- N-(2-hydroxy-5-chlorophenyl)thiophenyl-acetamide
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In molecules of the title compound, C14H12ClNO2S, the phenylthio group and the remainder of the heavyatom skeleton form two different planes which are nearly perpendicular to each other. The molecules are interlinked by O-
- Tarimci, Celik,Ercan, Filiz,Kocoglu, Meltem,Oeren, Ilkay
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- Synthesis of and characterization of some Heterocyclic Compounds derived from Thiophenol
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This research work involved preparation of heterogeneous pent lateral cyclic compounds (thiazolidine -4- one, benzothiazole, triazole, 4-oxothiazolidin) using thiophenol as raw materials: Thiophenol was reacted with mono chloroacetic acid in the presence of potassium hydroxide to prepare (sh1) followed by ortho amino aniline results the (sh2). The reaction of thiophenol with ethylchloroacetate afforded (sh3) and the reaction of (sh3) with thiosemicarbazide and 4% NaOH leads to ring closure giving 1,2,4- triazole (sh5). A treatment of thiophenol with hydrazine hydrate to obtain the intermediate (sh6) with aromatic aldehyde synthesized azomethines (sh7- sh9) then treated with mercaptoacetic acid to obtained (sh10-sh12). A treatment of thiophenol with chloroacetyl chloride produced (sh13) compound then treated with hydrazine hydrate to obtain (sh14) compound followed by bromobenzaldehyde synthesized azomethine (sh15) compound then treated with mercaptoacetic acid to obtained (sh16) compound. Characterization results for the prepared compounds using IR spectroscopy, NMR and melting points confirmed their chemical structures.
- AL-Khazraji, Shaima Ibraheem Chyad
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p. 5655 - 5662
(2021/09/11)
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- Design, Synthesis, and Antifungal Evaluation of Cryptolepine Derivatives against Phytopathogenic Fungi
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Inspired by the widely antiphytopathogenic application of diversified derivatives from natural sources, cryptolepine and its derivatives were subsequently designed, synthesized, and evaluated for their antifungal activities against four agriculturally important fungi Rhizoctonia solani, Botrytis cinerea, Fusarium graminearum, and Sclerotinia sclerotiorum. The results obtained from in vitro assay indicated that compounds a1-a24 showed great fungicidal property against B. cinerea (EC50 4 μg/mL); especially, a3 presented significantly prominent inhibitory activity with an EC50 of 0.027 μg/mL. In the pursuit of further expanding the antifungal spectrum of cryptolepine, ring-opened compound f1 produced better activity with an EC50 of 3.632 μg/mL against R. solani and an EC50 of 5.599 μg/mL against F. graminearum. Furthermore, a3 was selected to be a candidate to investigate its preliminary antifungal mechanism to B. cinerea, revealing that not only spore germination was effectively inhibited and the normal physiological structure of mycelium was severely undermined but also detrimental reactive oxygen was obviously accumulated and the normal function of the nucleus was fairly disordered. Besides, in vivo curative experiment against B. cinerea found that the therapeutic action of a3 was comparable to that of the positive control azoxystrobin. These results suggested that compound a3 could be regarded as a novel and promising agent against B. cinerea for its valuable potency.
- Chen, Yong-Jia,Liu, Hua,Zhang, Shao-Yong,Li, Hu,Ma, Kun-Yuan,Liu, Ying-Qian,Yin, Xiao-Dan,Zhou, Rui,Yan, Yin-Fang,Wang, Ren-Xuan,He, Ying-Hui,Chu, Qing-Ru,Tang, Chen
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p. 1259 - 1271
(2021/02/16)
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- Rhodium-catalyzed Sommelet-Hauser type rearrangement of α-diazoimines: Synthesis of functionalized enamides
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An efficient rhodium catalyzed Sommelet-Hauser type rearrangement of sulfur ylides derived from α-thioesters and N-sulfonyl-1,2,3-triazoles has been successfully accomplished for the synthesis of various functionalized enamides. The developed reaction involves the unprecedented [2,3]-sigmatropic rearrangement of sulfur ylides with the imine motif. Importantly, the method works well with various substituted α-thioesters/-amides/-ketones and substituted N-sulfonyl-1,2,3-triazoles and allows the synthesis of diverse enamide derivatives in good to excellent yields. The reaction was also successfully extended to the one-pot synthesis of enamides from terminal alkynes.
