- Synthesis of 5,10,15,20-tetrakis(2-amino-5-methoxyphenyl)-porphyrin: A versatile building block for porphyrin face selection
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A new bis-faced substituted porphyrin has been prepared. The four hydroxyl groups on one side as well as the four amino functions on the other one allow at will, a different functionalization of each face of the macrocycle. The usefulness of this synthon is illustrated.
- Ruzié, Christian,Gueyrard, David,Boitrel, Bernard
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Read Online
- Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer
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Evodiamine (Evo) is a quinazolinocarboline alkaloid found in Evodia rutaecarpa and exhibits moderate antiproliferative activity. Herein, we report using a scaffold-hopping approach to identify a series of novel polycyclic heterocyclic derivatives based on Evo as the topoisomerase I (Top1) inhibitor for the treatment of triple-negative breast cancer (TNBC), which is an aggressive subtype of breast cancer with limited treatment options. The most potent compound 7f inhibited cell growth in a human breast carcinoma cell line (MDA-MB-231) with an IC50 value of 0.36 μM. Further studies revealed that Top1 was the target of 7f, which directly induced irreversible Top1-DNA covalent complex formation or induced an oxidative DNA lesion through an indirect mechanism mediated by reactive oxygen species. More importantly, in vivo studies showed that 7f exhibited potent antitumor activity in a TNBC-patient-derived tumor xenograft model. These results suggest that compound 7f deserves further investigation as a promising candidate for the treatment of TNBC.
- Chen, Zhe-Sheng,Li, Dahong,Qiu, Yangyi,Wu, Liang,Xu, Jinyi,Xu, Shengtao,Yang, Dong-Hua,Yao, Hong,Zhou, Manzhen
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p. 17346 - 17365
(2021/12/09)
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- Iron-Catalyzed Reductive Cyclization by Hydromagnesiation: A Modular Strategy Towards N-Heterocycles
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A reductive cyclization to prepare a variety of N-heterocycles, through the use of ortho-vinylanilides, is reported. The reaction is catalyzed by an inexpensive and bench-stable iron complex and generally occurs at ambient temperature. The transformation likely proceeds through hydromagnesiation of the vinyl group, and trapping of the in situ generated benzylic anion by an intramolecular electrophile to form the heterocycle. This iron-catalyzed strategy was shown to be broadly applicable and was utilized in the synthesis of substituted indoles, oxindoles and tetrahydrobenzoazepinoindolone derivatives. Mechanistic studies indicated that the reversibility of the hydride transfer step depends on the reactivity of the tethered electrophile. The synthetic utility of our approach was further demonstrated by the formal synthesis of a reported bioactive compound and a family of natural products.
- Larin, Egor M.,Lautens, Mark,Loup, Joachim
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p. 22345 - 22351
(2021/09/09)
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- Ursolic acid quinolinyl hydrazide derivative with anti-tumor activity as well as preparation method and application thereof
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The invention discloses an ursolic acid quinolinyl hydrazide derivative with anti-tumor activity as well as a preparation method and application thereof. The invention provides an ursolic acid quinolinyl hydrazide heterocyclic derivative with a structure shown as a general formula I and pharmaceutically acceptable salt thereof: the formula I is shown in the description, wherein I-a: R1 is equal to H and R2 is equal to CH3; I-b: R1 is equal to OMe and R2 is equal to CH3; I-c: R1 is equal to F and R2 is equal to CH3; I-d: R1 is equal to C1 and R2 is equal to CH3; I-e: R1 is equal to H1 and R2 is equal to n-C4H9; I-f: R1 is equal to OMe and R2 is equal to n-C4H9; I-g: R1 is equal to F and R2 is equal to n-C4H9; I-h: R1 is equal to C1 and R2 is equal to n-C4H9. The ursolic acid quinolinyl hydrazide heterocyclic derivative and the pharmaceutically acceptable salt thereof, provided by the invention, have the remarkable anti-tumor activity; a pharmacology experiment shows that the ursolic acid quinolinyl hydrazide derivative disclosed by the invention has a remarkable inhibition effect on human breast cancer cells MDA-MB-231, human cervical cancer cells HeLa and human hepatoma cells SMMC-7721, has low toxicity on human normal epithelial cells QSG-7701 and has a potential of being used for developing anti-tumor drugs.
