- New gold (I) complexes with 5-aromatic ring-1, 3, 4-oxadiazole-2-thione and triphenylphosphine as potential multifunctional materials
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Three new gold (I) complexes (4a, 4b, 4c) with 5-aromatic ring-1, 3, 4-oxadiazole-2-thione and triphenylphosphine as ligands were synthesized. Structures of 4a and 4b were determined through X-ray single-crystal diffraction, and it displayed that 4a and 4b had the same metal coordination pattern, wherein the ligand was coordinated by the sulfur atom to the central metal ion of gold (I). The optical properties of these gold (I) complexes were studied both in solution and in solid-state. In DMSO, 4a and 4b peaked at 415 nm and 443 nm, respectively, and the CIE coordinates of 4a and 4b in the solid-state were in the green area namely, (0.26, 0.46) and (0.24, 0.41). HOMO/LUMO levels and bandgaps of 4a, 4b and 4c were assessed by UV spectrum estimation, electrochemical method, and theoretical calculations. The observation hinted that the photophysical properties and energy levels of these gold (I) complexes can be adjusted by the introduction of different substituent aromatic rings at the 5-position of the 1, 3, 4-oxadiazole-2-thiol moiety. The findings of good optical, electrochemical and thermal properties of these new gold (I) complexes demonstrated their potential in the future studies as multifunctional materials.
- Zhao, Yu Qiang,Zhou, Jie,He, Renze,Wang, Guang Ke,Miao, Lan Xi,Xie, Xiao Guang,Zhou, Ying
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supporting information
(2020/12/02)
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- 4-Amino-1,2,4-triazole-3-thione-derived Schiff bases as metallo-β-lactamase inhibitors
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Resistance to β-lactam antibiotics in Gram-negatives producing metallo-β-lactamases (MBLs) represents a major medical threat and there is an extremely urgent need to develop clinically useful inhibitors. We previously reported the original binding mode of 5-substituted-4-amino/H-1,2,4-triazole-3-thione compounds in the catalytic site of an MBL. Moreover, we showed that, although moderately potent, they represented a promising basis for the development of broad-spectrum MBL inhibitors. Here, we synthesized and characterized a large number of 4-amino-1,2,4-triazole-3-thione-derived Schiff bases. Compared to the previous series, the presence of an aryl moiety at position 4 afforded an average 10-fold increase in potency. Among 90 synthetic compounds, more than half inhibited at least one of the six tested MBLs (L1, VIM-4, VIM-2, NDM-1, IMP-1, CphA) with Ki values in the μM to sub-μM range. Several were broad-spectrum inhibitors, also inhibiting the most clinically relevant VIM-2 and NDM-1. Active compounds generally contained halogenated, bicyclic aryl or phenolic moieties at position 5, and one substituent among o-benzoic, 2,4-dihydroxyphenyl, p-benzyloxyphenyl or 3-(m-benzoyl)-phenyl at position 4. The crystallographic structure of VIM-2 in complex with an inhibitor showed the expected binding between the triazole-thione moiety and the dinuclear centre and also revealed a network of interactions involving Phe61, Tyr67, Trp87 and the conserved Asn233. Microbiological analysis suggested that the potentiation activity of the compounds was limited by poor outer membrane penetration or efflux. This was supported by the ability of one compound to restore the susceptibility of an NDM-1-producing E. coli clinical strain toward several β-lactams in the presence only of a sub-inhibitory concentration of colistin, a permeabilizing agent. Finally, some compounds were tested against the structurally similar di-zinc human glyoxalase II and found weaker inhibitors of the latter enzyme, thus showing a promising selectivity towards MBLs.
- Baud, Damien,Bebrone, Carine,Becker, Katja,Benvenuti, Manuela,Cerboni, Giulia,Chelini, Giulia,Cutolo, Giuliano,De Luca, Filomena,Docquier, Jean-Denis,Feller, Georges,Fischer, Marina,Galleni, Moreno,Gavara, Laurent,Gresh, Nohad,Kwapien, Karolina,Legru, Alice,Mangani, Stefano,Mercuri, Paola,Pozzi, Cecilia,Sannio, Filomena,Sevaille, Laurent,Tanfoni, Silvia,Verdirosa, Federica,Berthomieu, Dorothée,Bestgen, Beno?t,Frère, Jean-Marie,Hernandez, Jean-Fran?ois
-
supporting information
(2020/09/16)
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- Porous organic cage stabilised palladium nanoparticles: Efficient heterogeneous catalysts for carbonylation reaction of aryl halides
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Porous organic cage stabilised palladium nanoparticles were successfully prepared using methanol as a mild reductant. The as-prepared porous composite materials show high catalytic activity for the carbonylation reaction of aryl halides under mild conditions.
