- Excited State Intramolecular Proton Transfer (ESIPT)-Based Sensor for Ion Detection
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C-2 and C-5 substituted imidazole skeleton was synthesized through a one-pot two-step strategy. Synthesized molecule emits the light on ESIPT (excited-state intramolecular proton transfer). This molecule was utilized for its proton donor ability, and we have observed that fluoride and cyanide ions can be detected selectively. Different cations and anions were selected to observe the response of the synthesized molecule. However, there were not any fluorometric and colorimetric response except for fluoride and cyanide ions. Detection limits of fluoride and cyanide ions were found to be 9.22?μM and 11.48?μM, respectively. 1H-NMR spectra for the solution of the sensor and TBAF (tetrabuthylammoniumfluoride) were used for the identification of [L]?[HF2]? species. 3 equiv. TBAF saturated the solution of the sensor in d6-DMSO, and some of the proton resonances shifted to upfield due to the through-bond effect. The disappearance of NH proton with 0.5 equiv. TBAF or TBACN (tetrabuthylammoniumcyanide) showed that there was a proton abstraction by fluoride and cyanide ions, instead of the hydrogen bond. Solid-state application was utilized, and paper test strips were applied. Emission differences emerged when the sensor loaded strips were reacted with TBAF. Time resolved experiments revealed that solution of the sensor and TBAF in DMSO have multiexponential decay, and one of the lifetime was measured as 13.4?ns.
- Kuzu, Burak,Ekmekci, Zeynep,Tan, Meltem,Menges, Nurettin
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p. 861 - 872
(2021/04/05)
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- A novel class for carbonic anhydrases inhibitors and evaluation of their non-zinc binding
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In this study, 23 different imidazole derivatives were synthesized, and the inhibitory properties of these derivatives against carbonic anhydrase I and II isoenzymes were investigated for the first time. The inhibition concentrations of the imidazole derivatives were found to be in the range of 2.89–115.5 nM. Docking studies examined the binding properties of the imidazole derivatives, and the structure–activity relationship is discussed. Theoretical calculations showed that the binding mode of the imidazole ring was non-zinc binding.
- Kuzu, Burak,Tan, Meltem,Gül?in, ?lhami,Menges, Nurettin
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- Ynonylation of Acyl Radicals by Electroinduced Homolysis of 4-Acyl-1,4-dihydropyridines
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Herein we report the conversion of 4-Acyl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions. The reaction proceeds via the homolysis of acyl-DHP under electron activation. The resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This mild reaction condition allows wider functionality tolerance that includes halides, carboxylates, or alkenes. The synthetic utility of this methodology is further demonstrated by the late-stage modification of complex molecules.
- Luo, Xiaosheng,Wang, Ping
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supporting information
p. 4960 - 4965
(2021/07/20)
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- Catalytic Asymmetric Darzens-Type Epoxidation of Diazoesters: Highly Enantioselective Synthesis of Trisubstituted Epoxides
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Highly enantioselective Darzens-type epoxidation of diazoesters with glyoxal derivatives was accomplished using a chiral boron–Lewis acid catalyst, which facilitated asymmetric synthesis of trisubstituted α,β-epoxy esters. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99 %) with excellent enantio- and diastereoselectivity (up to >99 % ee and >20:1 dr, respectively). The synthetic potential of this method was illustrated by conversion of the products to various compounds such as epoxy γ-butyrolactone, tertiary β-hydroxy ketone and epoxy diester.
- Nam, Dong Guk,Shim, Su Yong,Jeong, Hye-Min,Ryu, Do Hyun
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supporting information
p. 22236 - 22240
(2021/09/13)
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- Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME
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Herein, we describe a visible light-promoted hydroacylation strategy that facilitates the preparation of ketones from alkenes and 4-acyl-1,4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives. In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence of NiCl2·DME.