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Paragraph 0136; 0137; 0138
(2018/01/19)
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- N, N ′-Disubstituted thiourea and urea derivatives: Design, synthesis, docking studies and biological evaluation against nitric oxide synthase
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The synthesis and biological evaluation of new types of N,N′-disubstituted thiourea and urea derivatives as inhibitors of both neuronal nitric oxide synthase (nNOS) and inducible nitric oxide synthase (iNOS) are described. These compounds have been designed by reduction of the carbonyl group in the thiourea and urea kynurenamine derivatives 3 previously synthesized by our research group. The synthetic route performed to this new family also allows us to obtain the molecules 3 with less synthetic steps and higher global yield. Regarding the biological results, in general, the new derivatives 4a-q inhibit the neuronal NOS isoform better than the inducible one. Furthermore, thioureas exhibit higher inhibition than ureas for both isoenzymes. Among all the tested compounds, 4g shows significant nNOS (80.6%) and iNOS (76.6%) inhibition values without inhibiting eNOS. This molecule could be an interesting starting point for the design of new inhibitors with application in neurological disorders where both isoenzymes are implicated such as Parkinson's disease.
- Chayah, Mariem,Camacho, M. Encarnación,Carrión, M. Dora,Gallo, Miguel A.,Romero, Miguel,Duarte, Juan
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p. 667 - 678
(2016/05/19)
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- BIARYLTRIAZOLE INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR
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The present disclosure describes biaryl triazole compounds, as well as their compositions and methods of use. The compounds inhibit the activity of macrophage migration inhibitory factor and are useful for the treatment of diseases, e.g., inflammatory dis
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Page/Page column 187
(2016/09/22)
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- Heterobicyclic sphingosine 1-phosphate analogs
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Compounds that have agonist activity at one or more of the S1P receptors are provided. The compounds are sphingosine analogs that, after phosphorylation, can behave as agonists at S1P receptors.
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Page/Page column
(2014/04/18)
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- SUBSTITUTED BENZOAZEPINES AS TOLL-LIKE RECEPTOR MODULATORS
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Provided are compositions and methods useful for modulation of signaling through the Toll-like receptors TLR7 and/or TLR8. The compositions and methods have use in treating or preventing disease, including cancer, autoimmune disease, fibrotic disease, cardiovascular disease, infectious disease, inflammatory disorder, graft rejection, or graft-versus-host disease.
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Page/Page column 61
(2012/07/28)
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- Design and synthesis of 6,6-fused heterocyclic amides as raf kinase inhibitors
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Compounds belonging to several scaffolds-quinazolines, quinolines and quinoxalines-were designed and synthesized as Raf kinase inhibitors. Scaffolds were assessed for in vitro BrafV600E inhibition, and overall kinase selectivity. Pharmacokinetic parameters for one of the scaffolds were also determined.