- Anbarasan, Pazhamalai,Ramachandran, Kuppan,Reddy, Angula Chandra Shekar,Reddy, Palagulla Maheswar
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p. 5649 - 5652
(2020/06/09)
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- Oxidized Hemithioindigo Photoswitches—Influence of Oxidation State on (Photo)physical and Photochemical Properties
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The photophysical and photochemical properties of sulfoxide and sulfone derivatives of hemithioindigo photoswitches are scrutinized and compared to the unoxidized parent chromophores. Oxidation results in significantly blue-shifted absorptions and mostly
- K?ttner, Laura,Schildhauer, Monika,Wiedbrauk, Sandra,Mayer, Peter,Dube, Henry
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supporting information
p. 10712 - 10718
(2020/07/27)
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- Synthesis of novel 1,2,5-oxadiazoles and evaluation of action against Acinetobacter baumannii
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With multidrug resistant bacteria on the rise, novel antibiotics are becoming highly sought after. In 2008, eleven compounds were identified by high throughput screening as inhibitors of BasE, a key enzyme of the non-ribosomal peptide synthetase pathway found in Acinetobacter baumannii. Herein, we describe the preparation of four structurally similar heterocyclic lead compounds from that study, including one 1,2,5-oxadiazole. A further library of 30 analogues containing the oxadiazole moiety was then generated. All compounds were screened against Acinetobacter baumannii and their minimum inhibitory concentration data is reported, with (E)-3-(2-hydroxyphenyl)-N-(4-methyl-1,2,5-oxadiazol-3-yl)acrylamide 32 found to have an MIC of 0.5 mM. This work provides the foundation for further investigation of 1,2,5-oxadizoles as novel inhibitors of A. baumannii.
- Christoff, Rebecca M.,Murray, Gerald L.,Kostoulias, Xenia P.,Peleg, Anton Y.,Abbott, Belinda M.
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supporting information
p. 6267 - 6272
(2017/10/13)
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- Thioester-appended organosilatranes: Synthetic investigations and application in the modification of magnetic silica surfaces
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The present investigation discloses a series of new organosilicon derivatives (3a-k) tailored with substituted benzoic acid modules (1a-k) via thioesterification with 3-mercaptopropylsilatrane (MPS). Product formation was authenticated using elemental analyses and different spectroscopic methods comprising FT-IR, NMR [1H, 13C] and LC-MS (Q-TOF). Thereafter, complete structural elucidation of compounds 3c and 3f was achieved by the single crystal X-ray technique. Photo-electronic inspection of all compounds by UV-Vis spectroscopy revealed their sensitivity towards substitution patterns. In addition, this is the first time that the potential of a silatranyl moiety has been tested for the modification of a silica surface pre-decorated with a magnetite core. The synthesis was achieved through a facile methodology involving chemical bonding at each stage, which proceeded without any external surfactant or template. The course of the reaction was followed by FT-IR, UV-Vis, XRD, TEM, FESEM, EDX and TGA techniques. Furthermore, the hybrid nanomaterial possessed significant sensorial ability toward copper ions, which makes the present protocol favourable for the construction of a new class of chelating ligands with an in-built multifunctional nanodevice.
- Singh, Gurjaspreet,Rani, Sunita,Arora, Aanchal,Aulakh, Darpandeep,Wriedt, Mario
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p. 6200 - 6213
(2016/07/19)
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- HYDROXAMIC ACID DERIVATIVES AND HDAC8 INHIBITORS
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PROBLEM TO BE SOLVED: To provide compounds that are highly active and can highly selectively inhibit HDAC8 functionality, and HDAC8 inhibitors. SOLUTION: Each hydroxamic acid derivative comprise a compound of the general formula (1) in the figure, where φ
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Paragraph 0025; 0028
(2016/10/07)
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- Twisted Hemithioindigo Photoswitches: Solvent Polarity Determines the Type of Light-Induced Rotations
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Controlling the internal motions of molecules by outside stimuli is a decisive task for the generation of responsive and complex molecular behavior and functionality. Light-induced structural changes of photoswitches are of special high interest due to the ease of signal application and high repeatability. Typically photoswitches use one reaction coordinate in their switching process and change between two more or less-defined states. Here we report on new twisted hemithioindigo photoswitches enabling two different reaction coordinates to be used for the switching process. Depending on the polarity of the solvent, either complete single bond (in DMSO) or double bond (in cyclohexane) rotation can be induced by visible light. This mutually independent switching establishes an unprecedented two-dimensional control of intramolecular rotations in this class of photoswitches. The mechanistic explanation involves formation of highly polar twisted intramolecular charge-transfer species in the excited state and is based on a large body of experimental quantifications, most notably ultrafast spectroscopy and quantum yield measurements in solvents of different polarity. The concept of pre-twisting in the ground state to open new, independent reaction coordinates in the excited state should be transferable to other photoswitching systems.