- Zhang, Yong,Xiong, Yu,Ge, Jin,Lin, Rui,Chen, Chen,Peng, Qing,Wang, Dingsheng,Li, Yadong
-
supporting information
p. 2796 - 2799
(2018/03/21)
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- 1,2,4-Triazole-3-thione Compounds as Inhibitors of Dizinc Metallo-β-lactamases
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Metallo-β-lactamases (MBLs) cause resistance of Gram-negative bacteria to β-lactam antibiotics and are of serious concern, because they can inactivate the last-resort carbapenems and because MBL inhibitors of clinical value are still lacking. We previously identified the original binding mode of 4-amino-2,4-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione (compound IIIA) within the dizinc active site of the L1 MBL. Herein we present the crystallographic structure of a complex of L1 with the corresponding non-amino compound IIIB (1,2-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione). Unexpectedly, the binding mode of IIIB was similar but reverse to that of IIIA. The 3 D structures suggested that the triazole–thione scaffold was suitable to bind to the catalytic site of dizinc metalloenzymes. On the basis of these results, we synthesized 54 analogues of IIIA or IIIB. Nineteen showed IC50 values in the micromolar range toward at least one of five representative MBLs (i.e., L1, VIM-4, VIM-2, NDM-1, and IMP-1). Five of these exhibited a significant inhibition of at least four enzymes, including NDM-1, VIM-2, and IMP-1. Active compounds mainly featured either halogen or bulky bicyclic aryl substituents. Finally, some compounds were also tested on several microbial dinuclear zinc-dependent hydrolases belonging to the MBL-fold superfamily (i.e., endonucleases and glyoxalase II) to explore their activity toward structurally similar but functionally distinct enzymes. Whereas the bacterial tRNases were not inhibited, the best IC50 values toward plasmodial glyoxalase II were in the 10 μm range.
- Sevaille, Laurent,Gavara, Laurent,Bebrone, Carine,De Luca, Filomena,Nauton, Lionel,Achard, Maud,Mercuri, Paola,Tanfoni, Silvia,Borgianni, Luisa,Guyon, Carole,Lonjon, Pauline,Turan-Zitouni, Gülhan,Dzieciolowski, Julia,Becker, Katja,Bénard, Lionel,Condon, Ciaran,Maillard, Ludovic,Martinez, Jean,Frère, Jean-Marie,Dideberg, Otto,Galleni, Moreno,Docquier, Jean-Denis,Hernandez, Jean-Fran?ois
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p. 972 - 985
(2017/06/27)
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- Method of converting amide and urea into ester
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The invention provides a method of converting amide and urea into ester. In the method, different types of amide and urea are used as substrate, alcohol or phenol is used as nucleophile, iron salt is used as catalyst, and acid is used as additive, the conversion of amide and urea into ester is achieved under a mild condition. The method is characterized in that cheap iron salt is used as the catalyst, the commercialized amide, urea, and alcohol are used as the substrate, and the conversion of amide to ester is achieved in one step. The method has the advantages that the reaction condition is mild, the raw materials are cheap and easy to obtain, the reaction substrate is wide in adaptability, the selectivity and yield of the product are very high, the product is green and environmentally friendly and the like, and the method has good prospects for industrial applications.
- -
-
Paragraph 0057-0059
(2017/08/30)
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- SO2F2-Mediated One-Pot Synthesis of Aryl Carboxylic Acids and Esters from Phenols through a Pd-Catalyzed Insertion of Carbon Monoxide
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A one-pot Pd-catalyzed carbonylation of phenols into their corresponding aryl carboxylic acids and esters through the insertion of carbon monoxide has been developed. This procedure offers a direct synthesis of aryl carboxylic acids and esters from inexpensive and abundant starting materials (phenols, SO2F2 and CO) under mild conditions. This method tolerates a broad range of functional groups and is also applicable for the modification of complicated natural products.
- Fang, Wan-Yin,Leng, Jing,Qin, Hua-Li
-
supporting information
p. 2323 - 2331
(2017/09/06)
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- Practical: In situ -generation of phosphinite ligands for palladium-catalyzed carbonylation of (hetero)aryl bromides forming esters
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An effective method for alkoxycarbonylation of (hetero)aryl bromides is developed in the presence of in situ-generated phosphinite ligands tBu2POR (R = nBu, nPr, Et or Me). For this purpose commercially available tBu2PCl was used as the pre-ligand in the presence of different alcohols. For the first time cross coupling reactions with two alcohols-one generating the ligand, the other used as substrate-were developed. Through this method, ligand optimization can be performed in a more efficient manner and the desired products could be obtained with good yields and selectivity.
