- Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite
-
In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.
- Cheng, Xionglve,Jiang, Gangzhong,Li, Xingxing,Tao, Suyan,Wan, Xiaobing,Zhao, Yanwei,Zheng, Yonggao
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supporting information
p. 2713 - 2718
(2021/06/25)
-
- Preparation method of carboxylic ester compound
-
The invention relates to a preparation method of a carboxylic ester compound, which comprises the following steps: reacting carboxylic acid with methanol in air under the catalysis of nitrite to obtain an ester compound, the preparation method disclosed by the invention has the advantages of rich raw material sources, cheap and easily available catalyst, mild reaction conditions, simplicity and convenience in operation and the like, a series of fatty carboxylic acids can be modified with high yield, and particularly, the traditional esterification method is generally not suitable for esterification of drug molecules. By utilizing the method, a series of known drug molecules can be modified, so that a shortcut is provided for discovering new drug molecules.
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-
Paragraph 0027-0028
(2021/03/30)
-
- CHEMOSELECTIVE METHYLENE HYDROXYLATION IN AROMATIC MOLECULES
-
A chemoselective and reactive Mn(CF3-PDP) catalyst system that enables for the first time the strategic advantages of late-stage aliphatic C—H hydroxylation to be leveraged in aromatic compounds. This discovery will benefit small molecule therapeutics by enabling the rapid diversification of aromatic drugs and natural products and identification of their metabolites.
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-
Paragraph 0129; 0220
(2020/03/28)
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- Hydroarylation of Alkenes by Protonation/Friedel-Crafts Trapping: HFIP-Mediated Access to Per-aryl Quaternary Stereocenters
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Upon treatment with a combination of HFIP and an organic sulfonic acid, alkenes behave as Br?nsted bases and protonate to give carbocations which can be trapped by electron-rich arenes. The reaction constitutes a Friedel-Crafts hydroarylation which procee
- Nielsen, Christian D.-T.,White, Andrew J. P.,Sale, David,Bures, Jordi,Spivey, Alan C.
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p. 14965 - 14973
(2019/11/13)
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- Ni-Catalyzed Reductive C-O Bond Arylation of Oxalates Derived from α-Hydroxy Esters with Aryl Halides
-
A Ni-catalyzed reductive cross-coupling of α-hydroxycarbonyl compounds modified with oxalyl groups and aryl halides has been developed that furnishes α-aryl esters under mild conditions and tolerates a variety of functionalized aryl halides bearing electron-withdrawing and -donating groups. This work highlights C-O bond fragmentation on secondary alkyl carbon centers that generates α-carbonyl radicals.
- Gao, Mengyu,Sun, Deli,Gong, Hegui
-
supporting information
p. 1645 - 1648
(2019/03/11)
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- Ruthenium(II)-Catalyzed C?H Difluoromethylation of Ketoximes: Tuning the Regioselectivity from the meta to the para Position
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A highly para-selective CAr?H difluoromethylation of ketoxime ethers under ruthenium catalysis has been developed. A wide variety of ketoxime ethers are compatible with the reaction, which leads to the corresponding para-difluoromethylated products in moderate to good yield. A mechanistic study clearly showed that chelation-assisted cycloruthenation is the key factor in the para selectivity of the difluoromethylation of ketoxime ethers. Density functional theory was used to gain a theoretical understanding of the para selectivity.#.
- Yuan, Chunchen,Zhu, Lei,Zeng, Runsheng,Lan, Yu,Zhao, Yingsheng
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supporting information
p. 1277 - 1281
(2018/01/05)
-
- 1, 2, 4-oxadiazole incorporated ketoprofen analogues in search of safer non-steroidal anti-inflammatory agents: Design, syntheses, biological evaluation and molecular docking Studies
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Background: Improving the gastrointestinal safety profile of Non-Steroidal Anti- Inflammatory Drugs (NSAIDs) is an important goal. An important strategy to develop NSAIDs with minimal Gastrointestinal (GI) toxicity is to target the COX-2 isoform with a se
- Ranjan, Chanda,Kumar, Jagdish,Sharma, Kalicharan,Akhter, Mymoona,Siddiqui, Anees A.,Chawla, Gita
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p. 590 - 601
(2018/06/06)
-
- A general approach to intermolecular carbonylation of arene C-H bonds to ketones through catalytic aroyl triflate formation
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The development of metal-catalysed methods to functionalize inert C-H bonds has become a dominant research theme in the past decade as an approach to efficient synthesis. However, the incorporation of carbon monoxide into such reactions to form valuable ketones has to date proved a challenge, despite its potential as a straightforward and green alternative to Friedel-Crafts reactions. Here we describe a new approach to palladium-catalysed C-H bond functionalization in which carbon monoxide is used to drive the generation of high-energy electrophiles. This offers a method to couple the useful features of metal-catalysed C-H functionalization (stable and available reagents) and electrophilic acylations (broad scope and selectivity), and synthesize ketones simply from aryl iodides, CO and arenes. Notably, the reaction proceeds in an intermolecular fashion, without directing groups and at very low palladium-catalyst loadings. Mechanistic studies show that the reaction proceeds through the catalytic build-up of potent aroyl triflate electrophiles.