- Wiedbrauk, Sandra,Maerz, Benjamin,Samoylova, Elena,Reiner, Anne,Trommer, Florian,Mayer, Peter,Zinth, Wolfgang,Dube, Henry
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supporting information
p. 12219 - 12227
(2016/10/03)
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- Development of Chiral Spiro P-N-S Ligands for Iridium-Catalyzed Asymmetric Hydrogenation of β-Alkyl-β-Ketoesters
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The chiral tridentate spiro P-N-S ligands (SpiroSAP) were developed, and their iridium complexes were prepared. Introduction of a 1,3-dithiane moiety into the ligand resulted in a highly efficient chiral iridium catalyst for asymmetric hydrogenation of β-alkyl-β-ketoesters, producing chiral β-alkyl-β-hydroxyesters with excellent enantioselectivities (95-99.9 % ee) and turnover numbers of up to 355 000. Bulkyness is the key: New chiral tridentate spiro P-N-S ligands (SpiroSAP) bearing a conformationally constrained 1,3-dithiane moiety were developed. Their iridium catalysts showed excellent enantioselectivities and activity (TON up to 355 000) for asymmetric hydrogenation of β-alkyl-β-ketoesters.
- Bao, Deng-Hui,Wu, Hui-Ling,Liu, Chao-Lun,Xie, Jian-Hua,Zhou, Qi-Lin
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supporting information
p. 8791 - 8794
(2015/11/27)
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- Design, synthesis, and biological activity of NCC149 derivatives as histone deacetylasea 8-selective inhibitors
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We recently discovered N-hydroxy-3-[1-(phenylthio)methyl-1H-1,2,3-triazol- 4-yl]benzamide (NCC149) as a potent and selective histone deacetylasea 8 (HDAC8) inhibitor from a 151-member triazole compound library using a click chemistry approach. In this wor
- Suzuki, Takayoshi,Muto, Nobusuke,Bando, Masashige,Itoh, Yukihiro,Masaki, Ayako,Ri, Masaki,Ota, Yosuke,Nakagawa, Hidehiko,Iida, Shinsuke,Shirahige, Katsuhiko,Miyata, Naoki
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p. 657 - 664
(2014/03/21)
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- Synthesis, biological evaluation, and structure-activity relationships of potent noncovalent and nonpeptidic cruzain inhibitors as anti-Trypanosoma cruzi agents
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The development of cruzain inhibitors has been driven by the urgent need to develop novel and more effective drugs for the treatment of Chagas' disease. Herein, we report the lead optimization of a class of noncovalent cruzain inhibitors, starting from an inhibitor previously cocrystallized with the enzyme (Ki = 0.8 μM). With the goal of achieving a better understanding of the structure-activity relationships, we have synthesized and evaluated a series of over 40 analogues, leading to the development of a very promising competitive inhibitor (8r, IC50 = 200 nM, Ki = 82 nM). Investigation of the in vitro trypanocidal activity and preliminary cytotoxicity revealed the potential of the most potent cruzain inhibitors in guiding further medicinal chemistry efforts to develop drug candidates for Chagas' disease.
- Ferreira, Rafaela S.,Dessoy, Marco A.,Pauli, Ivani,Souza, Mariana L.,Krogh, Renata,Sales, Ana I. L.,Oliva, Glaucius,Dias, Luiz C.,Andricopulo, Adriano D.