- Wang, Lin,Neumann, Helfried,Spannenberg, Anke,Beller, Matthias
-
supporting information
p. 7469 - 7472
(2017/07/12)
-
- Synthesis of naphthalenecarboxylic and naphthalenedicarboxylic acids from naphthalene, carbon tetrachloride, and alcohols in the presence of iron catalysts
-
Alkyl naphthalenecarboxylates and dialkyl naphthalenedicarboxylates have been synthesized by reactions of naphthalene and its derivatives with alcohols and carbon tetrachloride in the presence of iron catalysts.
- Baiguzina,Erokhina,Khusnutdinov
-
p. 389 - 395
(2017/05/01)
-
- Room Temperature Carbonylation of (Hetero) Aryl Pentafluorobenzenesulfonates and Triflates using Palladium-Cobalt Bimetallic Catalyst: Dual Role of Cobalt Carbonyl
-
An efficient method for the carbonylation of (hetero) aryl pentafluorobenzenesulfonates and triflates under exceptionally mild conditions using palladium/dicobalt octacarbonyl [Pd/Co2(CO)8] has been developed. Besides acting as carbon monoxide (CO) source, Co2(CO)8enhances the reaction rate by accelerating the CO insertion through an in situ generated bimetallic palladium cobalt tetracarbonyl [Pd-Co(CO)4] complex. Under the optimized reaction condition, carbonylation of a wide range of activated and deactivated, as well as sterically hindered and heteroaromatic, substrates proceeded efficiently at room temperature. The high chemoselectivity and improved synthesis of biologically relevant Isoguvacine and Lazabemide intermediates highlights its scope as a valuable synthetic method. The generality of this protocol was further extended to other electrophiles (bromides, chlorides and tosylates). (Figure presented.).
- Joseph, Jayan T.,Sajith, Ayyiliath M.,Ningegowda, Revanna C.,Shashikanth, Sheena
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p. 419 - 425
(2017/02/10)
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- Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides
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We report a palladium-catalyzed method to synthesize acid chlorides by the chlorocarbonylation of aryl bromides. Mechanistic studies suggest the combination of sterically encumbered PtBu3 and CO coordination to palladium can rapidly equilibrate the oxidative addition/reductive elimination of carbon-halogen bonds. This provides a useful method to assemble highly reactive acid chlorides from stable and available reagents, and can be coupled with subsequent nucleophilic reactions to generate new classes of carbonylated products. The Good, the Bad and the Bulky! By employing a sterically encumbered phosphine ligand, tri-tert-butyl phosphine, under palladium catalysis inert aryl bromides are chlorocarbonylated to create reactive acid chlorides by reversible carbon-halogen bond reductive elimination. This general platform allows for an expanded scope of the Heck carbonylation reaction to include previously incompatible nucleophiles.
- Quesnel, Jeffrey S.,Kayser, Laure V.,Fabrikant, Alexander,Arndtsen, Bruce A.
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supporting information
p. 9550 - 9555
(2015/06/30)
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- Palladium-Catalyzed Carbonylations of Arylboronic Acids: Synthesis of Arylcarboxylic Acid Ethyl Esters
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An approach for the palladium-catalyzed ethoxycarbonylations of arylboronic acids using diethyl pyrocarbonate as carbon monoxide/carbon dioxide (CO/CO2) surrogate in moderate to good yields has been investigated.
- Liang, Apeng,Han, Shuaijun,Wang, Liang,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
-
supporting information
p. 3104 - 3108
(2015/11/03)
-
- Metal-free aerobic oxidative esterification of aldehydes in the presence of cyanide
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A metal-free aerobic oxidative esterification of aldehydes in the presence of cyanide is described. Various aromatic aldehydes and sterically congested alcohols were amenable to this protocol. In addition, this method could be extended to the preparation of thioesters with a thiol in place of an alcohol. Furthermore, the cyanide-mediated aerobic oxidation of aldehydes was applied to the synthesis of lactones via intramolecular esterification in the absence of an alcohol.
- Kim, Yoo-Jin,Cheon, Cheol-Hong
-
supporting information
p. 2055 - 2061
(2015/08/18)
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- Oxidative esterification of alcohols and aldehydes using supported iron oxide nanoparticle catalysts
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The synthesis of esters has become an important industrial methodology over the past years because of the role that they serve in the chemical industry. In this study, we present the use of a novel catalyst for the direct conversion of aldehydes into esters. The yields obtained using supported iron oxide nanoparticle catalysts (FeNP) are very high (>90%). The catalyst is also shown to be very stable as shown by the recyclability study (up to 11 times).
