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研究成果report

公表論文

Toshihiro Nohara,*, Yukio Fujiwara, Yusuke Komota, Yoshihiko Kondo, Taiki Saku, Koki Yamaguchi, Yoshihiro Komohara, and Motohiro Takeya
Cyclic Sulfoxides-Garlicnins K1, K2, and H1-Extracted from Allium sativum
Chem. Pharm. Bull., 2015, 63, 117-121.

Masashi Eto,* Koki Yamaguchi, Akiko Watanabe, Kazunobu Harano
Isolable Atropisomers of 2-Aryl Indoline Derivatives: Determination of Rotational Barrier by Density Functional Theory Approach
Tetrahedron, 2014, 70 (9), 1811-1817.

Toshihiro Nohara*, Yukio Fujiwara, Rino Kudo, Koki Yamaguchi, Tsuyoshi Ikeda,
Kotaro Murakami, Masateru Ono, Tetsuya Kajimoto, and Motohiro Takeya
Isolation and Characterization of New Onionins A2 and A3 from Allium cepa, and of Onionins A1, A2, and A3 from Allium fistulosum
Chem. Pharm. Bull., 2014, 62 (11), 1141-1145.

Toshihiro Nohara, Yukio Fujiwara, Tsuyoshi IKeda, Koki Yamaguchi, Hideyuki Manabe, Kataro MUrakami, Masateru Ono, Daisuke Nakano, Junei Kinjo
Acyclic Sulfides, Garlicnins L-1-L-4, E, and F, from Allium sativum
Chem. Pharm. Bull., 2014, 62 (5), 477-482.

Hideaki Shimada, Takahiko Tanigawa, Kazunori Matayoshi, Kazufumi Katakura, Ken Babazono, Hiroyuki Takayama, Tsuyoshi Murahashi, Hiroyuki Akita, Toshiyuki Higuchi, Masashi Eto, Yorishige Imamura
Comparative inhibition of tetrameric carobonyl reductase activity in pig heart cytosol by alkyl 4-pyridyl ketones
J. Enzyme. Inhib. Med. Chem., 2014, 29 (3), 397-400.

Koki Yamaguchi, Masashi Eto*, Kazunobu Harano
Formation Mechanism of Triketo Cage Compounds from Reaction of Phencyclone with Benzoquinones: Cascade Reaction of Intermolecular [4+2]π and Intramolecular [2+2]π Cycloadditions
Chem. Pharm. Bull., 2013, 61 (10), 1065-1070.

Koki Yamaguchi, Kazunobu Harano, Masashi Eto*
ROLE OF CH/O AND CH/p INTERACTIONS IN STRUCTURAL STABILITY. EFFECT ON ENDO SELECTIVITY IN 1,3-DIPOLAR REACTION OF ELECTRON-DEFICIENT 4-OXO-4H-PYRAZOLE 1,2-DIOXIDES WITH N-SUBSTITUTED MALEIMIDES
Heterocycles
, 2013, 87(2) , 319-328.

Koki Yamaguchi, Masashi Eto*, Yasuyuki Yoshitake, Kazunobu Harano
Thermal Reaction of Electron Deficient 4-Oxo-4H-pyrazole 1,2-Dioxide with Cycloheptatriene: The First Examples of the Formation of an Endo-[4π+6π]-cycloadduct and an Intramolecular 1,3-Dipolar Reaction Leading to a Heterocage
J. Phys. Org. Chem., 2013, 26, 64-69.

Masateru Ono,* Chisato Furusawa, Kana Matsumura, Sayuri Noguchi, Shin Yasuda, Masafumi Okawa, Junei Kinjo, Masashi Eto, Koki Yamaguchi, Hitoshi Yoshimitsu, Toshihiro Nohara
A new diterpenoid from the leaves of Clerodendron trichotomum
J. Nat. Med., 2013, 67, 404-409.