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supporting information
p. 2380 - 2392
(2014/04/17)
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- Making fast photoswitches faster - Using hammett analysis to understand the limit of donor-acceptor approaches for faster hemithioindigo photoswitches
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Hemithioindigo (HTI) photoswitches have a tremendous potential for biological and supramolecular applications due to their absorptions in the visible-light region in conjunction with ultrafast photoisomerization and high thermal bistability. Rational tail
- Maerz, Benjamin,Wiedbrauk, Sandra,Oesterling, Sven,Samoylova, Elena,Nenov, Artur,Mayer, Peter,De Vivie-Riedle, Regina,Zinth, Wolfgang,Dube, Henry
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supporting information
p. 13984 - 13992
(2016/02/18)
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- One-pot synthesis of 2-substituted benzoxazoles directly from carboxylic acids
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Methanesulfonic acid has been found to be a highly effective catalyst for a convenient and one-pot synthesis of 2-substituted benzoxazoles by the reaction of 2-aminophenol with acid chlorides, generated in situ from carboxylic acids. Aryl, heteroaryl, and arylalkyl carboxylic acids provided excellent yields of the corresponding benzoxazoles. The reaction conditions were compatible with various substituents such as chloro, bromo, nitro, methoxy, cyclopentyloxy, phenoxy, thiophenoxy, and conjugated double bonds. Benzoxazole formation was found to be general with respect to substituted 2-aminophenols.
- Kumar, Dinesh,Rudrawar, Santosh,Chakraborti, Asit K.
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scheme or table
p. 881 - 887
(2009/04/11)
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- Synthesis and in vitro antimicrobial activity of new 2-[p-substituted-benzyl]-5-[substituted-carbonylamino]benzoxazoles
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Some new 2-(benzyl/p-chlorobenzyl)-5-[(substituted-thienyl/phenyl/phenylthiomethyl/benzyl)carbonylamino]benzoxazole derivatives have been synthesized by reacting 5-amino-2-(benzyl/p-chlorobenzyl)benzoxazoles with appropriate carboxylic acid chlorides. The structures of the synthesized compounds were confirmed by IR, 1H NMR and MASS spectral data. In vitro antimicrobial activities of the compounds were investigated using twofold serial dilution technique against different two Gram-positive, two Gram-negative bacteria and three Candida spp. in comparison with standard drugs. Microbiological results indicated that the newly synthesized 2-(benzyl/p-chlorobenzyl)-5-[(substituted-thienyl/phenyl/phenylthiomethyl/benzyl)carbonylamino]benzoxazole derivatives (3-12) possessed a broad spectrum of activity having MIC values of 6.25-100 μg/ml against the tested microorganisms. Especially, with an MIC value of 6.25 μg/ml, 2-(p-chlorophenyl)-5-[(2,5-dimethylphenyl)carbonylamino]benzoxazole 4 displayed the same activity against Candida albicans as the standard drug clotrimazole.
- Tekiner-Gulbas, Betul,Temiz-Arpaci, Ozlem,Yildiz, Ilkay,Altanlar, Nurten
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p. 1293 - 1299
(2008/03/28)
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- Stereoselective synthesis of 2,4-disubstituted butanolides
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A series of 2,4-disubstituted butanolides was prepared based on the trans-stereoselective electrophilic cyclization of substituted N-(pent-4-enoyl)pyrrolidines. The butanolides may be considered as synthons for this type of natural products. Springer Scie
- Lozanova,Ugurchieva,Veselovsky
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p. 130 - 136
(2008/02/08)
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- The reactivity of N,N-dialkyl-N-(3-phenylsulfinyltetrahydrofuran-2-ylidene) ammonium bromide
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trans-Stereoselective electrophilic cyclization of (2Rz.ast;,SSz.ast;)-N, N-diisopropyl-2-phenylsulfinylpent-4-enamide under the action of bromine afforded (3Rz.ast;,5Sz.ast;, SSz.ast;)-N-(5-bromomethyl-3- phenylsulfinyltetrahydrofuran-2-ylidene)-N,N-diisopropylammonium bromide. Its transformations under the conditions of hydrolysis, dehydrobromination, and hydride reduction were studied.
- Ugurchieva,Lozanova,Zlokazov,Veselovsky
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p. 1544 - 1549
(2008/09/18)
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- Synthesis and antimicrobial activity of some novel 2-(p-substituted-phenyl)-5-substituted-carbonylaminobenzoxazoles.
