cas 580-18-7, 3-Hydroxyquinoline | Articles data

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Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols
A V2O5@TiO2 catalyzed green and efficient protocol for the hydroxylation of boronic acid into phenol has been developed utilizing environmentally benign oxidant hydrogen peroxide. A wide range of electron-donating and the electron-withdrawing group-containing (hetero)aryl boronic acids were transformed into their corresponding phenol. The methodology was also applied successfully to transform various natural and bioactive molecules like tocopherol, amino acids, cinchonidine, vasicinone, menthol, and pharmaceuticals such as ciprofloxacin, ibuprofen, and paracetamol. The other feature of the methodology includes gram-scale synthetic applicability, recyclability, and short reaction time.
Upadhyay, Rahul,Singh, Deepak,Maurya, Sushil K.
supporting information
p. 3925 - 3931
(2021/08/24)

Design, Synthesis, and Cytotoxic Screening of New Quinoline Derivatives over MCF-7 Breast Cancer Cell Line
Abstract: VEGFR-2 inhibition represents an attractive strategy for anticancer drug design. A new series of quinoline derivatives were synthesized and structurally confirmed with different spectroscopic techniques. VEGFR-2 inhibition assay showed that 2-(4-bromoquinolin-3-yloxy)-1-(4-chlorophenyl)ethanone (V) demonstrated potent VEGFR-2 inhibitory activities. In addition, the brominated quinoline (V) exhibit antitumor activity over MCF-7 cell line via cell cycle arrest at G1 phase and apoptosis inducing activity as revealed by cell cycle analysis and Annexin V/FITC staining assays. Moreover, brominated quinoline (V) was proved to upregulate expression of proteins that trigger apoptosis such as increased Bax, decreased Bcl-2 as well as increased Bax/Bcl-2 ratio.
Amal, M. Imam,Islam, Zaki
p. 1099 - 1109
(2020/12/31)

Convenient synthesis of 3-Hydroxyquinolines via dakin oxidation: A short synthesis of Jineol
A convenient synthesis of 3-hydroxyquinolines has been described via unprecedented Dakin oxidation of quinoline-3-carboxaldehydes. Subsequently, application of the methodology to a high yielding synthesis of quinoline alkaloid Jineol (1) is reported.
Ghorai, Sujit K.,Dasgupta, Mayukh,Dutta, Piyali,Dumeunier, Raphael,Mal, Sanjib,Patre, Rupesh,Kuilya, Tapan Kumar,Pal, Sitaram,Manjunath, Bhanu N.
supporting information

(2020/08/06)

Highly Porous Polycaprolactone Membrane: A Biocompatible Promotor for Oxidative Hydroxylation of Arylboronic Acids
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Kwon, Gyu-Tae,Lim, In-Kyun,Shin, Ueon Sang,Kim, Seung-Hoi
supporting information
p. 574 - 577
(2020/05/25)

Palladium-Catalyzed Hydroxylation of Aryl Halides with Boric Acid
Boric acid, B(OH)3, is proved to be an efficient hydroxide reagent in converting (hetero)aryl halides to the corresponding phenols with a Pd catalyst under mild conditions. Various phenol products were obtained in good to excellent yields. This transformation tolerates a broad range of functional groups and molecules, including base-sensitive substituents and complicated pharmaceutical (hetero)aryl halide molecules.
Song, Zhi-Qiang,Wang, Dong-Hui
supporting information
p. 8470 - 8474
(2020/11/18)

Multi-Functional Oxidase Activity of CYP102A1 (P450BM3) in the Oxidation of Quinolines and Tetrahydroquinolines
Tetrahydroquinoline, quinoline, and dihydroquinolinone are common core motifs in drug molecules. Screening of a 48-variant library of the cytochrome P450 enzyme CYP102A1 (P450BM3), followed by targeted mutagenesis based on mutation-selectivity correlations from initial hits, has enabled the hydroxylation of substituted tetrahydroquinolines, quinolines, and 3,4-dihydro-2-quinolinones at most positions around the two rings in good to high yields at synthetically relevant scales (1.5 g L?1 day?1). Other oxidase activities, such as C?C bond desaturation, aromatization, and C?C bond formation, were also observed. The enzyme variants, with mutations at the key active site residues S72, A82, F87, I263, E267, A328, and A330, provide direct and sustainable routes to oxy-functionalized derivatives of these building block molecules for synthesis and drug discovery.
Li, Yushu,Wong, Luet L.
p. 9551 - 9555
(2019/08/06)