- Rajabi, Fatemeh,Arancon, Rick A.D.,Luque, Rafael
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p. 101 - 103
(2015/02/19)
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- Novel arylhydrazone derivatives bearing a rhodanine moiety: Synthesis and evaluation of their antibacterial activities
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A series of arylhydrazone derivatives bearing a rhodanine moiety have been synthesized, characterized, and evaluated as antibacterial agents. Some of these compounds showed potent antibacterial activities against several different strains of Gram-positive bacteria, including multidrug-resistant clinical isolates. Of the compounds tested, IIk and IIIk were identified as the most effective, with minimum inhibitory concentration values of 2-4 μg/mL against multidrug-resistant Gram-positive organisms, including methicillin-resistant and quinolone-resistant Staphylococcus aureus. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 μg/mL.
- Li, Wei,Zheng, Chang-Ji,Sun, Liang-Peng,Song, Ming-Xia,Wu, Yan,Li, Yin-Jing,Liu, Yi,Piao, Hu-Ri
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p. 852 - 861
(2014/08/05)
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- Polymer supported Pd catalyzed carbonylation of aryl bromides for the synthesis of aryl esters and amides
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A polymer-anchored palladium(ii) catalyst was synthesized and characterized using various spectroscopic techniques. Its catalytic activity was evaluated for the alkoxycarbonylation and aminocarbonylation reactions. These carbonylation reactions were carried out for various substituted aryl bromides using alcohols and amines. Both the reactions were optimized by varying the bases, temperature and solvents. These experiments were carried out under high CO pressure. The catalyst was very stable and can be facilely recovered and reused six times without a significant decrease in its activity and selectivity. the Partner Organisations 2014.
- Islam, Sk Manirul,Ghosh, Kajari,Roy, Anupam Singha,Molla, Rostam Ali
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p. 38986 - 38999
(2014/11/07)
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- Highly selective trifluoroacetic ester/ketone metathesis: An efficient approach to trifluoromethyl ketones and esters
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A highly selective and atom efficient 'trifluoroacetic ester/ketone metathesis' has been sincerely witnessed. Enolizable alkyl (at least two non-hydrogen atoms) aryl ketones were found to react readily with ethyl trifluoroacetate under the promotion of NaH to afford trifluoroacetic ester/ketone exchange products, trifluoromethyl ketones (TFMKs), and aromatic acid esters, which were quite different from the general Claisen condensation products, 1,3-diketones. The outcome of the reaction between ketone and ethyl trifluoroacetate is strongly related to the structures of substrates, the steric congestion caused by alkyl group is in favor of the C-C bond cleavage. DFT investigation further disclosed that the metathesis reaction was a kinetically favored pathway. Using only a slight excess of cheap trifluoromethylation reagent, simple operation and mild conditions make it a practical method for preparation of TFMKs on large scale, as well as a new choice of converting aryl alkyl ketones to aromatic acid esters.
- Zhou, Yuhan,Yang, Dongmei,Luo, Gen,Zhao, Yilong,Luo, Yi,Xue, Na,Qu, Jingping
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p. 4668 - 4674
(2014/06/23)
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- An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters
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The Pd-catalyzed cross-coupling ethoxycarbonylation of aryl boronic acids with N-aryl-α-iminoesters affords aryl carboxylic esters via carbonyl-imino σ bond cleavage. This unprecedented mode of reaction allows regioselective installation of the ethoxycarbonyl group into target molecules. Mechanism studies have revealed that an unusual 1,2-aryl shift process is involved in the transformation. The Royal Society of Chemistry.
- Qian, Cheng,Chen, Jiayan,Fu, Meiqin,Zhu, Shiya,Chen, Wen-Hua,Jiang, Huanfeng,Zeng, Wei
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p. 6013 - 6022
(2013/09/12)
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- One-pot transformation of carboxylic acids into nitriles
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A variety of aromatic and aliphatic carboxylic acids were smoothly converted into the corresponding nitriles in good yields in a one-pot procedure by treatment with ethyl iodide/K2CO3/18-crown-6, followed by sodium diisobutyl-tert-butoxyaluminium hydride (SDBBA-H), and finally treatment with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH), and aqueous ammonia. This method is useful for the conversion of various aromatic and aliphatic carboxylic acids into the corresponding nitriles in a one-pot procedure. A variety of aromatic and aliphatic carboxylic acids were smoothly converted into the corresponding nitriles in good yields in a one-pot procedure by treatment with ethyl iodide/K2CO3/18-crown-6, followed by sodium diisobutyl-tert-butoxyaluminium hydride (SDBBA-H), and finally treatment with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH), and aqueous ammonia. Copyright
- Miyagi, Kotaro,Moriyama, Katsuhiko,Togo, Hideo
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p. 5886 - 5892
(2013/09/23)
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- Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents
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A series of novel 1,3,4-oxadiazole thioether derivatives (compounds 9-44) were designed and synthesized as potential inhibitors of thymidylate synthase (TS) and as anticancer agents. The in vitro anticancer activities of these compounds were evaluated against three cancer cell lines by the MTT method. Among all the designed compounds, compound 18 bearing a nitro substituent exhibited more potent in vitro anticancer activities with IC50 values of 0.7 ± 0.2, 30.0 ± 1.2, 18.3 ± 1.4 μM, respectively, which was superior to the positive control. In the further study, it was identified as the most potent inhibitor against two kinds of TS protein (for human TS and Escherichia coli TS, IC50 values: 0.62 and 0.47 μM, respectively) in the TS inhibition assay in vitro and the most potent antibacterial agents with MIC (minimum inhibitory concentrations) of 1.56-3.13 μg/mL against the tested four bacterial strains. Molecular docking and 3D-QSAR study supported that compound 18 can be selected as dual antitumor/antibacterial candidate in the future study.