- Kinney, R. Garrison,Tjutrins, Jevgenijs,Torres, Gerardo M.,Liu, Nina Jiabao,Kulkarni, Omkar,Arndtsen, Bruce A.
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p. 193 - 199
(2018/02/06)
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- Sequential meta-/ortho-C-H Functionalizations by One-Pot Ruthenium(II/III) Catalysis
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Sequential twofold meta-C-H/ortho-C-H functionalization was achieved by means of versatile ruthenium(II) biscarboxylate catalysis. The double C-H activation proved viable in a one-pot fashion with the assistance of synthetically useful imidates. The operationally simple twofold C-H functionalization occurred with high levels of positional selectivity control and was conducted in a nonsequential manner by the judicious choice of the reaction temperature. Detailed experimental mechanistic studies, including unprecedented electron paramagnetic resonance (EPR) experiments, provided strong support for homolytic C-X bond cleavage and facile C-H ruthenation, while a computational density functional theory (DFT) analysis was supportive of a novel mechanistic scenario involving synergistic catalysis via cyclometalated ruthenium(III) complexes as key intermediates.
- Korvorapun, Korkit,Kaplaneris, Nikolaos,Rogge, Torben,Warratz, Svenja,Stückl, A. Claudia,Ackermann, Lutz
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p. 886 - 892
(2018/02/14)
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- A Convenient Ruthenium-Catalysed α-Methylation of Carbonyl Compounds using Methanol
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An efficient ruthenium catalyst is reported, for the first time, to catalyse the α-methylation of ketones and esters using methanol as a green methylating agent. The in situ generated catalyst from the complexes [RuCp*Cl2]2or [RuCp*Cl2]nwith dpePhos provided up to quantitative yields in the presence of only 20 mol% of lithium tert-butoxide (LiO-t-Bu) as a base. Regioselective mono- or multi-methylation could be effectively controlled by temperature. This catalyst system was also effective for the one-pot sequential α-alkylation–α-methylation of methyl ketones and conjugate reduction–α-methylation of α,β-unsaturated ketones to synthesise α-branched ketones. An application of the α-methylation of esters using the ruthenium catalyst was demonstrated for an alternative catalytic synthesis of Ketoprofen. (Figure presented.).
- Dang, Tuan Thanh,Seayad, Abdul Majeed
-
supporting information
p. 3373 - 3380
(2016/11/13)
-
- LONG-ACTING KETOPROFEN COMPOSITIONS
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The invention describes a long-acting veterinary composition comprising at least one ketoprofen ester prodrug. The composition also comprises at least one veterinary acceptable triglyceride, and optionally, at least one preservative, and optionally, at le
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-
Page/Page column 15
(2015/07/07)
-
- Ortho C-H acylation of aryl iodides by palladium/norbornene catalysis
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Reported herein is a palladium/norbornene-catalyzed ortho-arene acylation of aryl iodides by a Catellani-type C-H functionalization. This transformation is enabled by isopropyl carbonate anhydrides, which serve as both an acyl cation equivalent and a hydride source. Double (re)agent: A palladium/norbornene-catalyzed ortho-acylation of aryl iodides was developed, and is enabled by isopropyl carbonate anhydrides, which function as both an acyl cation equivalent and a hydride source. This reaction exhibits excellent functional-group compatibility and broad substrate scope. Heterocycle moieties can be tolerated on both the aryl and acyl partners. FG=functional group.