- Ramurthy, Savithri,Costales, Abran,Jansen, Johanna M.,Levine, Barry,Renhowe, Paul A.,Shafer, Cynthia M.,Subramanian, Sharadha
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supporting information; experimental part
p. 1678 - 1681
(2012/04/04)
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- New photolabile BAPTA-based Ca2+ cages with improved photorelease
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The efficient synthesis, physicochemical and photolytical properties of a photoactivable BAPTA-based Ca2+ cage containing two photosensitive o-nitrobenzhydryl groups attached to the aromatic core are described. Ca 2+ release in livin
- Cui, Jiaxi,Gropeanu, Radu A.,Stevens, David R.,Rettig, Jens,Campo, Aranzazu Del
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experimental part
p. 7733 - 7740
(2012/07/02)
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- Novel acid-type cyclooxygenase-2 inhibitors: Design, synthesis, and structure-activity relationship for anti-inflammatory drug
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Cyclooxygenase (COX) is a key rate-limiting enzyme for prostaglandin (PG) production cascades in the human body. The mechanisms of both the anti-inflammation effects and the side-effects of traditional COX inhibitors are associated with the existence of two COX isoforms. Thus while COX-1 is predominantly expressed ubiquitously and constitutively, and it serves a housekeeping role in processes such as gastrointestinal (GI) mucosa protection, COX-2 is absent or exhibits a low level of expression in most tissues, and is highly upregulated in response to endotoxin, virus, inflammatory or tissue-injury stimuli/signals, and tumour promoter in the various types of organs, tissues, and cells. Furthermore, COX-2 contribution to PGE2 and PGI2 production evokes and sustains systemic or peripheral inflammatory disease, but it is not involved in the COX-1-mediated GI tract events. Also, hypersensitivity of aspirin owing to its inhibitory action against COX-1 is a significant concern clinically. Consequently, highly selective COX-2 inhibitors have been needed for the treatment of inflammatory- and inflammation related-diseases that include pyrexia, inflammation, pain, rheumatoid arthritis, osteoarthritis, and cancers. In this study, a series of novel [2-{[(4-substituted or 4,5-disubstituted)-pyridin-2-yl]carbonyl}-(5- or 6-substituted or 5,6-disubstituted)-1H-indol-3-yl]acetic acid analogues was designed, synthesized, and evaluated to identify potent and selective COX-2 inhibitors as potential agents against inflammatory diseases. As significant findings, the present study clarified unique structure-activity relationship of the analogues toward potent and selective COX-2 inhibition in vitro, and identified 2-{6-fluoro-2-[4-methyl-2-pridinyl)carbonyl]-1H-indol-3-yl}acetic acid as a potent and selective COX-2 inhibitor in vitro that demonstrated orally potent anti-inflammation efficacy against carrageenan-induced oedema formation in the foot of SPF/VAF male SD rats as a peripheral inflammation model in vivo.
- Hayashi, Shigeo,Ueno, Naomi,Murase, Akio,Nakagawa, Yoko,Takada, Junji
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experimental part
p. 179 - 195
(2012/07/27)
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- Step-economical synthesis of tetrahydroquinolines by asymmetric relay catalytic Friedlaender condensation/transfer hydrogenation
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Two steps in one reaction: The title relay reaction relies on a combination of an achiral Lewis acid and a chiral Bronsted acid (B-H in the scheme). This one-pot method provides access to tetrahydroquinoline derivatives with multiple continuous stereogeni
- Ren, Lei,Lei, Tao,Ye, Jia-Xi,Gong, Liu-Zhu
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supporting information; experimental part
p. 771 - 774
(2012/02/05)
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- S1P MODULATING AGENTS
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Compounds of formula (I) or (II) can modulate the activity of SIP receptors.
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- Bronsted acid-catalyzed enantioselective Friedlaender condensations: Achiral amine promoter plays crucial role in the stereocontrol
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A highly enantioselective Friedlaender condensation has been established by using chiral Bronsted acids in combination with achiral amines to give quinolines in high yields (up to 99%) and with excellent enantioselectivities (up to 95%).
- Ren, Lei,Lei, Tao,Gong, Liu-Zhu
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supporting information; experimental part
p. 11683 - 11685
(2011/12/02)
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- Site-selective metal-coordination-based patterning of silane monolayers
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Herein, we report a method to pattern a derivatized nifedipine silane monolayer that aromatizes under UV irradiation. Using a functionalized SCS-Pd(ii) pincer complex, we demonstrate that a strong metal-coordination complex between the aromatized nifedipine derivative and the pincer complex is formed. This methodology integrates SAM photolithography (top-down) and molecular recognition directed self-assembly (bottom-up) strategies to create simple and rapid synthesizable functional patterned surfaces. The Royal Society of Chemistry.