Room-Temperature Ionic Liquids (RTILs) as Green Media for Metal- and Base-Free ipso -Hydroxylation of Arylboronic Acids
The oxidative hydroxylation of arylboronic acids to the corresponding phenolic compounds under metal- and base-free aerobic conditions is successfully demonstrated on a greener media. Hydrogen peroxide, as an eco-friendly oxidant, is compatible with green mediates room-temperature ionic liquids (RTIL)s, providing hydroxylation products of arylboronic acids in an efficient manner. The RTIL support is particularly interesting for its reusability.
Kim, Seung-Hoi,Kwon, Gyu-Tae,Shin, Eun-Jae
supporting information
p. 1815 - 1819
(2019/09/09)

Recyclable CNT-chitosan nanohybrid film utilized in copper-catalyzed aerobic ipso-hydroxylation of arylboronic acids in aqueous media
A convenient heterogeneous catalytic system consisting of recyclable and reusable carbon nanotube-chitosan nanohybrid film and copper salt was developed for the aerobic ipso-hydroxylation of arylboronic acids. A variety of arylboronic acids bearing electron-withdrawing or electron-donating groups were smoothly transformed at room temperature in water to afford the corresponding phenols in high yields.
Kim, Han-Sem,Joo, Sung-Ryu,Shin, Ueon Sang,Kim, Seung-Hoi
p. 4597 - 4601
(2018/11/23)

Benzoxazole-Linked Ultrastable Covalent Organic Frameworks for Photocatalysis
The structural uniqueness of covalent organic frameworks (COFs) has brought these new materials great potential for advanced applications. One of the key aspects yet to be developed is how to improve the robustness of covalently linked reticular frameworks. In order to make the best use of π-conjugated structures, we develop herein a ";killing two birds with one stone" strategy and construct a series of ultrastable benzoxazole-based COFs (denoted as LZU-190, LZU-191, and LZU-192) as metal-free photocatalysts. Benefiting from the formation of benzoxazole rings through reversible/irreversible cascade reactions, the synthesized COFs exhibit permanent stability in the presence of strong acid (9 M HCl), strong base (9 M NaOH), and sunlight. Meanwhile, reticulation of the benzoxazole moiety into the π-conjugated COF frameworks decreases the optical band gap and therefore increases the capability for visible-light absorption. As a result, the excellent photoactivity and unprecedented recyclability of LZU-190 (for at least 20 catalytic runs, each with a product yield of 99%) have been illustrated in the visible-light-driven oxidative hydroxylation of arylboronic acids to phenols. This contribution represents the first report on the photocatalytic application of benzoxazole-based structures, which not only sheds new light on the exploration of robust organophotocatalysts from small molecules to extended frameworks but also offers in-depth understanding of the structure-activity relationship toward practical applications of COF materials.
Wei, Pi-Feng,Qi, Ming-Zhu,Wang, Zhi-Peng,Ding, San-Yuan,Yu, Wei,Liu, Qiang,Wang, Li-Ke,Wang, Huai-Zhen,An, Wan-Kai,Wang, Wei
supporting information
p. 4623 - 4631
(2018/04/10)

C70 Fullerene-Catalyzed Metal-Free Photocatalytic ipso-Hydroxylation of Aryl Boronic Acids: Synthesis of Phenols
A metal-free C70 fullerene-catalyzed method has been developed for the ipso-hydroxylation of aryl and heteroaryl boronic acids to corresponding phenols under photocatalytic conditions. The reaction proceeds under oxygen atmosphere and the mechanistic study revealed that C70 plays a critical role in the generation of reactive oxygen species in the presence of blue light. Reactions in the presence of 18O-labelled water and oxygen confirmed the generation of reactive oxygen species from oxygen molecule. Amine used as a reductant could be recovered in the form of imine. The current method is also applicable to the synthesis of aryl ethers in one-pot two-step process. (Figure presented.).
Kumar, Inder,Sharma, Ritika,Kumar, Rakesh,Kumar, Rakesh,Sharma, Upendra
supporting information
p. 2013 - 2019
(2018/04/02)

Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions
The combination of Cu(acac)2 and N,N′-bis(4-hydroxyl-2,6-dimethylphenyl)oxalamide (BHMPO) provides a powerful catalytic system for hydroxylation of (hetero)aryl halides. A wide range of (hetero)aryl chlorides bearing either electron-donating or -withdrawing groups proceeded well at 130 °C, delivering the corresponding phenols and hydroxylated heteroarenes in good to excellent yields. When more reactive (hetero)aryl bromides and iodides were employed, the hydroxylation reactions completed at relatively low temperatures (80 and 60 °C, respectively) at low catalytic loadings (0.5 mol % Cu).
Xia, Shanghua,Gan, Lu,Wang, Kailiang,Li, Zheng,Ma, Dawei
supporting information
p. 13493 - 13496
(2016/10/31)

Continuous-flow synthesis of functionalized phenols by aerobic oxidation of grignard reagents
Phenols are important compounds in chemical industry. An economical and green approach to phenol preparation by the direct oxidation of aryl Grignard reagents using compressed air in continuous gas-liquid segmented flow systems is described. The process tolerates a broad range of functional groups, including oxidation-sensitive functionalities such as alkenes, amines, and thioethers. By integrating a benzyne-mediated in-line generation of arylmagnesium intermediates with the aerobic oxidation, a facile three-step, one-flow process, capable of preparing 2-functionalized phenols in a modular fashion, is established. Putting on airs: Aerobic oxidation of (hetero)aryl Grignard reagents using compressed air proceeds with a gas-liquid continuous-flow system, thus enabling preparation of fucntionalized phenols. By integrating an in-line generation of ArMgBr intermediates with the aerobic oxidation, ortho-functionalized phenols can be assembled. The method demonstrates good functional-group (FG) compatibility, mild reaction conditions, and short reaction times.
He, Zhi,Jamison, Timothy F.
supporting information
p. 3353 - 3357
(2014/04/03)

First identification of boronic species as novel potential inhibitors of the Staphylococcus aureus NorA efflux pump
Overexpression of efflux pumps is an important mechanism of bacterial resistance that results in the extrusion of antimicrobial agents outside the bacterial cell. Inhibition of such pumps appears to be a promising strategy that could restore the potency of existing antibiotics. The NorA efflux pump of Staphylococcus aureus confers resistance to a wide range of unrelated substrates, such as hydrophilic fluoroquinolones, leading to a multidrug-resistance phenotype. In this work, approximately 150 heterocyclic boronic species were evaluated for their activity against susceptible and resistant strains of S. aureus. Twenty-four hit compounds, although inactive when tested alone, were found to potentiate ciprofloxacin activity by a 4-fold increase at concentrations ranging from 0.5 to 8 μg/mL against S. aureus 1199B, which overexpresses NorA. Boron-free analogues showed no biological activity, thus revealing that the boron atom is crucial for biological activity. This work describes the first reported efflux pump inhibitory activity of boronic acid derivatives.
Fontaine, Fanny,Hequet, Arnaud,Voisin-Chiret, Anne-Sophie,Bouillon, Alexandre,Lesnard, Aurélien,Cresteil, Thierry,Jolivalt, Claude,Rault, Sylvain
p. 2536 - 2548
(2014/04/17)

Copper MOF: Scope and limitation in catalytic hydroxylation and nitration of aryl halides
The potential catalytic application of MOFs like [Cu3(btc) 2] (btc=1,3,5-benzenetricarboxylate), [Cu(bdc)] (bdc=1,4- benzenedicarboxylate), [Cu(pymo)2] (pymo=2-hydroxypyrimidinalote) and [Cu(im)2] (im=imidazolate) was explored in the hydroxylation and nitration of aryl halides. Cu3(btc)2 was found to be superior for both the reactions furnishing good to excellent yields of the respective products. The studies demonstrated that MOFs are not recyclable, attributable to their instability in the highly polar and basic conditions demanded for these reactions. Complete transformation of MOFs to copper oxide nanoparticles occurred in hydroxylation, whereas significant alteration in frameworks was observed for the recovered catalyst in nitration.
Priyadarshini,Amal Joseph,Kantam, M. Lakshmi,Sreedhar
p. 6409 - 6414
(2013/07/26)