- Dong, Zhe,Wang, Jianchun,Ren, Zhi,Dong, Guangbin
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supporting information
p. 12664 - 12668
(2015/10/28)
-
- Highly efficient C-H hydroxylation of carbonyl compounds with oxygen under mild conditions
-
A transition-metal-free Cs2CO3-catalyzed α-hydroxylation of carbonyl compounds with O2 as the oxygen source is described. This reaction provides an efficient approach to tertiary α-hydroxycarbonyl compounds, which are highly valued chemicals and widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very environmentally friendly and practical. This transformation is highly efficient and highly selective for tertiary C(sp3)-H bond cleavage. OH, so simple! A transition-metal-free Cs2CO 3-catalyzed α-hydroxylation of carbonyl compounds with O 2 provided a variety of tertiary α-hydroxycarbonyl compounds (see scheme; DMSO=dimethyl sulfoxide), which are widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very efficient and practical.
- Liang, Yu-Feng,Jiao, Ning
-
supporting information
p. 548 - 552
(2014/01/23)
-
- Simultaneous identification of Fenton degradation by-products of diclofenac, ibuprofen and ketoprofen in aquatic media by comprehensive two-dimensional gas chromatography coupled with mass spectrometry
-
Diclofenac, ibuprofen and ketoprofen are anti-inflammatory drugs intensively used both in human and animal treatment. Due to their high stability these compounds are partially removed by wastewater treatment plants and from this reason the development of some alternative treatments such as advanced oxidative processes are necessary. The main problems in the optimization of an advanced oxidative process rise from the difficulties which appear in the identification of degradation by-products necessary for the establishment of degradation pathway. In this paper a developed method for the simultaneous identification of Fenton degradation by-products of the three above mentioned pharmaceuticals is presented. The obtained results show the comprehensive two-dimensional gas chromatography coupled with mass spectrometry as a proper method for the analysis of the complex mixture of compounds resulted from the Fenton degradation process. Moreover, some compounds never mentioned in the scientific literature were identified. (Chemical Equation Presented).
- Beldean-Galea, Mihail Simion,Coman, Virginia,Copaciu, Florina,Thiébaut, Didier,Vial, Jér?me
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p. 1021 - 1027
(2015/07/15)
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- PHTHALIMIDE DERIVATIVES OF NON-STEROIDAL ANTI-INFLAMMATORY COMPOUNDS AND/OR TNF- MODULATORS, METHOD FOR PRODUCING SAME, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AND USES THEREOF FOR THE TREATMENT OF INFLAMMATORY DISEASES
-
The present invention relates to phthalimide derivatives of non-steroidal and/or TNF-α modulating anti-inflammatory compounds as well as the process of obtaining the so-called derivatives, pharmaceutical compositions containing such derivatives and their uses, including use in the treatment of inflammatory diseases, especially those related to chronic inflammatory processes, such as rheumatoid arthritis and intestinal inflammatory diseases (for instance, Chron's disease) and the use of the referred to pharmaceutical compositions as antipyretic, analgesic and platelet antiaggregating medications.
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Page/Page column 32
(2012/03/08)
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- PHTHALIMIDE DERIVATIVES OF NON-STEROIDAL ANTI-INFLAMMATORY COMPOUNDS AND/OR TNF-ALPHA MODULATORS, METHOD FOR PRODUCING SAME, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AND USES THEREOF FOR THE TREATMENT OF INFLAMMATORY DISEASES
-
The present invention relates to phthalimide derivatives of non-steroidal and/or TNF-α modulating anti-inflammatory compounds as well as the process of obtaining the so-called derivatives, pharmaceutical compositions containing such derivatives and their uses, including use in the treatment of inflammatory diseases, especially those related to chronic inflammatory processes, such as rheumatoid arthritis and intestinal inflammatory diseases (for instance, Chron's disease) and the use of the referred to pharmaceutical compositions as antipyretic, analgesic and platelet antiaggregating medications.