- Li, Minfeng,Wang, Yu,Pinon III, Victor,Weck, Marcus
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supporting information; experimental part
p. 2802 - 2804
(2011/04/24)
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- Synthesis and biological evaluation of novel 7-acyl homocamptothecins as Topoisomerase I inhibitors
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A series of novel 7-acyl derivatives of homocamptothecin (hCPT) were designed and synthesized with the purpose to improve antitumor activity of hCPT, via Minisci free-radical reaction from 10-methoxyhomocamptothecin. All the compounds were evaluated for i
- Liu, Wenfeng,Zhu, Lingjian,Guo, Wei,Zhuang, Chunlin,Zhang, Yongqiang,Sheng, Chunquan,Cheng, Pengfei,Yao, Jianzhong,Wang, Wenya,Dong, Guoqiang,Wang, Shengzheng,Miao, Zhenyuan,Zhang, Wannian
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scheme or table
p. 2408 - 2414
(2011/06/22)
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- NOVEL CURCUMIN DERIVATIVE
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To develop a highly safe measure to treat Alzheimer's disease using a secretase-inhibiting substance, there is provided a compound represented by the following general formula (I) or a salt thereof: wherein A represents a phenyl group or the like, R1 represents a chlorine atom, a bromine atom, or a nitro group or the like, R2, R3, R4, and R5 each represent a hydrogen atom or the like, and L represents CH2—CH2 or CH═CH.
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Page/Page column 10
(2011/04/24)
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- HETEROBICYCLIC SPHINGOSINE 1-PHOSPHATE ANALOGS
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Compounds that have agonist activity at one or more of the SlP receptors are provided. The compounds are sphingosine analogs that, after phosphorylation, can behave as agonists at SlP receptors.
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Page/Page column 45
(2010/05/14)
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- L-Alkyl-4-phenyl-6-alkoxy-1H-quinazolin-2-ones: A novel series of potent calcium-sensing receptor antagonists
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Parathyroid hormone (PTH) is an effective bone anabolic agent. However, only when administered by daily sc injections exposure of short duration is achieved, a prerequisite for an anabolic response. Instead of applying exogenous PTH, mobilization of endogenous stores of the hormone can be envisaged. The secretion of PTH stored in the parathyroid glands is mediated by a calcium sensing receptor (CaSR) a GPCR localized at the cell surface. Antagonists of CaSR (calcilytics) mimic a state of hypocalcaemia and stimulate PTH release to the bloodstream. Screening of the internal compound collection for inhibition of CaSR signaling function afforded 2a. In vitro potency could be improved > 1000 fold by optimization of its chemical structure. The binding mode of our compounds was predicted based on molecular modeling and confirmed by testing with mutated receptors. While the compounds readily induced PTH release after iv application a special formulation was needed for oral activity. The required profile was achieved by using microemulsions. Excellent PK/PD correlation was found in rats and dogs. High levels of PTH were reached in plasma within minutes which reverted to baseline in about 1-2 h in both species.
- Widler, Leo,Altmann, Eva,Beerli, René,Breitenstein, Werner,Bouhelal, Rochdi,Buhl, Thomas,Gamse, Rainer,Gerspacher, Marc,Halleux, Christine,John, Markus R.,Lehmann, Hansjoerg,Kalb, Oskar,Kneissel, Michaela,Missbach, Martin,Müller, Irene R.,Reidemeister, Sibylle,Renaud, Johanne,Taillardat, Agnes,Tommasi, Ruben,Weiler, Sven,Wolf, Romain M.,Seuwen, Klaus
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experimental part
p. 2250 - 2263
(2010/08/21)
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- Toward new camptothecins. Part 6: Synthesis of crucial ketones and their use in Friedl?nder reaction
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In the context of the preparation of camptothecin and luotonin A analogs, the synthesis of some key keto-precursors and their use in Friedl?nder condensation are described. This paper also focuses on the stability of these keto intermediates and emphasizes the major differences between indolizinones and pyrroloquinazolinones series. Noteworthy is also the report of some original structures isolated as by-products of some experiments.
- Gavara, Laurent,Boisse, Thomas,Hénichart, Jean-Pierre,Da?ch, Adam,Rigo, Beno?t,Gautret, Philippe
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experimental part
p. 7544 - 7561
(2010/12/25)
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- NOVEL CURCUMIN DERIVATIVE
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The present invention provides a novel compound that is structurally similar to curcumin and has a suppressive effect on Aβ aggregation, a degradative effect on Aβ aggregates, an inhibitory effect on β-secretase, and a protective effect on neurons. The novel compound is a compound represented by the following general formula (Ia) or a salt thereof: wherein R1 represents a 4-hydroxy-3-methoxyphenyl group or the like, and R2 represents a 1H-indol-6-yl group or the like.
