of a Grignard reagent. The described procedure represents a useful way to afford dialkyl, diaryl or alkyl aryl ketones as well as 1,2-diketones. In the adopted reaction conditions double bonds, esters and ketones are unaffected.
- Malanga, Corrado,Aronica, Laura A.,Lardicci, Luciano
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p. 9185 - 9188
(2007/10/02)
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- Vanilloids. 1. Analogs of Capsaicin with Antinociceptive and Antiinflammatory Activity
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As part of a program to establish structure-activity relationships for vanilloids, analogs of the pungent principle capsaicin, the alkyl chain portion the parent structure (and related compounds derived from homovanillic acid) was varied.In antinociceptive and antiinflammatory assays (rat and mouse hot plate and croton oil-inflamed mouse ear), compounds with widely varying alkyl chain structures were active.Short-chain compounds were active by systemic administration in the assays mentioned above but they retained the high pungency and acute toxicity characteristic of capsaicin.In contrast, the long chain cis-unsaturates, NE-19550 (vanillyloleamide) and NE-28345 (oleylhomovanillamide), were orally active, less pungent, and less acutely toxic than capsaicin.The potential of these compounds as antiinflammatory/analgesic agents is discussed in light of recent data on the mechanism of action of vanilloids on sensory nerve fibers.
- Janusz, John M.,Buckwalter, Brian L.,Young, Patricia A.,LaHann, Thomas R.,Farmer, Ralph W.,et al.
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p. 2595 - 2604
(2007/10/02)
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- Supramolecular asymmetric induction with a NADH model reagent grafted on silica
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A model of NADH issued from a thieno dihydropyridine derivative has been grafted onto a silica matrix bearing on another part a chiral auxiliary.Two strategies were implemented to obtain the corresponding reagents.In the first case, the reagent and the auxiliary were grafted to the silica by means of two different arms.In the second case, the reagent and the auxiliary were linked to two arms which are brought together before beiing linked to the silica matrix.The reagents thus obtained were involved in the reduction of methyl phenyl glyoxylate and enantiomeric excesses of 20 and 35percent were obtained.Key words: NADH models / grafting on silica / supramolecular induction
- Losset, D.,Dupas, G.,Duflos, J.,Bourguignon, J.,Queguiner, G.
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p. 721 - 729
(2007/10/02)
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