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Page/Page column 44
(2012/05/20)
-
- Synthesis and evaluation of anti-inflammatory and analgesic activity of 3-[(5-substituted-1,3,4-oxadiazol-2-yl-thio)acetyl]-2H-chromen-2-ones
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A novel series of 3-[(5-substituted-1,3,4-oxadiazol- 2-yl-thio)acetyl]-2H- chromen-2-one (7a-i) were synthesized by the condensation between the appropriately substituted 5-substituted-1,3,4-oxadiazolyl-2-thione (4a-i) derived from various existing NSAIDs and 3-(2-bromoacetyl)- 2H-chromen-2-one (6) under reflux in the presence of sodium ethoxide. Structure of the synthesized compounds was established on the basis of physicochemical, elemental analysis, and spectral data. The title compounds were screened for in vivo acute anti-inflammatory and analgesic activities at a dose of 200 mg/kg bw. Among the series, four compounds 7c, 7e, 7f, and 7h were found to possess a significant anti-inflammatory and analgesic activity profile. In addition, these compounds were also found to possess a less degree of ulcerogenic potential as compared to standard NSAIDs. Springer Science+Business Media, LLC 2010.
- Ingale, Nista,Maddi, Veeresh,Palkar, Mahesh,Ronad, Pradeepkumar,Mamledesai, Shivalingrao,Vishwanathswamy,Satyanarayana, Darbhamulla
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experimental part
p. 16 - 36
(2012/06/04)
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- Substrate-selective inhibition of cyclooxygenase-2: Development and evaluation of achiral profen probes
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Cyclooxygenase-2 (COX-2) oxygenates arachidonic acid and the endocannabinoids 2-arachidonoylglycerol (2-AG) and arachidonoylethanolamide (AEA). We recently reported that (R)-profens selectively inhibit endocannabinoid oxygenation but not arachidonic acid oxygenation. In this work, we synthesized achiral derivatives of five profen scaffolds and evaluated them for substrate-selective inhibition using in vitro and cellular assays. The size of the substituents dictated the inhibitory strength of the analogs, with smaller substituents enabling greater potency but less selectivity. Inhibitors based on the flurbiprofen scaffold possessed the greatest potency and selectivity, with desmethylflurbiprofen (3a) exhibiting an IC50 of 0.11 μM for inhibition of 2-AG oxygenation. The crystal structure of desmethylflurbiprofen complexed to mCOX-2 demonstrated a similar binding mode to other profens. Desmethylflurbiprofen exhibited a half-life in mice comparable to that of ibuprofen. The data presented suggest that achiral profens can act as lead molecules toward in vivo probes of substrate-selective COX-2 inhibition.
- Windsor, Matthew A.,Hermanson, Daniel J.,Kingsley, Philip J.,Xu, Shu,Crews, Brenda C.,Ho, Winnie,Keenan, Catherine M.,Banerjee, Surajit,Sharkey, Keith A.,Marnett, Lawrence J.
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supporting information
p. 759 - 763
(2012/10/29)
-
- Amide conjugates of ketoprofen and indole as inhibitors of Gli1-mediated transcription in the Hedgehog pathway
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We have previously reported small-molecule inhibitors of Gli1-mediated transcription, an essential down-stream element of the Hh pathway. We created new derivatives of the previous compounds aiming to improve the druggable properties. The new compounds, a
- Mahindroo, Neeraj,Connelly, Michele C.,Punchihewa, Chandanamali,Yang, Lei,Yan, Bing,Fujii, Naoaki
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experimental part
p. 4801 - 4811
(2010/08/06)
-
- Enzymatic production of l-menthol by a high substrate concentration tolerable esterase from newly isolated Bacillus subtilis ECU0554
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Enzymatic preparation of l-menthol has been attracting much attention in the flavor and fragrance industry. A new ideal strain, Bacillus subtilis ECU0554, which exhibited high hydrolytic activity and excellent enantioselectivity towards l-menthyl ester, has been successfully isolated from soil samples through enrichment culture and identified as Bacillus subtilis by 16S rDNA gene sequencing. The esterase extracted from B. subtilis ECU0554 (BSE) showed the best catalytic properties (E > 200) for dl-menthyl acetate among the five menthyl esters examined. Enantioselective hydrolysis of 100 mM dl-menthyl acetate at 30°C and pH 7.0, using crude BSE as biocatalyst and 10% ethanol (v/v) as cosolvent, resulted in 49.0% conversion (3 h) and 98.0% ee for the l-menthol produced, which were much better than those using commercial enzymes tested. Moreover, BSE exhibited strong tolerance against high substrate concentration (up to 500 mM), and the concentration of l-menthol produced could reach as high as 182 mM, and more importantly, the optical purity of l-menthol produced was kept above 97% ee, which were not found in previous reports. These results imply that BSE is a potentially promising bio-catalyst for the large-scale enzymatic preparation of l-menthol. Using this excellent biocatalyst, the enzymatic production of l-menthol will become a mild, efficient, inexpensive and easy-to-use "green chemistry" methodology.