Masaki Abe, Masashi Eto,*, Koki Yamaguchi, Masatoshi Yamasaki, Junichi Misaka, Yasuyuki Yoshitake, Masami Otsuka, Kazunobu Harano
Clathrate formation of DielseAlder adduct of phencyclone and acenaphthylene. Key role of CH/π and bidentate CH/O interactions of the phenanthrene ring in construction of host framework
Tetrahedron, 2012, 68, 3566-3576.

Daisuke Iohara, Kenshi Yoshida, Kohki Yamaguchi, Makoto Anraku, Keiichi Motoyama, Hidetoshi Arima, Kaneto Uekama, and Fumitoshi Hirayama*
Cyclodextrin-Induced Change in Crystal Habit of Acetylsalicylic Acid in Aqueous Solution
Cryst. Growth Des., 2012, 12, 1985-1991.

Koki Yamaguchi, Masashi Eto,* Kenta Higashi, Yasuyuki Yoshitake, and Kazunobu Harano
DABCO-Triggered mild cascade reaction of electron-deficient cyclopentadienone: facile and efficient synthesis of condensed carbocycles
Tetrahedron Lett., 2011, 52(46), 6082-6085

Masashi Eto,* Koki Yamaguchi, Itaru Shinohara, Fumikazu Ito, Yasuyuki Yoshitake, and Kazunobu Harano
Role of edge-to-face interaction between aromatic rings in clathrate formation of 1-benzoyl-2-hydroxyindoline derivatives with benzene. X-ray crystal and PM6 analyses of the interaction
Tetrahedron, 2011, 67 (38), 7400-7405.

Masashi ETO, Koki YAMAGUCHI, Yasuyuki YOSHITAKE, Kazunobu HARANO*
Formation Mechanism of Furfuryl Sulfides from O-Furfuryl Dithiocarbonates: Density Functional Theory Study for Aromatic [3,3]-Sigmatropic Rearrangement
Chem. Pharm. Bull., 2011, 59 (6), 681-685.

Masashi ETO, Koki YAMAGUCHI, Yasuyuki YOSHITAKE, Kazunobu HARANO*
New Formation Mechanism of Allylic Trithiocarbonates from Sodium O-(2-Alkenyl) Dithiocarbonates via Sequential Pericyclic Reactions: Density Functional Theory Study
Chem. Pharm. Bull., 2010, 58, 1517-1520.

H. Shimada,* M. Eto, M. Ohtaguro, M. Ohtsubo, Y. Mizukami, T. Ide and Y. Imamura
Differential Mechanisms for the Inhibition of Human Cytochrome P450 1A2 by Apigenin and Genistein
J. Biochem. Mol. Toxicol., 2010, 24, 230-234.

Masashi Eto, Koki Yamaguchi, Itaru Shinohara, Fumikazu Ito, Yasuyuki Yoshitake, Kazunobu Harano*
Conformation of aromatic rings in isolable atropisomers of 2-arylindoline derivatives and kinetic evidences for π-π interaction
Tetrahedron, 2010, 66, 898-903.

Kazuhide Nakahara, Shinji Takechi, Koki Yamaguchi, Kazunobu Harano and Tadatoshi Yamaguchi*
Tetraazaindenes derived from dihydropyrazines with DNA strand-breaking activity
Chem. Pharm. Bull., 2009, 57(12), 1371-1375.

Yasuyuki Yoshitake, Koki Yamaguchi, and Kazunobu Harano*
FORMATION PATHWAY OF NOVEL CYCLOADDUCT OBTAINED BY REACTION OF 3,5-DISUBSTITUTED 4-OXO-4H-PYRAZOLE 1,2-DIOXIDE WITH DIMETHYL ACETYLENEDICARBOXYLATE

Heterocycles, 2009, 78(11) , 2777-2785.

Kazuhide Nakahara, Koki Yamaguchi, Yasuyuki Yoshitake, Tadatoshi Yamaguchi and Kazunobu Harano* Chemical Reactivity of Dihydrohyrazine Derivatives. Cylcoaddition Behavior toward Ketenes
Chem. Pharm. Bull., 2009, 57 (4), 846-852.