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A series of 2-(p-substituted-phenyl)-5-substituted-carbonylamino benzoxazole derivatives (5-22) was synthesized and their antimicrobial activities determined in comparison to several control drugs. The synthesized compounds were tested in vitro against Staphylococcus aureus, Streptococcus faecalis and Bacillus subtilis as Gram-positive, Pseudomonas aeruginosa and Escherichia coli as Gram-negative bacteria and the yeast Candida albicans. Microbiological results showed that the compounds possessed a diffuse spectrum of antibacterial activity against these microorganisms. Compound 9 which bears a phenylacetamido moiety at position 5 and a 4-fluorophenyl group at the 2-position of benzoxazole ring was the most active derivative against S. aureus, S. faecalis and P. aeruginosa with a MIC value of 12.5 microg/ml. Compound 11 provided higher potency than the other tested compounds against B. subtilis at a MIC value of 12.5 microg/ml. Compounds 5-22 showed antifungal activity against C. albicans with MIC values between 50 and 12.5 microg/ml.
- Arpaci, Ozlem Temiz,Oren, Ilkay,Altanlar, Nurten
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p. 175 - 181
(2007/10/03)
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- 2-(4-R-Phenoxy/phenylthio)alkanoic esters of l-lupinine
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Considering the great pharmacological interest in phenoxy/phenylthioalkanoic esters of open-chain or cyclic aminoalcohols, a set of ten such esters of lupinine was prepared. Initially, their ability to displace [3H]QNB from rat brain preparation was investigated. With the exception of two, all the prepared esters exhibited good affinity to muscarinic receptors (on a non-selective basis), with pKi in the range 6.67-7.68.
- Sparatore, Anna,Sparatore, Fabio
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p. 169 - 174
(2007/10/03)
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- Intramolecular capture of pummerer reaction intermediates by an aromatic nucleophile: Selective construction of 1,4-benzothiazine and indole ring systems
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The simple alkyl sulfoxide 6 carrying two aromatic nucleophiles, when treated with trifluoroacetic anhydride at room temperature (Pummerer reaction conditions), underwent an intramolecular aromatic sulfenylation of the 6-exo-tet process in an exclusive ma
- Horiguchi,Sonobe,Saitoh,Toda,Sano
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p. 1132 - 1137
(2007/10/03)
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- Substituent-dictated partitioning of intermediates on the sulfide singlet oxygen reaction surface. A new mechanism for oxidative C-S bond cleavage in α-hydroperoxy sulfides
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The reactions of singlet oxygen with 17 sulfides bearing either anion or radical stabilizing substituents are reported. The abilities of substituents to modify product compositions in both the oxidative cleavage and sulfide oxidation pathways are analyzed in terms of partitioning of the hydroperoxy sulfonium ylide intermediate. Evidence is presented that suggests that the hydroperoxy sulfonium ylide exists in both diradical and zwitterionic forms. In addition, both inter- and intramolecular pathways for decomposition of α-hydroperoxy sulfides are suggested to rationalize the substituent-dependent formation of oxidative C-S bond cleavage products.
- Toutchkine,Aebisher,Clennan
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p. 4966 - 4973
(2007/10/03)
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- studies on anti-helicobacter pylori agents. Part 2: New cephem derivatives
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The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of cephem derivatives are described. Introduction of thio-heterocyclic groups containing N- and S-atoms to the 3-position and phenyl or thienyl acetamido groups to the 7-position of the cephem nucleus dramatically improved the activity. From this series of derivatives, compound 13i was found to have extremely potent in vitro anti-H. pylori activity, superior therapeutic efficacy compared to AMPC and CAM, no cross-resistance between CAM or MNZ and low potential for causing diarrhea due to instability to β-lactamase. Copyright (C) 2000 Elsevier Science Ltd.