- Zhao, Xinxin,Li, Bing,Xia, Wujiong
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supporting information
p. 1056 - 1061
(2020/02/15)
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- Synthesis and solid-state luminescence of highly-substituted 6-amino-2H-pyran-2-one derivatives
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A fast and convenient synthesis and solid-state luminescence properties of new highly-substituted 6-amino-2H-pyran-2-one derivatives is described. These compounds were obtained from inexpensive and available 2-acyl(aroyl)-1,3-dicyano-1,3-bis-methoxycarbonylpropenides via regioselective heterocyclization under the action of sulfuric and hydroiodic acid. Compounds containing 6-amino-2H-pyran-2-one moiety are nearly unstudied, but are of interest for obtaining condensed biologically active compounds based on this scaffold.
- Karpov, Sergey,Kayukov, Yakov,Grigor'ev, Arthur,Nasakin, Oleg,Kayukova, Olga,Tafeenko, Viktor
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- Antiproliferative Activity of 2-Aroyland 2-Heteroyl-1,1,3,3-Tetracyanoprop-2-en-1-ides
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The influence of previously synthesized 2-aroyl-1,1,3,3-tetracyanoprop-2-en-1-ides on the growth of conditionally normal and tumor cells was studied in continuation of a search for new anticancer drugs. Cytotoxicities of the compounds were studied with respect to human tumor cell lines from the ATCC. All compounds were ineffective against melanoma and lung and ovary cancer cell lines and exhibited moderate activity in the other cases. The tested compounds exhibited highly selective effects because they were safe for conditionally normal skin fibroblasts.
- Kayukov, Ya. S.,Mar’yasov, M. A.,Nasakin, O. E.
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-
- Asymmetric Conjugate Addition of α-Cyanoketones to Benzoyl Acrylonitrile Derivatives Using a Diaminomethylenemalononitrile Organocatalyst
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A diaminomethylenemalononitrile (DMM) organocatalyst was used to efficiently promote asymmetric conjugate addition of various α-cyanoketones to benzoyl acrylonitrile derivatives. The corresponding 1,5-dicarbonyl compounds containing vicinal tertiary and quaternary stereogenic centers are versatile synthetic intermediates and were obtained in good yields and with excellent enantioselectivities (up to 96% ee). The present study describes the first successful examples of asymmetric conjugate addition reactions of α-cyanoketones with benzoyl acrylonitriles. In addition, the DMM organocatalyst can be recovered and reused up to five times without significant loss of either catalytic activity or enantioselectivity.
- Akutsu, Hiroshi,Nakashima, Kosuke,Kanetsuna, Yuta,Kawada, Masahiro,Hirashima, Shin-Ichi,Miura, Tsuyoshi
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p. 3874 - 3880
(2020/10/06)
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- Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls
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2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.
- Dubovtsev, Alexey Yu.,Shcherbakov, Nikolay V.,Dar'in, Dmitry V.,Kukushkin, Vadim Yu.
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p. 745 - 757
(2020/02/04)
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- Mono- or di-substituted imidazole derivatives for inhibition of acetylcholine and butyrylcholine esterases
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Mono- or di-substituted imidazole derivatives were synthesized using a one-pot, two-step strategy. All imidazole derivatives were tested for AChE and BChE inhibition and showed nanomolar activity similar to that of the test compound donepezil and higher than that of tacrine. Structure activity relationship studies, docking studies to on X-ray crystal structure of AChE with PDB code 1B41, and adsorption, distribution, metabolism, and excretion (ADME) predictions were performed. The synthesized core skeleton was bound to important regions of the active site of AChE such as the peripheral anionic site (PAS), oxyanion hole (OH), and anionic subsite (AS). Selectivity of the reported test compounds was calculated and enzyme kinetic studies revealed that they behave as competitive inhibitors, while two of the test compounds showed noncompetitive inhibitory behavior. ADME predictions revealed that the synthesized molecules might pass through the blood brain barrier and intestinal epithelial barrier and circulate freely in the blood stream without binding to human serum albumin. While the toxicity of one compound on the WS1 (skin fibroblast) cell line was 1790 μM, its toxicity on the SH-SY5Y (neuroblastoma) cell line was 950 μM.