Koki Yamaguchi, Masashi Eto, Yasuyuki Yoshitake, Kazunobu Harano*
Crystallographic Evidence for Cyclopropane Ring Formation in Isotwistenes Obtained by Thermal Cascade Reactions of Cyclopentadienone with Acyclic Conjugated Dienes
Chem. Pharm. Bull., 2009, 57(7), 749―751.

Masashi Eto, Fumikazu Ito, Hidetoshi Sato, Itaru Shinohara, Koki Yamaguchi, Yasuyuki Yoshitake, Kazunobu Harano*
Role of 2-Naphthyl Ether Intermediate in Formation of Isolable Atropisomers Derived from the Coupling Reaction of (2-Hydroxy-3,3-dimethylindolin-1-yl) (Substituted phenyl) methanones with 2-Naphthol
Heterocycles, 2009, 78(6), 1485-1496.

Masashi Eto,* Chikako Masuoka, Toru Yamasaki, Kazunobu Harano and Masateru Ono
Molecular Orbital Analysis of Antioxidative Activity of Phenolics from Tessaria integrifolia and Piper elongatum
Food Science and Technology Research, 2008, 14(4), 415-420.

Naoko Kiyota, Kazushi Shingu, Koki Yamaguchi, Yasuyuki Yoshitake, Kazunobu Harano, Hitoshi Yoshimitsu, Hiroyuki Miyashita, Tsuyoshi Ikeda, Chie Tagawa and Toshihiro Nohara*
New C(28) steroidal glycosides from Tubocapsicum anomalum
Chem. Pharm. Bull., 2008, 56(7), 1038-1040.

Yoichiro Nishida, Masashi Eto, Hiroyuki Miyashita, Tsuyoshi Ikeda, Koki Yamaguchi, Hitoshi Yoshimitsu, Toshihiro Nohara and Masateru Ono*
A new homostilbene and two new homoisoflavones from the bulbs of Scilla scilloides
Chem. Pharm. Bull., 2008, 56(7), 1022-1025.

Akiko Watanabe, Koki Yamaguchi, Fumikazu Ito, Yasuyuki Yoshitake and Kazunobu Harano*
Reaction of 1-acyl and aroyl-2-hydroxy-3,3-dimethylindoline with arylamines catalyzed by BF3-etherate. formation of 12,12a-dihydroindolo[1,2-c]quinazoline
Heterocycle, 2007, 71 (2), 343-359.

Naoko KIYOTA, Kazushi SHINGU, Koki YAMAGUCHI, Yasuyuki YOSHITAKE, Kazunobu HARANO, Hitoshi YOSHIMITSU, Tsuyoshi IKEDA, and Toshihiro NOHARA*
New C_28 Steroidal Glycosides from Tubocapsicum anomalum
Chem. Pharm. Bull., 2007, 55 (1), 34-36.

Koki Yamaguchi, Kenji Utsumi, Yasuyuki Yoshitake, and Kazunobu Harano*
Cyclization reaction of cyclopentadienone with prop-2-yn-1-ol in priority to Diels-Alder reaction
Tetrahedron Lett., 2006, 47, 4235-4239.

Koki Yamaguchi, Saori Nakatomi, Yasuyuki Yoshitake, and Kazunobu Harano*
A Novel clathrate host allowing structural adjustment during the inclusion of 1,2-diaminoethanes
Tetrahedron Lett., 2005, 46(7), 1087-1090.

Koki Yamaguchi, Chika Kai, Yasuyuki Yoshitake, and Kazunobu Harano*
Another Aspect of the Reaction Behavior of Cyclopentadienones. 1,5-Sigmatropic Rearrangement of the 1,4-Addition Products of Amines
Eur. J. Org. Chem., 2004, 4, 826-834.