- Du, Qian-Ru,Li, Dong-Dong,Pi, Ya-Zhou,Li, Jing-Ran,Sun, Jian,Fang, Fei,Zhong, Wei-Qing,Gong, Hai-Bin,Zhu, Hai-Liang
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p. 2286 - 2297
(2013/05/09)
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- Pd-catalyzed aldehyde to ester conversion: A hydrogen transfer approach
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Aliphatic and aromatic aldehydes are successfully converted into their corresponding esters using Pd(OAc)2 and XPhos. This approach utilizes a hydrogen transfer protocol: concomitant reduction of acetone to isopropanol provides an inexpensive and sustainable approach that mitigates the need for other oxidants.
- Tschaen, Brittany A.,Schmink, Jason R.,Molander, Gary A.
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supporting information
p. 500 - 503
(2013/04/11)
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- Ligand free palladium catalyzed decarboxylative cross-coupling of aryl halides with oxalate monoester salts
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Ligand free Pd-catalyzed decarboxylative cross-coupling of potassium oxalate monoester and derivatives with aryl iodides and bromides is described. Functionalized aromatic esters can be efficiently synthesized via this method with only 1.0 mol % Pd(OAc)2 catalyst without any phosphine ligand. This method illustrates an inexpensive and operationally simple method for the preparation of aromatic esters and acids, which is especially beneficial for a large scale synthesis.
- Li, Yan,Chen, Huan-Huan,Wang, Chu-Fei,Xu, Xiao-Lan,Feng, Yi-Si
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p. 5796 - 5799
(2012/10/29)
-
- ALLOSTERIC BINDING COMPOUNDS
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The present invention relates to allosteric binding compounds of formula (I), especially for the treatment of CNS disorders, together with pharmaceutical compositions and methods of treatment including these compounds.
- -
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Page/Page column 18
(2012/04/23)
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- Phosphonium chloride as a non-volatile chlorinating reagent: Preparation and reaction in no solvent or ionic liquid
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Reaction of triphenylphosphine with trichloroisocyanuric acid in no solvent or an ionic liquid gave the corresponding phosphonium chloride, which can be used as a cheap and safe chlorinating reagent. Conversion of hydroxyheterocycles to chloroheterocycles, carboxylic acids to carboxylic acid chlorides, and primary amides to nitriles were accomplished by using the phosphonium chloride in excellent to good yields.
- Sugimoto, Osamu,Harada, Yukihiro,Tanji, Ken-Ichi
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p. 1583 - 1590
(2013/08/15)
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- Synthesis using microwave irradiation, characterisation and antibacterial activity of Novel deoxycholic acid-triazole conjugates
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Novel deoxycholic acid 3α-triazole conjugates based on methyl 3α-chloroacetoxy-12α-hydroxy-cholanate have been synthesised. The synthesis is accelerated by microwave irradiation under solvent free conditions in the presence of K2CO3. Some of these compounds were tested for antibacterial activity against B.subtilis, P.aeruginosa and S.aureus. The preliminary results indicated that these deoxycholic acid-triazole conjugates have good inhibitory effect against B.subtilis. All of the compounds were characterised by 1H NMR, IR, ESI-MS spectra and elemental analyses.
- Yang, Jie,Zhao, Zhigang,Li, Hui
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scheme or table
p. 383 - 386
(2012/10/08)
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- Facile preparation of aromatic esters from aromatic bromides with ethyl formate or DMF and molecular iodine via aryllithium
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Various aromatic bromides were treated with n-BuLi and subsequently with ethyl formate, followed by the reaction with ethanol and molecular iodine in the presence of K2CO3 to provide the corresponding aromatic ethyl esters in good yields. Moreover, aromatic bromides could be transformed into the corresponding aromatic methyl esters in good yields by the treatment with n-BuLi and subsequently with DMF, followed by the reaction with methanol, molecular iodine, and K2CO3. Some aromatics could be also converted into the corresponding aromatic esters in good yields by the treatment with n-BuLi, and subsequently with ethyl formate or DMF, followed by the reaction with molecular iodine and K2CO3. The present reactions offer a novel route for the transition-metal-free, carbon-monoxide-free, and therefore environmentally benign one-pot conversion of aromatic bromides and aromatics into aromatic esters.