Me3(OMe)tBuXPhos: A surrogate ligand for Me4tBuXPhos in palladium-catalyzed C-N and C-O bond-forming reactions
A new biarylphosphine ligand, Me3(OMe)tBuXPhos (L3), was designed as a surrogate for Me4tBuXPhos (L1). The Me 3(OMe)tBuXPhos could be prepared in a chromatography-free manner from inexpensive and readily available 2,3,6-trimethylphenol. Comparative studies demonstrated that a catalyst based on Me3(OMe)tBuXPhos displayed the same reactivity as a catalyst based on Me4tBuXPhos for Pd-catalyzed C-N and C-O bond-forming processes.
Ueda, Satoshi,Ali, Siraj,Fors, Brett P.,Buchwald, Stephen L.
experimental part
p. 2543 - 2547
(2012/05/20)

Mild and rapid hydroxylation of aryl/heteroaryl boronic acids and boronate esters with N-oxides
Aryl and heteroaryl boronic acids and boronate esters are rapidly, often within minutes, transformed into the corresponding phenols by N-oxides in an open flask at ambient temperature. This transformation has broad compatibility with a variety of functional groups.
Zhu, Chen,Wang, Rui,Falck
supporting information; experimental part
p. 3494 - 3497
(2012/08/28)

NOVEL AROMATIC COMPOUND AND POLYARYLENE COPOLYMER HAVING NITROGEN-CONTAINING HETEROCYCLE INCLUDING SULFONIC ACID GROUP IN SIDE CHAIN
Provided is a solid polymer electrolyte having increased heat resistance and high proton conductivity and a proton conductive membrane composed of the electrolyte. Also provided is a copolymer having a sulfonic acid group. The copolymer includes a repeating unit represented by Formula (1): (in the formula, Y denotes at least one kind of structure selected from the group consisting of —CO—, —SO2—, —SO—, —CONH—, —COO—, —(CF2)l— (l is an integer of 1 to 10), and —C(CF3)2—; W denotes at least one kind of structure selected from the group consisting of a direct bond, —CO—, —SO2—, —SO—, —CONH—, —COO—, —(CF2)l— (l is an integer of 1 to 10), —C(CF3)2—, —O—, and —S—; Z denotes a direct bond or at least one kind of structure selected from the group consisting of —(CH2)l—(l is an integer of 1 to 10), —C(CH3)2—, —O—, —S—, —CO—, and —SO2—; R30 denotes a nitrogen-containing aromatic ring having a substituent represented by —SO3H, —O(CH2)hSO3H, or —O(CF2)hSO3H (h is an integer of 1 to 12); p is an integer of 0 to 10; q is an integer of 0 to 10; r is an integer of 1 to 5; and k is an integer of 0 to 4).
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(2010/06/22)

NOVEL ACETYL-COA CARBOXYLASE (ACC) INHIBITORS AND THEIR USE IN DIABETES, OBESITY AND METABOLIC SYNDROME
The present invention relates to compounds of formula (I) which inhibit acetyl-CoA carboxylase (ACC) and are useful for the prevention or treatment of metabolic syndrome, type II diabetes, obesity, atherosclerosis and cardiovascular diseases in humans.
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Page/Page column 24

(2008/06/13)

The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans
The direct and selective synthesis of phenols from aryl/heteroaryl halides and KOH has been achieved through the use of highly active monophosphine-based catalysts derived from Pd2dba3 and ligands L1 or L2 and the biphasic solvent system 1,4-dioxane/H2O. We have also demonstrated a one-pot method of phenol formation/alkylation for the preparation of alkyl aryl ethers from aryl halides. In many instances, this protocol overcomes limitations in existing Pd-catalyzed coupling reactions of aliphatic alcohols with aryl halides. Finally, we demonstrate that substituted benzofurans can be prepared efficiently via a Pd-catalyzed phenol formation/cyclization protocol starting from 2-chloroaryl alkynes. Copyright
Anderson, Kevin W.,Ikawa, Takashi,Tundel, Rachel E.,Buchwald, Stephen L.
p. 10694 - 10695
(2007/10/03)