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Page/Page column 95
(2009/12/07)
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- Effect of aldehyde and methoxy substituents on nucleophilic aromatic substitution by [18F]fluoride
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For a series of benzaldehydes only with a leaving group or with both a leaving group and a single methoxy substituent 18F-fluorination via nucleophilic aromatic substitution (SNAr) was studied in DMF and Me2SO. In general, the radiochemical yields were clearly higher in DMF than in Me2SO. In the fluorodehalogenation reaction (leaving group: halogen = Br, Cl), extremely low radiochemical yields were observed in Me2SO (2SO (within 3 min reaction time, 90% of the precursor was consumed; radiochemical yield = 1.0 ± 0.5%); however, in DMF oxidation was always kept at a low level during the entire reaction (13C-NMR ppm values of the aromatic carbon atom bearing the leaving group.
- Shen, Bin,L?ffler, Dirk,Zeller, Klaus-Peter,übele, Michael,Reischl, Gerald,Machulla, Hans-Jürgen
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p. 1461 - 1468
(2008/09/18)
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- 2-Amino and 2′-aminocombretastatin derivatives as potent antimitotic agents
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A novel series of 2-amino and 2′-aminocombretastatin derivatives were synthesized and evaluated for antitumor activity. Several compounds had excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 11, 20, and 21 with ICsu
- Chang, Jang-Yang,Yang, Ming-Fang,Chang, Chi-Yen,Chen, Chi-Ming,Kuo, Ching-Chuan,Liou, Jing-Ping
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p. 6412 - 6415
(2007/10/03)
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- 2,6-Disubstituted quinazolines, quinoxalines, quinolines and isoquinolines and methods of their use as inhibitors of RAF kinase
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New substituted quinazoline, quinoxaline, quinoline and isoquinoline compounds, compositions and methods of inhibition of Raf kinase activity in a human or animal subject are provided. The new compounds compositions may be used either alone or in combination with at least one additional agent for the treatment of a Raf kinase mediated disorder, such as cancer.
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Page/Page column 13; 17
(2010/02/11)
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- A catalytic antibody against a tocopherol cyclase inhibitor
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The cyclic ammonium cation 5 and its guanidinium analogue 4 areinhibitors of tocopherol cyclase. Monoclonal antibodies were raised against protein conjugates of the haptens 1-3 and screened for catalytic reactions with alkene 8, a short chain analogue of
- Manetsch, Roman,Zheng, Lei,Reymond, Martine T.,Woggon, Wolf-Dietrich,Reymond, Jean-Louis
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p. 2487 - 2506
(2007/10/03)
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- Synthesis and structure-activity relationships of thioflavone derivatives as specific inhibitors of the ERK-MAP kinase signaling pathway
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Condensation of nitrobenzaldehydes 3 and α-[o-(p-methoxybenzylthio) benzoyl] sulfoxide 4 gave α-sulfinyl enones 5. Treatment of 5 with formic acid caused cyclization followed by debenzylation to afford 3-(methylsulfinyl) thioflavanones 6. Double-bond formation with elimination of methanesulfenic acid was performed by refluxing 6 in benzene, and, finally, the nitro group of 2-phenyl-4H-1-benzothiopyran-4-one (thioflavones) 7 was reduced with tin in tetrafluoroboric acid. Various 2′-aminothioflavones 8 thus prepared were evaluated for their inhibitory effects on the ERK-MAP kinase pathway. In a cell-based assay, 2-(2′-amino-3 ′-methoxyphenyl)-4H-1-benzothiopyran-4-one (8b) showed a more potent inhibitory effect than the corresponding oxygen compound (PD98059, 1) on the Raf-induced activation of the ERK-MAP kinase pathway as well as cell proliferation. Furthermore, compound 8b selectively and potently inhibited the proliferation of tumor cells in which the ERK-MAP kinase pathway is constitutively activated.