- Kuzu, Burak,Tan, Meltem,Taslimi, Parham,Gül?in, ?lhami,Ta?p?nar, Mehmet,Menges, Nurettin
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p. 187 - 196
(2019/02/06)
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- Oxidative C-C Bond Cleavage for the Synthesis of Aryl Carboxylic Acids from Aryl Alkyl Ketones
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A metal-free and one-pot two-step synthesis of aryl carboxylic acids from aryl alkyl ketones has been achieved. The reactions were performed with iodine as the catalyst, DMSO and TBHP as the oxidants. Under the optimal reaction conditions, a number of aryl alkyl ketones could be converted into their corresponding aryl carboxylic acids in good to excellent yields (up to 94%).
- Xu, Liang,Wang, Shengpeng,Chen, Bajin,Li, Meichao,Hu, Xinquan,Hu, Baoxiang,Jin, Liqun,Sun, Nan,Shen, Zhenlu
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supporting information
p. 1505 - 1509
(2018/05/25)
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- Synthesis of novel imidazopyridines and their biological evaluation as potent anticancer agents: A promising candidate for glioblastoma
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Novel imidazopyridine derivatives were synthesized according to a very simple protocol and then subjected to cytotoxicity testing against LN-405 cells. Two of the compounds exhibited antiproliferative effects on LN-405 cells at 10 and 75 μM and were selected as lead compounds for further study. Safety experiment for lead compounds on WS1 was carried out and IC50 values were calculated as 480 and 844 μM. LN-405 cell line were incubated with the lead compounds and then tested for DNA damage by comet assay and effects on cell cycle using flow cytometry. The results of these two tests showed that both lead compounds affected the G0/G1 phase and did not allow the cells to reach the synthesis phase. The log BB (blood–brain barrier) and Caco-2 permeability of the synthesized molecules were calculated and it was shown that imidazopyridine derivatives taken orally are likely to pass through gastrointestinal membrane and the blood–brain barrier.
- Gü?lü, Dilek,Kuzu, Burak,Tozlu, ?srafil,Ta?p?nar, Filiz,Canp?nar, Hande,Ta?p?nar, Mehmet,Menges, Nurettin
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supporting information
p. 2647 - 2651
(2018/07/06)
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- 9-Ethyl-3-{6-(het)aryl-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl}-9H-carbazoles: synthesis and study of sensitivity to nitroaromatic compounds
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5-(9-Ethyl-9H-carbazol-3-yl)-substituted 6-(het)aryl[1,2,5]oxadiazolo[3,4-b]pyrazines were synthesized by direct transition metal-free C—H functionalization in the pyrazine ring. Their photophysical and sensory properties with respect to nitrobenzene and
- Verbitskiy,Kvashnin, Yu. A.,Baranova,Yakovleva, Yu. A.,Khokhlov,Rusinov,Charushin
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p. 1078 - 1082
(2018/10/02)
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- Visible-light assisted one-pot preparation of aryl glyoxals from acetoarylones via in-situ arylacyl bromides formation: Selenium-free approach to acetoarylones oxidation
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A novel visible-light (blue LEDs: hν?=?425?±?15?nm) photocatalyzed one-pot method for the synthesis of electronically diverse aryl glyoxals in good to excellent yields from acetoarylones and green regents such as air, vitamin C and dioxane dibromide has been described. In addition, an application of the current methodology has been demonstrated for the oxidation of monoamine oxidase-B inhibitors, i.e., 1-(4-((4-fluorobenzyl)oxy)phenyl)ethanone and 1-(3-((4-chlorobenzyl)oxy)phenyl)ethanone. This finding may serves as a valuable alternative to the traditional acetoarylones oxidation reactions conducted using selenium dioxide a harmful and unselective reagent known to simultaneously oxidize allylic, benzylic, [sbnd]CH3and so on.