- Ushijima, Sousuke,Moriyama, Katsuhiko,Togo, Hideo
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experimental part
p. 4701 - 4709
(2012/07/28)
-
- Synthesis of new Schiff bases derived from dimers of 4-amino-3-(1-naphthyl) -5-thiomethyl-1, 2, 4-triazole using microwave irradiation
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An efficient method for the synthesis of novel Schiff bases derived from dimers of 4-amino-3-(1-naphthyl)-5-thiomethyl-1, 2, 4-triazole using microwave irradiation has been developed. Its distinct advantages are short reaction times, good conversions and eco-friendly to methodology. The structures of these new Schiff bases were established by1H NMR, IR, MS spectra and elemental analysis.
- Shi, Yun,Peng, Yongle,Zhao, Zhigang,Li, Guohua,Li, Huarong
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scheme or table
p. 15 - 17
(2011/04/26)
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- Synthesis of novel arylhydrazide molecular tweezer artificial receptors based on deoxycholic acid using microwave irradiation
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Eleven novel molecular tweezer anion receptors based on deoxycholic acid have been synthesised using microwave irradiation. Their structures were established by 1H NMR, IR, MS spectra and elemental analysis. Their binding properties were examined by UV-Vis spectra titration. The preliminary results indicate that these molecular tweezers show good recognition properties for H2PO4-, CH3COO- and NO3-.
- Li, Xiaorui,Zhao, Zhigang,Cheng, Yuyu,Li, Hui
-
experimental part
p. 234 - 237
(2011/07/08)
-
- Preparation of novel molecular tweezers based on 3,6-O-(2- acylhydrazinocarbonyl) esters of hyodeoxycholic acid using microwave irradiation
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Ten novel molecular tweezers based on the 3,6-O-(2-acylhydrazinocarbonyl) esters of hyodeoxycholic acid have been synthesised using microwave irradiation. Their structures were established by 1H NMR, IR, MS spectra and elemental analysis. Their binding properties were examined by UV-Vis spectra titration. The preliminary results indicate that these molecular tweezers show good recognition properties for Cl-, Br-, I-.
- Li, Xiaorui,Qiu, Liying,Mei, Qinggang,Bi, Qingwei,Zhao, Zhigang
-
scheme or table
p. 364 - 367
(2011/10/05)
-
- ALLOSTERIC BINDING COMPOUNDS
-
The present invention relates to allosteric binding compounds of formula (I), especially for the treatment of CNS disorders, together with pharmaceutical compositions and methods of treatment including these compounds.
- -
-
Page/Page column 54
(2010/09/17)
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- Design and synthesis of novel diphenic acid-based molecular tweezers
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The design and synthesis of a new type of molecular tweezers is reported which have a 2,2′-diphenic acid backbone and two side chains that are attached to the backbone. This type of molecular tweezers has been to incorporate multiple hydrogen bonding groups into cleft to provide both orientation and selective complexation of substrate.
- Li, Weijie,Wang, Xiaoqing,Zhao, Zhigang,Han, Tao
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experimental part
p. 106 - 108
(2010/06/19)
-
- Synthesis and structural characterisation of 2,4-bis(5-aryl-1,3,4-oxdiazol- 2-yl) pyridine derivatives
-
A convenient synthesis of 2,4-bis (5-aryl-1,3,4-oxdiazol-2-yl) derivatives of pyridine by the POCl3-mediated cyclodehydration of a variety of pyridine-2,4-dicarboxylic dihydrazides has been developed. The 20 novel intermediates and target molecules were characterised by IR, 1H NMR, MS and elemental analysis.
- Wang, Xiao Qing,Zhao, Zhi Gang,Liu, Xing Li,Li, Wei Jie
-
experimental part
p. 307 - 309
(2010/10/21)
-
- Design and synthesis of novel molecular tweezer anion receptors based on diphenic acid carbonyl thiosemicarbazide
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Ten novel molecular tweezer anion receptors based on diphenic acid carbonyl thiosemicarbazide have been designed and synthesised in high yield and their binding properties were examined by UV-Vis spectra titration. Their structures were characterised by 1H NMR, IR, MS spectra and elemental analysis.
- Li, Xiaorui,Zhao, Zhigang,Li, Guohua,Shi, Peiyu
-
experimental part
p. 410 - 413
(2010/12/19)
-
- Synthesis, biological evaluation, and molecular docking studies of 2-chloropyridine derivatives possessing 1,3,4-oxadiazole moiety as potential antitumor agents
-
A series of new 2-chloropyridine derivatives possessing 1,3,4-oxadiazole moiety were synthesized. Antiproliferative assay results indicated that compounds 6o and 6u exhibited the most potent activity against gastric cancer cell SGC-7901, which was more potent than the positive control. Especially, compound 6o exhibited significant telomerase inhibitory activity (IC 50 = 2.3 ± 0.07 μM), which was comparable to the positive control ethidium bromide. Docking simulation was performed to position compound 6o into the active site of telomerase (3DU6) to determine the probable binding model.