SALTS AND POLYMORPHS OF A POTENT ANTIDIABETIC COMPOUND
Salts and polymorphs of a compound useful in the treatment of inflammatory and metabolic conditions and diseases are provided herein. In particular, the invention provides salts and polymorphs of a compound which modulates the expression and/or function of a peroxisome proliferator-activated receptor. The salts and polymorphs are useful for the treatment or prevention of conditions and disorders associated with energy homeostasis such as type II diabetes, lipid metabolism, adipocyte differentiation and inflammation.
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Page/Page column 36

(2008/06/13)

Efficient nucleophilic substitution reactions of quinolyl and isoquinolyl halides with nucleophiles under focused microwave irradiation
Nucleophilic substitution reactions of 2-chloroquinoline, 3-bromoquinoline and 4-bromoisoquinoline with thiolate, alkoxy ions and aniline were completed within several minutes under microwave irradiation. This method gives the desired products with yields up to 99% in a short reaction time, and is superior to the classical heating process.
Cherng, Yie-Jia
p. 1125 - 1129
(2007/10/03)

An efficient facile and selective hydroxylation of nitrogen heterocycles
Nitrogen heterocycles have been efficiently hydroxylated under mild and neutral conditions by employing Cupric nitrate/phosphate buffer/30%hydrogen peroxide system. The present method afforded the biologically active and important hydroxy heterocycles. Th
Nasreen, Aayesha,Adapa, Srinivas R.
p. 501 - 506
(2007/10/03)

Desazadesmethyldesferrithiocin analogues as orally effective iron chelators
Further structure-activity studies of desferrithiocin analogues are carried out. (S)-Desazadesmethyldesferrithiocin, 2-(2-hydroxyphenyl)-Δ2- thiazoline-4(S)-carboxylic acid, serves as the principal framework in the current paper. Desazadesmethyldesferrithiocin can be structurally altered with facility, and data are already available on its iron-clearing properties and toxicity parameters. Four different kinds of structural modifications of this framework are undertaken: introduction of hydroxy, carboxy, or methoxy groups on the aromatic ring; alteration of the thiazoline ring; increasing the distance between the ligand donor atoms; and benz-fusion of the aromatic rings. The structural modifications described are shown to have a tremendous impact on both the iron clearance and toxicity profiles of the desazadesmethyldesferrithiocin molecule. All of the compounds are assessed in a bile-duct-cannulated rodent model to determine iron clearance efficiency. Ligands which demonstrate an efficiency of greater than 2% are carried forward to the iron-overloaded primate for iron-clearing measurements. Ligands with efficiencies greater than 3% in the primate are then evaluated in a formal toxicity study in rodents. On the basis of the results of the present work, 2-(2,4-dihydroxyphenyl)-Δ2-thiazoline-4(S)-carboxylic acid is a promising candidate for clinical evaluation.
Bergeron, Raymond J.,Wiegand, Jan,Weimar, William R.,Vinson, J. R. Timothy,Bussenius, J?rg,Yao, Guo Wei,McManis, James S.
p. 95 - 108
(2007/10/03)

Bipyridyls and their use as inks
Process employing bipyridyls as inks, of the general formula STR1 in which R, R' are, for example, alkyl and R1, R2, R3, R4, R5, R6 are, for example hydrogen or alkyl radicals, or R1 and R2 or R2 and R3, and/or R4 and R5 or R5 and R6 together with the pyridine ring form in isoquinoline or quinoline ring system.
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(2008/06/13)

Structure and Stereochemistry of cis-Dihydro Diol and Phenol Metabolites of Bicyclic Azaarenes from Pseudomonas putida UV4
Biotransformation of quinoline, isoquinoline, quinoxaline and quinazoline using growing cultures of Pseudomonas putida UV4 yielded cis-dihydro diols from the oxidation of the carbocyclic aromatic ring.Aromatic hydroxylation was observed in both carbocyclic and heterocyclic rings.Ring cleavage of the quinoline skeleton to yield anthranilic acid, and cis-diol formation (with alkene bond reduction) to yield cis-5,6,7,8-tetrahydroquinazoline-5,6-diol from quinazoline were observed.The cis-dihydro diol metabolites of quinoline (5,6- and 7,8-) and quinoxaline (5,6-) were found to be optically pure, while metabolism of isoquinoline gave on e homochiral (5,6-) and one racemic 7,8-) cis-dihydro diol product.The absolute configuration of the cis-dihydro diol metabolites have been determined using 1H NMR analyses, stereochemical correlations and X-ray crystallography methods.
Boyd, Derek R.,Sharma, Narain D.,Dorrity, Michael R. J.,Hand, Mark V.,McMordie, R. Austin S.,et al.
p. 1065 - 1072
(2007/10/02)