- Natarajan, Palani,Manjeet,Kumar, Naveen,Devi, Sapna,Mer, Kalyani
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supporting information
p. 658 - 662
(2017/01/25)
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- Synthesis of 2-acyl-benzo[1,3-d]selenazoles via domino oxidative cyclization of methyl ketones with bis(2-aminophenyl) diselenide
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A general, practical and simple one-pot synthesis of 2-acyl-benzo[1,3-d]selenazoles was developed by reacting a wide range of 2-arylethane-1,2-diones, generated in situ from commercially available aryl methyl ketones, with bis(2-aminophenyl) diselenide, promoted by Na2S2O5 in DMSO at 100 °C. Comparatively, the reactions were conducted under conventional heating and microwave irradiation. The use of focused microwave irradiation drastically decreased the reaction time from 48 to 2 h with a gain in the reaction yield for most cases. Still, 2-phenylacyl-benzo[1,3-d]selenazole was elected to react with sodium borohydride and butylmagnesium bromide, giving the respective secondary and tertiary alcohols under mild reaction conditions.
- Balaguez, Renata A.,Betin, Eduardo S.,Barcellos, Thiago,Lenard?o, Eder J.,Alves, Diego,Schumacher, Ricardo F.
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supporting information
p. 1483 - 1487
(2017/02/23)
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- Experimental and Theoretical Studies on Iron-Promoted Oxidative Annulation of Arylglyoxal with Alkyne: Unusual Addition and Migration on the Aryl Ring
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An Fe(III)-promoted oxidative annulation reaction was developed for the synthesis of 1,2-naphthoquinones. A variety of substituted arylglyoxals and internal alkynes undergo the transformation in the presence of FeCl3 at room temperature to afford the 1,2-naphthoquinone products in good yields in a short reaction time. Interestingly, the products show unusual pseudomigration of the substituent on the arene ring of arylglyoxals. A possible mechanism involving Fe(III)-promoted formation of a vinyl cation from arylglyoxal and alkyne, electrophilic addition of the vinyl cation to the ipso carbon of the aryl group to give a spiral intermediate, and then migration of the keto carbon to the ortho carbon was proposed as key steps and verified using quantum mechanics.
- Hung, Chen-Hsun,Gandeepan, Parthasarathy,Cheng, Lin-Chieh,Chen, Liang-Yu,Cheng, Mu-Jeng,Cheng, Chien-Hong
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supporting information
p. 17015 - 17021
(2017/12/06)
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- Synthesis and X-ray Characterization of Alkali Metal 2-Acyl-1,1,3,3-tetracyanopropenides
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A novel route for synthesis of 2-acyl-1,1,3,3-tetracyanopropenides (ATCN) salts in high yields and excellent purities starting from readily available methyl ketones, malononitrile, bromine, and alkali metal acetates is reported. The starting aryl(heteroaryl) methyl ketones were oxidized to the corresponding α-ketoaldehydes by new a DMSO-NaBr-H2SO4 oxidation system in yields up to 90% within a short reaction time of 8-10 min. The subsequent stages of ATCN preparation are realized in aqueous media without use of any toxic solvents, in accordance with principle 5 of "green chemistry". Lithium, sodium, potassium, rubidium, and cesium 2-benzoyl-1,1,3,3-tetracyanopropenides were characterized by X-ray diffraction analysis. These salts show a good potential for synthesis of five- and six-membered heterocycles and may serve as potentially useful ligands in coordination and supramolecular chemistry.
- Karpov, Sergey V.,Grigor'Ev, Arthur A.,Kayukov, Yakov S.,Karpova, Irina V.,Nasakin, Oleg E.,Tafeenko, Victor A.
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p. 6402 - 6408
(2016/08/16)
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- One-pot three-component reactions of methyl ketones, phenols and a nucleophile: An expedient way to synthesize densely substituted benzofurans
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Three-component reactions of phenylglyoxal monohydrate, phenols, and indoles were developed with the aid of acid-catalyst, which produced various densely substituted benzofurans with good to excellent yields. On the basis of this observation, a one-pot, step-wise reaction was developed by using methyl ketones instead of using phenylglyoxal component in I2/DMSO system. At last, three-component reaction offered a useful way to synthesize densely substituted benzofurans starting from simple and easily available substrates. The indole component can be replaced by some other nucleophiles, such as 1,2,4-trimethoxybenzene and thiophenol.