- Zheng, Qing-Zhong,Zhang, Xiao-Min,Xu, Ying,Cheng, Kui,Jiao, Qing-Cai,Zhu, Hai-Liang
-
scheme or table
p. 7836 - 7841
(2011/01/13)
-
- Synthesis of novel triazole derivatives of methyl 3-oxocholanate using microwave irradiation
-
An efficient rapid method for the synthesis of new triazole derivatives derived from methyl 3-oxocholanate under microwave irradiation has been developed. These new compounds were characterised by 1H NMR, IR, ESI-MS spectra and elemental analyses. Some of these triazoles were tested for antibacterial activity against Staphylococcus aureus, Candida albicans and Escherichia coli.
- Yang, Jie,Cheng, YuYu,Shi, ZhiChuan,Zhao, ZhiGang
-
experimental part
p. 680 - 683
(2011/04/26)
-
- Palladium-catalyzed aerobic oxidative carbonylation of arylboronate esters under mild conditions
-
(Figure Presented) "CO"n Air: The title reaction was carried out using [PdCl2(PPh3)2 ] as the catalyst precursor under very mild conditions (balloon pressure of CO and air, at 40- 50°C), and produced a wide range of aryl carboxyl esters 2 in good to excellent yields. Remarkable selectivity between oxidative carbonylation and homocoupling of arylboronate esters l was also achieved.
- Liu, Qiang,Li, Gang,He, Jun,Liu, Jing,Li, Peng,Lei, Aiwen
-
supporting information; experimental part
p. 3371 - 3374
(2010/07/06)
-
- Alkoxycarbonylation of aryl iodides catalyzed by Pd with a thiourea type ligand under balloon pressure of CO
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Palladium-catalyzed alkoxycarbonylation of aryl iodides with a thiourea-oxazoline type ligand has been achieved under mild conditions. Various functional groups were tolerated and the yields were from moderate to excellent.
- Liu, Jing,Liang, Bo,Shu, Dongxu,Hu, Yanhe,Yang, Zhen,Lei, Aiwen
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p. 9581 - 9584
(2008/12/22)
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- Direct conversion of aromatic ketones to arenecarboxylic esters via carbon-carbon bond-cleavage reactions
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Aromatic methyl ketones, ss-keto esters, and trifluoromethyl-l,3- diketones can be directly converted to arene-carboxylic esters via carbon-carbon bond cleavage of pyridinium iodide intermediates in the presence of copper(II) oxide, iodine, pyridine, and potassium carbonate in alcoholic media. The advantages of the present method in terms of good yields, mild reaction conditions, and inexpensive reagents should make this protocol a valuable alternative to the existing methods.
- Yin, Guodong,Gao, Meng,Wang, Zihua,Wu, Yandong,Wu, Anxin
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experimental part
p. 369 - 372
(2009/04/07)
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- Efficient esterification of carboxylic acids and phosphonic acids with trialkyl orthoacetate in ionic liquid
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An operationally simple, inexpensive, efficient, and environmentally friendly esterification of various carboxylic acids, phosphonic acids, and phosphinic acids with triethyl orthoacetate or trimethyl orthoacetate under neutral conditions in a typical room temperature ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate, was successfully carried out to provide the corresponding ethyl esters or methyl esters in high yields.
- Yoshino, Tomonori,Imori, Satomi,Togo, Hideo
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p. 1309 - 1317
(2007/10/03)
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- Environmentally friendly esterification of carboxylic acids with triethyl orthoacetate in ionic liquid
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An operationally simple, inexpensive, efficient, and environmentally friendly esterification of carboxylic acids with triethyl orthoacetate under neutral conditions in a typical room temperature ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate, was carried out to provide the corresponding ethyl esters in high yields.
- Yoshino, Tomonori,Togo, Hideo
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p. 1604 - 1606
(2007/10/03)
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- Fe2(SO4)3·4H 2O/concentrated H2SO4: An efficient catalyst for esterification
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The mixed catalyst system, Fe2(SO4) 3·4H2O/concentrated H2SO4 has been applied to catalyse effectively the esterification of α,β-unsaturated acids, aliphatic acids and heterocyclic aromatic acids with ethanol and methanol.