- Zheng, Gao-Wei,Yu, Hui-Lei,Zhang, Jian-Dong,Xu, Jian-He
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experimental part
p. 405 - 414
(2009/11/30)
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- (R,S)-azolides as novel substrates for lipase-catalyzed hydrolytic resolution in organic solvents
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Azolides, that is, N-acylazoles, as versatile acylation reagents are well characterized in the literature, in which the azole structure can not only act as a better leaving group but also make the carbonyl carbon more electrophilic and susceptible to nucleophilic attack. It is therefore desirable to combine this unique property and lipase resolution ability in the development of a new resolution process for preparing optically pure carboxylic acids. With the Candida antarctica lipase B (CALB)-catalyzed hydrolysis of (R,S)-N- profenylazoles in organic solvents as the model system, (R,S)-N-profenyl-l,2,4- triazoles instead of their corresponding ester analogues were exploited as the best substrates for preparing optically pure profens, i.e., 2-arylpropionic acids. The structure-reactivity correlations for the (R,S)-azolides in water-saturated methyl tert-butyl ether (MTBE) at 45°C coupled with a thorough kinetic analysis were further employed for elucidating the rate-limiting formation of a tetrahedral adduct without C-N bond breaking or with moderate C-N bond breaking concerted with C-O bond formation in the acylation step. The advantages of easy substrate preparation, high enzyme reactivity and enantioselectivity, and easy recovery of the product and remaining substrate by aqueous extraction demonstrate the potential of using (R,S)-azolides as novel substrates for the enzymatic resolution process.
- Wang, Pei-Yun,Chen, Ying-Ju,Wu, An-Chi,Lin, Yi-Sheng,Kao, Min-Fang,Chen, Jin-Ru,Ciou, Jyun-Fen,Tsai, Shau-Wei
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supporting information; experimental part
p. 2333 - 2341
(2009/12/27)
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- An efficient and practical sequential one-pot synthesis of suprofen, ketoprofen and other 2-arylpropionic acids
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A novel sequential double carbonylation to synthesize anti-inflammatory drugs such as Ketoprofen and Suprofen has been developed. Starting from easily available aryl halides and arylboronic acids a one-pot carbonylative Suzuki and hydroxycarbonylation reaction sequence proceeds in good selectivity and high yield in the presence of the palladium/cataCXium A catalyst system. Applying optimized conditions different 2-arylpropionic acids were synthesized in good yields.
- Neumann, Helfried,Brennfuehrer, Anne,Beller, Matthias
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experimental part
p. 2437 - 2442
(2009/10/06)
-
- Synthesis and pharmacological evaluation of imidazole derivatives of some non-steroidal anti-inflammatory drugs
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A series of imidazole derivatives of NSAIDs (4a-l) have been prepared by condensation of NSAIDs hydrazides (1,2) with substituted oxazolones and evaluated for anti-inflammatory and gastrointestinal toxicity, which showed good anti-inflammatory activity and reduced gastrointestinal toxicity as compared to parent drug.
- Parcha, Versha,Kaur, Jaswinder,Gupta, Vinay,Anroop
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experimental part
p. 321 - 325
(2009/06/25)
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- Design of noncompetitive interleukin-8 inhibitors acting on CXCR1 and CXCR2
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Chemokines CXCL8 and CXCL1 play a key role in the recruitment of neutrophils at the site of inflammation. CXCL8 binds two membrane receptors, CXCR1 and CXCR2, whereas CXCL1 is a selective agonist for CXCR2. In the past decade, the physiopathological role of CXCL8 and CXCL1 has been investigated. A novel class of small molecular weight allosteric CXCR1 inhibitors was identified, and reparixin, the first drug candidate, is currently under clinical investigation in the prevention of ischemia/reperfusion injury in organ transplantation. Reparixin binding mode to CXCR1 has been studied and used for a computer-assisted design program of dual allosteric CXCR1 and CXCR2 inhibitors. In this paper, the results of modeling-driven SAR studies for the identification of potent dual inhibitors are discussed, and three new compounds (56, 67, and 79) sharing a common triflate moiety have been selected as potential leads with optimized pharmacokinetic characteristics.