Shigeru OISO, Yasuyuki YOSHITAKE, Masashi ETO and Kazunobu HARANO*
Pericyclic Reaction of Ketenes with Cascade Reaction Products of Pyridine N-Oxides and Dipolarophiles. X-Ray Structures of the Adducts and Formation Mechanism
Chem. Pharm. Bull., 2003, 51(9), 1068-1074.

Fumikazu Ito, Tetsuya Moriguchi, Yasuyuki Yoshitake, Masashi Eto, Shoji Yahara and Kazunobu Harano*
Atropisomers of 1-(Acyl or Aroyl)-2-naphthylindolines. Isolation, X-Ray Crystal Structure and Conformational Analysis
Chem. Pharm. Bull., 2003, 51(6), 688-696.

Yasuyuki Yoshitake, Junichi Misaka, Masatoshi Yamasaki, Masashi Eto and Kazunobu Harano*
Carboxylic-acid clathrate hosts of Diels-Alder adducts of phencyclone and 2-alkenoic acids. Role of bidentate C-H--O hydrogen bonds between the phenanthrene and carbonyl groups in host-host network
Organic & Biomolecular Chemistry, 2003, 1(7), 1240-1249.

Shigeru OISO, Yasuyuki YOSHITAKE, Masashi ETO and Kazunobu HARANO
Cascade Reaction of Imines with Phenylsulfinylallene. X-Ray Structure of the Product and its Formation Mechanism
Chem. Pharm. Bull., 2002, 50(11), 1525-1527.

Yasuyuki Yoshitake, Junichi Misaka, Koji Setoguchi, Masaki Abe, Tomohiro Kawaji, Masashi Eto and Kazunobu Harano*
Non-hydroxylic Clathrate Hosts of [4+2]pi Cycloadducts of Phencyclone and N-Arylmaleimides. Recognition of Aromatic Guests
J. Chem. Soc. Perkin Trans. 2, 2002, 9, 1161-1169.

Yasuyuki Yoshitake, Koki Yamaguchi, Chika Kai, Takayo Akiyama, Chiaki Handa, Tamaki Jikyo and Kazunobu Harano*
Cyclization of Electron-Deficient Cyclopentadienone with 2-Alkenyl and 2-Alkynylamines via Sequential Pericyclic Reaction Pathway
J. Org. Chem., 2001, 66(26), 8902-8911.

Yasuyuki Yoshitake, Hidetoshi Nakagawa and Kazunobu Harano*
Theoretical Study of Neighboring-group Participation in Thione-to-Thiol Rearrangement of Xanthates. Molecular Orbital Calculations using Conductor like Screening (COSMO) Models
Chem. Pharm. Bull., 2001, 49, 1433-1439.

Masashi Eto, Shoji Kubota, Hidetoshi Nakagawa, Yasuyuki Yoshitake and Kazunobu Harano*
Molecular Orbital Studies on Pericyclic Reactions of Cinnamyl Xanthates in β-Cyclodextrin Cavities
Chem. Pharm. Bull., 2000, 48(11), 1652-1659.

Yasuyuki Yoshitake, Hidetoshi Nakagawa, Masashi Eto and Kazunobu Harano*
A X-ray Crystallographic and Computational Study of Intermolecular Edge-to-Face Aromatic Interaction in Crystal Structure of Exo [4+2]π Cycloadduct of Phencyclone and S-Allyl S-Methyl Dithiocarbonate
Tetrahedron, 2000, 56, 6015-6021.

Yasuyuki Yoshitake, Hidetoshi Nakagawa, Masashi Eto and Kazunobu Harano *
Effect of >C=O--H-Ar Interaction on Endo/Exo Selectivity in the Diels-Alder Reaction of Phenyl-substituted Cyclopentadienones
Tetrahedron Lett., 2000, 41, 4395-4400.

A. Watanabe, T. Moriguchi, F. Ito, Y. Yoshitake, M. Eto and K. Harano*
X-RAY STRUCTURES OF A PAIR OF ATROPISOMERS OF 1-(3'-SUBSTITUTED BENZOYL)-2-NAPHTHYLINDOLINES AND SOME COMMENTS
Heterocycles, 2000, 53(1), 1-6.