- Liang, Yong-Min,Xu, Qi-Hai,Wu, Xiao-Li,Ma, Yong-Xiang
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p. 226 - 227
(2007/10/03)
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- A simple and facile carboxylation method and its application for synthesis of liquid crystals
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Sonication of a mixture of magnesium powder, 1,2-dibromoethane, aryl bromide and diethyl dicarbonate in THF followed by treatment with BF 3·OEt2 at room temperature afforded aryl ester with reasonable yield. A series of aryl bromides were investigated and transformed to their corresponding aryl esters under the reaction conditions.
- Lee, Adam Shih-Yuan,Wu, Chih-Chiang,Lin, Li-Shin,Hsu, Hsiu-Fu
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p. 568 - 572
(2007/10/03)
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- Synthesis of aromatic esters catalyzed by palladium on charcoal: An efficient heterogeneous catalyst for alkoxycarbonylation of aryl iodides
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Palladium on charcoal was found to catalyze the carbonylation of aryl iodides with various aliphatic alcohols as well as less reactive phenols to give the corresponding esters in high yield at 140°C and in the presence of carbon monoxide (1.0 MPa). The carbonylation-polycondensation of 2,7-diiodo-9,10-dihydrophenanthrene with bisphenol-A afforded high molecular weight polyarylate, poly [oxy-1,4-phenylene (1-methylethylidene)-1,4-phenyleneoxycarbonyl (9,10-dihydro-2,7-phenanthrenediyl) carbonyl].
- Ramesh, Chinnasamy,Nakamura, Ryo,Kubota, Yoshihiro,Miwa, Minoru,Sugi, Yoshihiro
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p. 501 - 504
(2007/10/03)
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- Highly selective and efficient catalyst for carbonylation of aryl iodides: Dimeric palladium complex containing carbon-palladium covalent bond
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Dimeric cyclometallated oxime palladium complex containing palladium-carbon covalent bond was found to efficiently catalyze the carbonylation reactions of aryl iodides with various alcohols to give esters in excellent yields with high selectivity. These complexes were also stable under a carbon monoxide atmosphere at high temperatures.
- Ramesh, Chinnasamy,Kubota, Yoshihiro,Miwa, Minoru,Sugi, Yoshihiro
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p. 2171 - 2173
(2007/10/03)
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- Solvolyses of naphthoyl chlorides. Solvent effect and Grunwald-Winstein correlation analyses with YxBnCl scales
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The solvolyses of 1-naphthoyl (2), 2-naphthoyl (3), 4-methyl-1-naphthoyl (4) and 6-methoxy-2-naphthoyl (5) chlorides in a variety of solvents were studied, and correlation analyses by using the single- and dual-parameter Grunwald-Winstein equations were examined. An excellent linear relationship (R = 0.995) for 4, log (k/k0) = 0.733YxBnCl + 0.269NOTs, was observed. An SN1-like mechanism with decreasing extent of nucleophilic solvent participation was found in the solvolysis of 2 and 4.2-Naphthoyl chloride is likely to have a mechanism at the borderline of SN1-like dissociation and an addition-elimination process. 6-Methoxy-2-naphthoyl chloride shows more SN1-like character than 3 and is associated with nucleophilic solvent intervention more pronounced than that for 2 and 4. The applicability and the advantages of using the YxBnCl scale for different types of substrates are discussed. Copyright
- Liu, Kwang-Ting,Hwang, Patty Y.-H.,Chen, Hun-I.
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p. 750 - 757
(2007/10/03)
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- EPR Studies on Carboxylic Esters. Part 15. Spin Density Distribution in the Radical Anions of Naphthalenecarboxylic Esters
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Persistent radical anions of naphthalene mono-, di-, and tetracarboxylic esters are generated by in situ electroreduction.The spin density distribution is determined from the proton hfs coupling constants as measured by EPR spectroscopy and is discussed in terms of semi-empirical MO calculations.
- Strey, Karsten,Voes, Juergen
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p. 648 - 682
(2007/10/03)
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- Facile esterification of sulfonic acids and carboxylic acids with triethylorthoacetate
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Triethylorthoacetate was found to be surprisingly more effective than triethylorthoformate in the esterification of sulfonic acids and carboxylic acids. Using this reagent, esters of sulfonic and carboxylic acids are prepared in high yields.
- Trujillo, John I.,Gopalan, Aravamudan S.
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p. 7355 - 7358
(2007/10/02)
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- Oxidative conversion of aldoximes into carboxylic acid esters
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Aromatic and aliphatic aldoximes or their O-methyl ethers can be efficiently converted into the corresponding carboxylic acid esters by treatment with an alcoholic solution of 30% hydrogen peroxide in the presence of catalytic amounts of 2-nitrobenzeneseleninic acid. Primary alcohols give excellent to good yields, secondary ones - good to moderate, but with tertiary alcohols no esterification is observed.
- Said,Skarzewski,Mlochowski
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p. 1851 - 1862
(2007/10/02)
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