- Yoshida, Yoshiki,Matsuda, Keiji,Sasaki, Hiroshi,Matsumoto, Yoshimi,Matsumoto, Satoru,Tawara, Shuichi,Takasugi, Hisashi
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p. 2317 - 2335
(2007/10/03)
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- A convenient synthesis of 3-phenylthio-azetidin-2-ones
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3-Phenylthio-4,4-diethoxycarbonyl-azetidin-2-ones 8 have been conveniently synthesised by reacting 2-chlorophenylthioacetyl chloride 5 with aryl substituted aminomalonates 7 under mild basic conditions. Alternatively, C-3 alkylation of azetidin-2-one usin
- Bari,Sharma,Sethi
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p. 1114 - 1119
(2007/10/03)
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- Synthesis and microbiological activity of some novel N-(2-hydroxyl-5- substitutedphenyl)benzacetamides, phenoxyacetamides and thiophenoxyacetamides as the possible metabolites of antimicrobial active benzoxazoles
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Synthesis of some novel N-(2-hydroxyl-5- substitutedphenyl)benzacetamides, phenoxyacetamides and thiophenoxyacetamides (5a-k) were described in order to determine their in vitro antimicrobial activity against 3 Gram-positive, 3 Gram-negative bacteria and the fungus Candida albicans comparing with several control drugs. The derivative 5e was found active at a MIC value of 25μg/ml against the whole tested Gram- positive bacteria strains and the Gram-negative microorganism Klebsiella pneumoniae. Moreover, the synthesized compounds 5a-k exhibited significant antibacterial activity against the enterobacter Pseudomonas aureginosae when compared to the control drugs. For the antifungal activity against C. albicans, the compound 5k was found more active than the other synthesized derivatives. On the other hand, the antimicrobial activity of some of these acetamide derivatives (5c, 5d, 5e, 5j and 5k) which are the possible metabolites of benzoxazoles, were also compared with their cyclic analogues 6-10. However, most of the MIC values of the benzoaxazole derivatives provided better activity than the compared acetamides, while some others of the acetamide derivatives possessed either one fold improved (5d, 5e and 5j) or the same potency (5c, 5d, 5e, 5j and 5k) against the tested microorganisms.
- Yalcin,Kaymakcioglu,Oren,Sener,Temiz
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p. 685 - 689
(2007/10/03)
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- Structure-activity relationship within a series of pyrazolidinone antibacterial agents. 2. Effect of side-chain modification on in vitro activity and pharmacokinetic parameters
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The structure-activity relationship among a series of novel pyrazolidinone antibacterial agents is described. Specifically, the effect of modification of the side chain attached to the nitrogen at C-7 was explored in an attempt to improve the potency and spectrum of activity. This approach was successful in identifying several compounds having good in vitro profiles. These top candidates were then evaluated for their activity in vivo, and their pharmacokinetic behavior in various animal models was explored. This information proved critical for the identification of candidates for clinical evaluation.
- Ternansky,Draheim,Pike,Counter,Eudaly,Kasher
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p. 3224 - 3229
(2007/10/02)
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- Synthesis of a Novel Tetracyclic Acridine. A Sulphoxide-based Route to the 1,2,3,4-Tetrahydrobenzophenanthroline Ring System
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The ambit of the classical acridine synthesis, via acid-mediated cyclisation of 2-oxodiphenylamines, has been extended to include a sulphoxide-containing precursor.This adaption produced the tetracyclic system of 1 in a single step from 25.
- Kennedy, Michael G.,Moody, Christopher J.,Rees, Charles W.,Thomas, Robert
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p. 2499 - 2504
(2007/10/02)
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- A CONVENIENT GENERAL ACCESS TO α-SULFENYLATED ACETOPHENONES AND ALKANONES
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Friedel-Crafts acylation of arenes with methylthio- (1) or phenylthio-acetyl chloride (2) provides ready access to α-methylthio- or α-phenylthio-substituted acetophenones.The acyl chlorides 1 and 2 reacted also with organoaluminium reagents to give α-sulfenylated alkanones.
- Ishibashi, Hiroyuki,Takamuro, Iwao,Mizukami, Yo-ichi,Irie, Maki,Ikeda, Masazumi
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p. 443 - 452
(2007/10/02)
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- AN APPROACH TO BUFADIENOLIDES FROM DEOXYCHOLIC ACID -1. STRATEGY AND SYNTHESIS OF A MODEL BUFADIENOLIDE
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A new procedure for the conversion of deoxycholic acid (14) to bufadienolde 27 is reported.
- Hoppe, Hans Wolfgang,Kaiser, Manfred,Mueller, Dietrich,Welzel, Peter
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p. 2045 - 2058
(2007/10/02)
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