*** その他の論文(2000年以前)****************************************************

T. Jikyo, M. Eto and K. Harano
Pericyclic Reactions of Cyclopentadienones with Nonactivated Olefins in Phenolic Solvents. Enhancement of the Reactivity and Periselectivity
Tetrahedron, 1999, 55, 6051-6066.

Y. Yoshitake, M. Eto and K. Harano
Crystallographic and Molecular Orbital Studies of Pyrazolone N,N-Dioxides. The Exceptionally Elongated N-N Bond
Chem. Pharm. Bull.,, 1999, 47(5), 601-606.

T. Yamaguchi, M. Eto, K. Harano, N. Kashige, K. Watanabe and S. Ito
New Compounds Derived from Dihydropyrazines Having DNA Strand Breakage Activity
Tetrahedron, 1999, 55, 675-686.

H. Nakagawa, M. Eto and K. Harano
CATALYTIC THIONE-TO-THIOL REARRANGEMENT OF XANTHATES BY 4-DIALKYLAMINOPYRIDINE. MO ANALYSIS OF THE CATALYTIC BEHAVIOR
Heterocycles, 1999, 51, 51-59.

Masashi Eto, Koji Setoguchi, Akiko Harada, Eri Sugiyama and Kazunobu Harano
Phencyclone Diels-Alder Adducts as a New Crystalline Host. Role of C-H/pi and C-H/O Interactions
Tetrahedron Lett., 1998, 39(52), 9751-9754.

T. Jikyo, M. Eto and K. Harano
Cycloaddition Behavior of Unsymmetric Cyclopentadienone. Peri- and Regioselectivities
J. Chem. Soc. Perkin Trans. 1, 1998, 3463-3470.

H. Nakagawa, M. Eto and K. Harano
Pyridine N-Oxide Catalyzed Thione-to-Thiol Rearrangement of Xanthates. MO Analysis of thr Reaction Mechanism
Tetrahedron, 1998, 54, 9333-9340.

M. Eto, O. Tajiri, H. Nakagawa and K. Harano
Correlation of Thione-to-thiol Rearrangement Rates of Xanthates with Solvent Scales. Analysis of the Reaction Behavior by the Kamlet-Taft Parameters, πi*, α and β
Tetrahedron, 1998, 54, 8009-8014.

Y. Yoshitake, M. Eto and K. Harano
Enhanced Endo Selectivity in 1,3-Dipolar Cycloaddition of Pyrazolone N,N Dioxides with Dipolarophiles having Ether and Carbonyl Groups. Role of the Remarkably Long N-N bond
Tetrahedron Lett., 1998, 39, 2761-2764.

Y. Yoshitake, M. Eto and K. Harano
1,3-Dipolar Cycloaddition Behavior of Pyrazolone N,N-Dioxides toward Epoxynaphthalene. Effective Secondary N---O Interaction between Addends
Heterocycles, 1997, 45, 1873-1878.

T. Jikyo, M. Eto and K. Harano
Pericyclic Reaction Behavior of Cyclopentadienones toward Acyclic Conjugated Dienes. [3,3]-Sigmatropic Rearrangement and Double Diels-Alder Reactions of the Endo[4+2] Cycloadducts
Chem. Pharm. Bull., 1997, 45, 1961-1969.

T. Jikyo, M. Eto and K. Harano
Ab initio Study of Formation and Structure of Double Diels-Alder Cycloadduct Derived from Sequential Pericyclic Reactions of 2-Pyrone with COD
Tetrahedron, 1997, 53, 12415-12424.

T. Jikyo, M. Eto, T. Matsuoka and K. Harano
p-Chlorophenol as a Solvent for Cycloaddition of Cyclopentadienones with Nonactivated Olefins
Org. Prep. Procd. Int., 1997, 29, 459-464.t

T. Yamaguchi, M. Eto, K. Watanabe, N. Kashige and K. Harano
Formation of Tricyclic Heterocycles from Condensation Reaction of 1,2-Diamines with 1,2-Diketones
Chem. Pharm. Bull., 1996, 44(10), 1977-1979.