Quinolinoxy phenylsulphonamides
New phenylsulphonamide of the formula in which STR1 R1 represents a pyridyl, quinolyl or isoquinolyl radical which is unsubstituted or substituted by halogen, alkyl, cycloalkyl, alkoxy, cyano, nitro, halogenoalkyl, halogenoalkoxy, alkoxycarbonyl or alkylsulphonyl, R2 represents hydrogen, cyano, nitro, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or alkoxycarbonyl, R3 represents an aryl radical which is unsubstituted or monosubstituted, disubstituted or trisubstituted by halogen, halogenoalkyl, halogenoalkoxy, alkyl, alkoxy, alkylthio, alkylsulphonyl, cyano, nitro or alkoxycarbonyl, the substituents being identical or different, or represents pentafluorophenyl or represents a straight-chain, branched or cyclic alkyl which is unsubstituted or substituted by halogen, aryl, aryloxy, cyano, alkoxycarbonyl, alkoxy, alkylthio or trifluoromethyl, and X represents an --O--, --A--B-- or --B--A-- group where A denotes --O--, STR2 and B denotes --CH2 -- or STR3 where R1 does not represent a pyridyl radical when x represents an --O-- group, and salts thereof are prepared by reacting appropriate amines with sulphonyl halides. The substituted phenylsulphonamides can be employed as active compounds for inhibiting enzymatic reactions and for inhibiting thrombocyte aggregations.
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(2008/06/13)

A Simple Synthesis of Dihydroxybipyridyls
Dihydroxybipyridyls (dihydroxybipyridines), laser dyes with large Stokes shifts, are prepared by a simple one-step synthesis from the corresponding 2-bromo-3-hydroxypyridines, 3-bromo-4-hydroxyisoquinoline and 2-bromo-3-hydroxyquinoline, using zinc, and nickel(0) in yields up to 45percent.
Naumann, Christoph,Langhals, Heinz
p. 279 - 281
(2007/10/02)

Metabolism of Bicyclic Aza-arenes by Pseudomonas putida to Yield Vicinal cis-Dihydrodiols and Phenols
Metabolism of the aza-arenes quinoline, isoquinoline, quinazoline, and quinoxaline by a mutant strain of the bacterium Pseudomonas putida resulted in attack at the carbocyclic ring (to yield stable cis-dihydrodiols and phenols) and at the heterocyclic ring (to yield phenols and ring cleavage products).
Boyd, Derek R.,McMordie, R. Austin S.,Porter, H. Patricia,Dalton, Howard,Jenkins, Richard O.,Howarth, Oliver W.
p. 1722 - 1724
(2007/10/02)

Metabolites of quinoline, a hepatocarcinogen in a subcellular microsomal system
It was evidenced that quinoline was metabolized to quinoline 1-oxide catalyzed by cytochrome P-450-linked mixed function monooxygenase system and to 5,6-trans-dihydroxy-5,6-dihydroquinoline by cytochrome P-448-linked one. The third metabolite, 3-hydroxyquinoline, may be produced in another course of metabolism, which might be connected with genotoxicity of quinoline, as previously discussed.
Tada,Takahashi,Kawazoe
p. 3834 - 3837
(2007/10/02)

TOTAL REACTIVITY OF PYRIDINE AND QUINOLINE VIA THE REACTIONS OF ARYLBENZOATES WITH HYDROXIDE ION. APPARENT SUBSTITUENT CONSTANS FOR SOME N-HETEROAROMATIC GROUPS
A new set of apparent ? values was evaluated for the aza substitution of all positions in pyridyl and quinolyl groups on the basis of the alkaline hydrolysis of aryl benzoates.The enhanced reactivities of 4-pyridyloxy- and 4-quinolyloxy- groups were first estimated quantitatively.
Sawada, Masami,Ichihara, Masaharu,Ando, Takashi,Yukawa, Yasuhide,Tsuno, Yuho
p. 4733 - 4736
(2007/10/02)