- Cheng, Cheng,Liu, Changhui,Gu, Yanlong
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p. 8009 - 8017
(2015/12/31)
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- Synthesis of 2-aroyl-(4 or 5)-aryl-1H-imidazoles and 2-hydroxy-3,6-diaryl- pyrazines via a cascade process
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The synthesis of (4 or 5)-aryl-2-aroyl-1H-imidazoles and 2-hydroxy-3,6-diarylpyrazines from aryl methyl ketones via a cascade process of DMSO-HBr oxidation and Debus reaction was investigated. Owing to the simple starting materials, mild conditions, easy operation, high bioactivity of imidazole and pyrazine derivatives, this protocol has great potential in medicinal chemistry.
- Liu, Cong,Dai, Rong J.,Yao, Guo W.,Deng, Yu L.
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p. 146 - 163
(2014/04/17)
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- Iodine-mediated oxidative annulation for one-pot synthesis of pyrazines and quinoxalines using a multipathway coupled domino strategy
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An efficient iodine-mediated oxidative annulation of aryl acetylenes-arylethenes-aromatic ketones with 1,2-diamines for the synthesis of pyrazines and regioselective synthesis of quinoxalines is presented. A multipathway coupled domino approach has been developed for the one-pot synthesis of 1,4-diazines with high functional group compatibility.
- Viswanadham, K. K. Durga Rao,Prathap Reddy, Muktapuram,Sathyanarayana, Pochampalli,Ravi, Owk,Kant, Ruchir,Bathula, Surendar Reddy
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supporting information
p. 13517 - 13520
(2015/01/09)
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- Antimicrobial relevance of Cu(II) complexes of thiophene-2-glyoxal-p-halogen substituted anils
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Isomeric complexes of, p-chloro, p-bromo, and p-iodo-anils of 2-thiophene glyoxal ligands have been synthesized and characterized by metal analysis, molecular weight, infrared and UV-Visible spectroscopy, molar conductance and magnetic measurements. All n
- Adamu, Fentahun,Upadhyay, Sanidhya,Upadhyay
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p. 1031 - 1036
(2015/02/19)
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- [1,2,4]TRIAZOLO[4,3-B][1,2,4]TRIAZINE COMPOUND, PREPARATION METHOD AND USE THEREOF
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The present invention relates to a structurally novel [1,2,4]triazolo[4,3-b][1,2,4]triazine compounds represented by formula (I) or formula (II), pharmaceutically acceptable salts thereof, prodrugs thereof, hydrates or solvates thereof, and also relates to a preparation method of the compounds, a pharmaceutical composition comprising a therapeutically effective amount of the compounds, as well as the use thereof as protein tyrosine kinase inhibitors, particularly as c-Met inhibitors, in the preparation of medicaments for the prevention and/or treatment of diseases associated with c-Met abnormality.
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-
Paragraph 0046; 0047
(2013/11/05)
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- Oxidation of aryl and heteroaryl methyl ketone to aryl and heteroarylglyoxals by using CuCl2-DMSO
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The oxidation of aryl methyl ketone and heteroaryl methyl ketone to arylglyoxals and heteroaryl glyoxal respectively has been carried out by using the cheap and easily available, non toxic, Lewis acid CuCl2 in DMSO solvent at 70-80°C within 1-2 hr. The reaction can be performed in air without loss of variety of oxidisable fuctional group like phenolic OH, hetroaryl ring, aryl substituted methyl, halo, nitro group, etc.