- Moriconi, Alessio,Cesta, Maria Candida,Cervellera, Maria Neve,Aramini, Andrea,Coniglio, Silvia,Colagioia, Sandro,Beccari, Andrea Rosario,Bizzarri, Cinzia,Cavicchia, Michela Rita,Locati, Massimo,Galliera, Emanuela,Di Benedetto, Paola,Vigilante, Paolo,Bertini, Riccardo,Allegretti, Marcello
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p. 3984 - 4002
(2008/02/11)
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- Carbanion-mediated photocages: Rapid and efficient photorelease with aqueous compatibility
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A new photocage is proposed, based on ketoprofen-derived compounds and mediated by carbanions. The new photocage has significant advantages over the widely used o-nitrobenzyl derivatives, including aqueous compatibility, faster photorelease, higher quantu
- Lukeman, Matthew,Scaiano, Juan C.
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p. 7698 - 7699
(2007/10/03)
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- 2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors
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The CXC chemokine CXCL8/IL-8 plays a major role in the activation and recruitment of polymorphonuclear (PMN) cells at inflammatory sites. CXCL8 activates PMNs by binding the seven-transmembrane (7-TM) G-protein-coupled receptors CXC chemokine receptor 1 (CXCR1) and CXC chemokine receptor 2 (CXCR2). (R)-Ketoprofen (1) was previously reported to be a potent and specific noncompetitive inhibitor of CXCLS-induced human PMNs chemotaxis. We report here molecular modeling studies showing a putative interaction site of 1 in the TM region of CXCR1. The binding model was confirmed by alanine scanning mutagenesis and photoaffinity labeling experiments. The molecular model driven medicinal chemistry optimization of 1 led to a new class of potent and specific inhibitors of CXCL8 biological activity. Among these, repertaxin (13) was selected as a clinical candidate drug for prevention of post-ischemia reperfusion injury.
- Allegretti, Marcello,Bertini, Riccardo,Cesta, Maria Candida,Bizzarri, Cinzia,Di Bitondo, Rosa,Di Cioccio, Vito,Galliera, Emanuela,Berdini, Valerio,Topai, Alessandra,Zampella, Giuseppe,Russo, Vincenzo,Di Bello, Nicoletta,Nano, Giuseppe,Nicolini, Luca,Locati, Massimo,Fantucci, Piercarlo,Florio, Saverio,Colotta, Francesco
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p. 4312 - 4331
(2007/10/03)
-
- Synthesis and optical resolution of 2-aryl-2-fluoropropionic acids, fluorinated analogues of Non-steroidal Anti-inflammatory Drugs (NSAIDs)
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We report the synthesis of optically active 2-aryl-2-fluoropropionic acids 2 as non-epimerizable mimics of 2-arylpropionic acids 1, a class of compounds which have been widely used as non-steroidal anti-inflammatory drugs (NSAIDs). This is a continuation of our research involving the design, synthesis, and evaluation of chiral fluorine-containing organic molecules as effective analogues of pharmacologically important compounds.
- Fujisawa, Hidehito,Fujiwara, Tomoya,Takeuchi, Yoshio,Omata, Kenji
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p. 524 - 528
(2007/10/03)
-
- Absolute rate constants for water protonation of 1-(3-benzoylphenyl)alkyl carbanions.
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[reaction: see text] Efficient photodecarboxylation of (3-benzoylphenyl)alkanoic acids with formation of carbanions has enabled the determination of their protonation rate constants in water; the values obtained show that the reactivity toward protonation
- Cosa, Gonzalo,Llauger, Laura,Scaiano,Miranda, Miguel A
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p. 3083 - 3085
(2007/10/03)
-
- Stable isotope labelling and determination of ketoprofen in human plasma and urine by gas chromatography/negative ion chemical ionization mass spectrometry
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A method for the quantitative measurement of the non-steroidal anti-inflammatory drug ketoprofen in human plasma and urine is presented. The assay is based on gas chromatography/negative ion chemical ionization mass spectrometry. The preparation of stable isotope-labelled ketoprofen for use as an internal standard is described. After solvent extraction from the acidified matrix, urine samples were analysed as pentafluorobenzyl esters, whereas plasma samples required further derivatization to the hydroxylamine-trimethylsilyl derivatives. The detection limit was found to be 5 pg in both cases. The method was applied to the pharmacokinetics of ketoprofen in man after epidermal application.