M. Eto, T. Uemura, N. Shimizu and K. Harano
Sequential Pericyclic Reaction of Unsaturated Xanthates. Intramolecular Cycloaddition Selectivity of the 2,4-Alkadienyl 2-Alkenyl Sulfides
Tetrahedron, 1996, 52, 13909-13918.

M. Eto, F. Ito, T. Kitamura and K. Harano
X-Ray Structures of a Pair of Atropisomers of 1-Acyl-2-Arylindolines. Remarkable Through-Space Aryl-Aryl Interaction
Heterocycles, 1996, 43, 1159-1163.

M. Eto, M. Nishimoto, S. Kubota, T. Matsuoka and K. Harano
Retro-Ene Type Fragmentation of Allylic Dithiolcarbonates
Tetrahedron Lett., 1996, 37, 2445-2448.

T. Okawara, S. Ehara, H. Kogotani, Y. Okamoto, M. Eto, K. Harano, T. Yamasaki and M. Furukawa
Preparation and Stereochemistry of Dioxatetraazaperhydroanthracenes and -perylenes from the Reaction of 2-Hydrazinoethanols with Aldehydes and Glutaraldehyde
J. Org. Chem., 1996, 61(12), 4125-4129.

T. Matsuoka, S. Oiso, M. Eto and K. Harano*
Cycloaddition of Imines with Allene. Formation Mechanism of Azetidine Ring
Tetrahedron Lett., 1995, 36, 8031-8034.

M. Eto, M. Nishimoto, T. Uemura, T. Hisano and K. Harano*
Simple Synthesis of Furfuryl Sulfides via Extrusion of COS from the Xanthates and Its Mechanistic Aspects
J. Chem. Soc. Perkin Trans. 2, 1995, 1155-1162.

T. Okawara, S. Matsumoto, M. Eto, K. Harano and M. Furukawa
A Simple Preparation of 3-Carbamoylfuro[2,3-b]quinoxalin-2-ones
Heterocycles, 1995, 41(9), 1951-1958.

K. Harano, M. Eto, S. Kubota and T. Hisano
An Improved Preparation of 2,4-Dinitrophenyl Thioethers from Thiolcarbonates
Org. Prep. Proced. Int. , 1993, 25(1), 130-133.

K. Harano, M. Eto, K. Ono, K. Misaka and T. Hisano
Sequential Pericyclic Reactions of Unsaturated Xanthates. One-Pot Synthesis of Hydroisobenzothiophenes
J. Chem. Soc. Perkin Trans. 1, 1993, 299-307.

M. Eto, K. Harano and T. Hisano
Molecular Structure of the Double Diels-Alder Cycloadduct of 2-Pyrone and Cycloocta-1,5-diene. Very Close Intramolecuar H/H Contact and Some Comment
J. Chem. Soc. Perkin Trans. 2, 1993, 963-966.

K. Harano, M. Eto, T. Oya, S. Nakamoto and T. Hisano
Unexpected Cycloadducts from Reactions of Cyclopentadienone with Allylic Alcohols and Amines
Tetrahedron Lett., 1992, 33, 6473-6476.

K. Harano, K. Ono, M. Nishimoto, M. Eto and T. Hisano
A Simple One-Pot Synthesis of Hydroisobenzothiophenes via Three-Step Sequential Pericyclic Reactions of Xanthates
Tetrahedron Lett., 1991, 32, 2387-2390

K. Harano, T. Aoki, M. Eto and T.Hisano
Pericyclic Reaction of 2-Pyrones with Nonconjugated Dienes. Conformational Analysis of Double Diels-Alder Adducts by Molecular Mechanics Calculation
Chem. Pharm Bull., 1990, 38, 1182-1191.