- Lokhande, Pradeep D.,Waghmare, Smita R.,Gaikwad, Harsh,Hankare
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p. 300 - 305
(2013/05/08)
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- Design and synthesis of 2-acylbenzothiazoles via in situ cross-trapping strategy from benzothiazoles with aryl ketones
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An I2/KOH synergistically promoted direct ring-opening aroylation of benzothiazoles with aryl ketones has been discovered. Aryl ketones were seen to act as carbonyl sources to construct 2-acylbenzothiazoles. This reaction could provide an example for the convergent integration of self-labor domino sequences based on an in situ cross-trapping strategy.
- Gao, Qinghe,Wu, Xia,Jia, Fengcheng,Liu, Meicai,Zhu, Yanping,Cai, Qun,Wu, Anxin
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p. 2792 - 2797
(2013/04/24)
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- Synthesis and anti-protozoal activity of C2-substituted polyazamacrocycles
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A focused library of C2-substituted-1,4,7,10-tetraazacyclododecanes was synthesised and the compounds were tested for their ability to kill trypanosome and malaria parasites. Several compounds showed significant in vitro activity and were selectively active against the parasites over human embryonic kidney cells used as a counter screen.
- Reid, Caroline M.,Ebikeme, Charles,Barrett, Michael P.,Patzewitz, Eva-Maria,Mueller, Sylke,Robins, David J.,Sutherland, Andrew
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p. 2455 - 2458
(2008/09/21)
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- NOVEL TYROSINASE INHIBITORS, THEIR PROCESS OF PREPARATION AND THEIR USE IN HUMAN MEDICINE AND IN COSMETICS
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The present invention relates to the use of compounds corresponding to the following general formula (I) in pharmaceutical compositions intended for use in human or veterinary medicine or else in cosmetic compositions, and also to novel compounds of formula (II) and to the compositions comprising them.
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Page/Page column 29
(2008/06/13)
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- Reactions of lithiated aromatic heterocycles with carbon monoxide
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The reaction of lithium derivatives of aromatic heterocycles with carbon monoxide was studied under several reaction conditions: 2-furyllithium afforded only one product, the tetrahydro-2-furaldehyde (25% yield). On the other hand, 2-thienyllithium and 5-methyl-2-furyllithium gave two and five products, respectively. Although in relatively low yields, formation of highly functionalized compounds takes place in a fast process under mild conditions. For 1,4-dihydroxy-1,4-bis(5-methyl-2-furanyl)butane-2,3-dione, reaction conditions were achieved to obtain this difficult to prepare derivative in 50% yield. To the best of our knowledge, this is the first report on the reaction of lithiated aromatic heterocycles with CO: evidence is given on the involvement of proton transfers in the reactions of 2-furyllithium and 2-thienyllithium, while the reaction of 5-methyl-2-furyllithium seems to proceed through an electron transfer as the first step. Copyright
- Garcia Linares, Guadalupe E.,Nudelman, Norma S.
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p. 569 - 576
(2007/10/03)
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- 7-(substituted)piperazinyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids
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7-(substituted)piperazinyl-1-ethyl-6-fluoro-4-oxo-3-quinolinecarboxylic acids, the pharmacologically acceptable salts thereof, compositions containing them, processes and intermediates for producing them, and methods of using them to treat bacterial infections in warm-blooded animals.
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- 6-(1-ACYL-1-HYDROXYMETHYL)PENICILLANIC ACID DERIVATIVES
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6-(1-Acyl-1-hydroxymethyl)penicillanic acid derivatives are useful as antibacterials and/or beta-lactamase inhibitors.
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- Structure-activity Relationship of Herbicidal 2,3-Dicyano-5-Substituted Pyrazines
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Sixty six 2,3-dicyano-5-substituted pyrazines were synthesized and their herbicidal activities against barnyard grass were measured in pot tests to clarify the relationship between chemical structure and activity.The activity of 59 derivatives was related parabolically to the hydrophobic substituent parameter at the 5-position of the pyrazine ring.
- Nakamura, Akira,Ataka, Toshiei,Segawa, Hirozo,Takeuchi, Yasutomo,Takematsu, Tetsuo
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p. 1555 - 1560
(2007/10/02)
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