- Leis,Leis,Windischhofer
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p. 486 - 492
(2007/10/03)
-
- Substituted diphenylmethane derivatives as analgesic or anti-inflammatory agents
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A compound of formula I or a pharmaceutically acceptable salt thereof STR1 where --R1 is hydrogen or methyl; --X-- is --CO-- or --CH2 --; --Y-- is >CH--A or its vinylogous group >C=CH--CH2 --A, wherein --A is a --NR4
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-
- Pharmaceutically useful derivatives of thiazolidine-4-carboxylic acid
-
Compounds of formula in which R, R1 and Y have the meanings shown in the description, their preparation by condensing an aldehyde or a ketone with cysteine or a derivative thereof and their use in the pharmaceutical field. The compounds of formula I possess antipyretic, anti--inflammatory, mucolytic and analgesic activity together with a low capacity to cause gastric injuries. The compounds of formula I, furthermore, are particularly useful in the treatment of ischemia and reperfusion syndromes.
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- A Simple and Efficient Conversion of Aldehyde Acetals into Esters
-
The reaction of aldehydic acetals with hypochlorous acid in acetic acid-acetone afforded the corresponding esters in excellent yields.From cyclic acetals, only the corresponding hydroxyalkyl esters were obtained.Keywords - acetal; hypochlorite; hypochlorous acid; conversion; ester; hydroxyalkyl ester; regioselectivity
- Sugai, Saburo,Kodama, Takashi,Akaboshi, Sanya,Ikegami, Shiro
-
-
- Asymmemtric Hydrolysis of (+/-)-α-Substituted Carboxylic Acid Esters with Microorganisms
-
Microorganisms that hydrolyze methyl 2-phenylpropionate (1) or reduce 4-phenyl-2-butanone (3) were screened from 250 type cultures.Several Aspergilli and two bacteria hydrolyzed ester 1, and Asp. sojae IAM 2703 preferentially hydrolyzed (R)-isomer of (+/-)-1, whereas Bacillus subtilis var. niger IFO 3108 and Mycobacterium smegmatis ATCC 10143 preferentially hydrolyzed (S)-isomer.The hydrolysis of the related esters of 1 with these organisms was also examined.
- Iriuchijima, Shinobu,Keiyu, Atsuko
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p. 1389 - 1392
(2007/10/02)
-
- Novel α-thio-alkanoic acid derivatives
-
Novel α-thio-alkanoic acid derivatives and a process for their preparation. These novel compounds can be easily converted to useful medicines.
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-
- 4-(M-benzoylphenyl)butyric acid derivatives
-
Novel butyric acid derivatives of the formula SPC1 Wherein X, X1, X2 and X3 are individually selected from the group consisting of hydrogen, halogen, lower alkyl of 1 to 5 carbon atoms, lower alkoxy of 1 to 5 carbon atoms, lower alkylthio of 1 to 5 carbon atoms, trifluoromethoxy, trifluoromethylthio, trifluoromethyl, OH and dilower alkylamino of 1 to 5 carbon atoms for each alkyl, R is selected from the group consisting of hydrogen, lower alkyl of 1 to 5 carbon atoms, o-carboxyphenyl, 2,3-dihydroxypropyl and -CH2 -CH - CH2 EQU1 wherein P and Q are individually lower alkyl of 1 to 5 carbon atoms, Z and X4 are individually selected from the group consisting of hydrogen and lower alkyl of 1 to 5 carbon atoms and Y is selected from the group consisting of hydrogen and --OH and the dotted line indicates the optional presence of a double bond when Y is hydrogen and when R is hydrogen or o-carboxyphenyl, the salts thereof with a non-toxic pharmaceutically acceptable mineral or organic base, which compounds have anti-inflammatory and analgesic activity and are substantially devoid of ulcerigenic activity and their preparation and novel intermediates formed therein.
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