- Kataoka, Tadashi,Watanabe, Shin-Ichi,Mori, Eiji,Kadomoto, Ryoji,Tanimura, Susumu,Kohno, Michiaki
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p. 2397 - 2407
(2007/10/03)
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- HETEROARYL- SUBSTITUTED PYRROLO` 2, 3- B! PYRIDINE DERIVATIVES AS CRF RECEPTOR ANTAGONISTS
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The present invention provides compounds of formula (I) including stereoisomers, prodrugs and pharmaceutically acceptable salts or solvates thereof, to processes for their preparation, to pharmaceutical compositions containing them and to their use in the treatment of conditions mediated by corticotropin-releasing factor (CRF).
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Page/Page column 37
(2010/02/07)
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- Zeolite-supported chromium(VI) oxide: A mild, efficient, and inexpensive reagent for oxidative deprotection of trimethylsilyl ethers under microwave irradiation
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Primary and secondary trimethylsilyl ethers are efficiently converted, to the corresponding carbonyl compounds using HZSM-5 zeolite-supported CrO 3 under microwave irradiation in solventless system.
- Heravi, Majid M.,Hydarzadeh, Fereshteh,Farhangi, Yahya,Ghassemzadeh, Mitra
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p. 1473 - 1475
(2007/10/03)
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- Studies on new platelet aggregation inhibitors 1. Synthesis of 7-nitro-3,4-dihydroquinoline-2(1H)-one derivatives
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A series of 6-cyclic aliphatic amino-7-nitro-3,4-dihydroquinoline-2(1H)-ones were prepared and tested for platelet aggregation inhibitory effect, cardiotonic activity and chronotropic activity. These compounds appeared to show selective inhibitory activity against platelet aggregation. Among them, 6-(4-ethoxycarbonylpiperidino)-7-nitro-3,4-dihydroquinoline-2(1H)-one (22f) showed the most potent inhibitory activity and high selectivity. A divergent synthetic route to 6-cyclic aliphatic amino-7-nitro-3,4-dihydroquinoline-2(1H)-one derivatives has also been investigated.
- Iyobe,Uchida,Kamata,Hotel,Kusama,Harada
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p. 822 - 829
(2007/10/03)
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- Transition metal complexes in organic synthesis, part 36. Cyclization of tricarbonyliron complexes by oxygen to 4a,9a-Dihydro-9H-carbazoles: Application to the synthesis of mukonine, mukonidine, and pyrido[3,2,1-jk]carbazoles
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Aryl-substituted tricarbonyl(η4-cyclohexa-1,3-diene)iron complexes are oxidatively cyclized in protic medium in the air to tricarbonyliron-complexed 4a,9a-dihydro-9H-carbazoles. The method is applied to the total synthesis of mukonine and mukon
- Knoelker, Hans-Joachim,Wolpert, Marcus
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p. 533 - 536
(2007/10/03)
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- 3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo or thiotrione herbicidal agents
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There is provided a 3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo or thiotrione compound having the structural formula I STR1 Further provided are a composition and a method comprising that compound for the control of undesirable plant s
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- Syntheses of Zindoxifene and Analogues by Titanium-Induced Oxo-Amide Coupling
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Highly reactive titanium on graphite is used to reductively cyclize electron-rich acylamino carbonyl compounds 7, 8, 12, 14, and 16 to the corresponding indole derivatives 9, 10, 13, 15, and 17.Compound 9b is a known precursor of the mammary tumor-inhibiting compound zindoxifene (2).The other products are new analogues of this anticancer drug, exhibiting the substitution pattern previously recognized to be essential for high pharmacological activity. - Key Words: Indoles, 2-aryl- / Titanium graphite / Zindoxifene / Tumor-growth inhibitors / Alkylidenation, intramolecular
- Fuerstner, Alois,Jumbam, Denis N.,Seidel, Guenter
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p. 1125 - 1130
(2007/10/02)
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- Preparation of Nitrobenzaldehydes and Nitrophenyl Ketones by Electrophilic Amination of Nitrobenzyl Aryl Sulfones
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Nitrobenzyl aryl sulfones 1a-g react with 3,3-pentamethylene-oxaziridine (2) with incorporation of an NH group into the benzylic position, followed by cleavage to nitrobenzaldehydes 4a-d and nitrophenyl ketones 4e-g, respectively.
- Wulf, Jens-Peter,Sienkiewicz, Krzysztof,Makosza, Mieczyslaw,Schmitz, Ernst
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p. 537 - 538
(2007/10/02)
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