2000年
-
・M. Kashiwayanagi, K. Tatani, S. Shuto, A. Matsuda,
Inward current responses to IP3 and adenophostin-analogues in turtle olfactory sensory neurons. Eur. J.
Neurosci., 2000, 12, 606-612.
-
・Y. Sumita, M. Shirato, Y. Ueno, A. Matsuda, S. Shuto, Toward the total
synthesis of cyclic ADP-carbocyclic-ribose. Formation of the
intramolecular pyrophosphate linkage by conformationally restriction in
a syn-form using a halogen substitution at the 8-position of the
adenine ring. Nucleosides Nucleotides, 2000, 19, 175-188.
-
・S. Shuto, I. Sugimoto, H. Abe, A. Matsuda, Mechanistic study of the
ring-enlargement reaction of (3-oxa-2-silacyclopentyl)methyl radicals
into 4-oxa-3-silacyclohexyl radicals. Evidence for a pentavalent
silicon-bridging radical transition state in 1,2-rearrangement
reactions of b-silyl radicals. J.
Am. Chem. Soc., 2000, 122, 1343-1351.
-
・M. Kanazaki, Y. Ueno, S. Shuto, A. Matsuda, Highly nuclease-resistant
phosphodiester-type oligodeoxynucleotides containing
4'a-C-aminoalkylthymidines form thermally stable duplexes with DNA and
RNA. A candidate for potent antisense molecules. J. Am. Chem. Soc., 2000, 122, 2422-2432.
- ・R. D.
Marwood, S. Shuto, D. J. Jenkins, B. V. L. Potter, Convergent
synthesis of adenophostin A analogues via a base replacement strategy. Chem. Commun., 2000, 219-220.
- ・H. Abe,
S. Shuto, A. Matsuda, Synthesis of the C-glycosidic analog of
adenophostin A, a potent IP3 receptor agonist, using a temporary
silicon-tethered radical coupling reaction as the key step. Tetrahedron
Lett., 2000, 41, 2391-2394.
- ・T.
Kodama, S. Shuto, M. Nomura, A. Matsuda, Synthesis of a
1’a-phenylselenouridine derivative as a synthetic precursor for various
1’-modified nucleosides, via enolization at the 1’-position of
3’,5’-O-TIPDS-2’-ketouridine. Tetrahedron
Lett., 2000, 41, 3643-3646.
- ・S. Shuto,
M. Terauchi, Y. Yahiro, H. Abe, S. Ichikawa, A. Matsuda,
Stereoselective synthesis of a- and b-C-glucosides via radical
cyclization with an allylsilyl tether. Control of the stereoselectivity
by changing the conformation of the pyranose ring. Tetrahedron Lett., 2000, 41, 4151-4155.
- ・Y.
Kazuta, S. Shuto, A. Matsuda, Highly stereoselective addition of
Grignard reagent to C-cyclopropylnitrone via the bisected s-trans
conformation. An efficient synthesis of PEDC, a potent NMDA receptor
antagonist having cyclopropane structure. Tetrahedron Lett., 2000, 41,5373-5377.
- ・H. Abe,
S. Shuto, A. Matsuda, Synthesis of the C-glycosidic analog of
adenophostin A and its uracil congener as potential IP3 receptor
ligands. Stereoselective construction of the C-glycosidic structure by
a temporary silicon-tethered radical coupling reaction. J. Org. Chem., 2000, 65, 4315-4325.
- ・M.
Nomura, S. Shuto, A. Matsuda, Development of an efficient
intermediate, a-[2-
(trimethylsilyl)ethoxy]-2-N-[2-(trimethylsilyl)ethoxycarbonyl]folic
acid, for the synthesis of folate (g)-conjugates, and its application
to the synthesis of folate-nucleoside conjugates. J. Org. Chem., 2000, 65, 5016-5021.
- ・M.
Fukuoka, S. Shuto, N. Minakawa, Y. Ueno, A. Matsuda, An efficient
synthesis of cyclic IDP- and cyclic 8-bromo-IDP-carbocyclic-riboses
using a modified Hata condensation method to form an intramolecular
pyrophosphate linkage as a key step. An entry to a general method for
the chemical synthesis of cyclic ADP-ribose analogs. J. Org. Chem., 2000, 65, 5238-5248.
- ・S. Shuto,
Y. Yahiro, S. Ichikawa, A. Matsuda, Synthesis of
3,7-anhydro-D-glycero-D-ido-octitol 1,5,6-trisphosphate as an IP3
receptor ligand using a radical cyclization reaction with a vinylsilyl
tether as the key step. Conformational restriction strategy using
steric repulsion between adjacent bulky protecting groups on a pyranose
ring. J. Org. Chem., 2000, 65, 5547-5557.
- ・S. Shuto,
K. Haramuishi, M. Fukuoka, A. Matsuda, Synthesis of
sugar-modified analogs of bredinin (mizoribine), a clinically useful
immnosuppressant, by a novel photochemical imidazole ring-cleavage
reaction as the key step. J. Chem.
Soc., Perkin Trans. 1., 2000,
3603-3609.
- ・M.
Sukeda, S. Shuto, I. Sugimoto, S. Ichikawa, A. Matsuda, Synthesis of
pyrimidine 2’-deoxy-ribonucleosides branched at the 2’-position via
radical atom-transfer cyclization reaction with a vinylsilyl group as a
radical-acceptor tether. J. Org.
Chem., 2000, 65, 8988-8996.
- ・
T. Kodama, M. Nomura, S. Shuto, A. Matsuda, Synthesis and radical reaction of 1’-phenylselenonucleosides. Nucleic Acids Symp. series, 2000, 44, 109-110.
- ・
M. Arisawa, C. Kato, H. Kaneko, A. Nishida, M. Nakagawa, Concise synthesis
of azacycloundecenes using ring-closing metathesis (RCM). J. Chem. Soc., Perkin Trans. 1, 2000, 1873-1876.
- ・
M. Arisawa, H. Kaneko, K. Yamaguchi, A. Nishida, M. Nakagawa,
Novel axially chiral macrolactam by Grubbs ring-closing metathesis (RCM). Synlett, 2000, 841-843.
- ・
M. Arisawa, M. Takahashi, E. Takezawa, T. Yamaguchi, Y. Torisawa, A. Nishida and M. Nakagawa,
Construction of chiral 1,2-cycloalkanopyrrolidines from L-proline using ring-closing metathesis (RCM). Chem. Pharm. Bull., 2000, 48, 1593-1596.
2001年
- ・T. Asai,
S. Shuto, A. Matsuda, T. Kakiuchi, H. Ohba, H. Tsukasa, N. Oku,
Targeted pulmonary cancer therapy by liposomal
5’-O-dipalmitoylphosphatidyl
2’-C-cyano-2’-deoxy-1-b-D-arabino-pentofuranosylcytosine. Cancer Lett., 2001, 162, 49-56.
- ・Y.
Kazuta, S. Shuto, H. Abe, A. Matsuda, The bisected s-trans
conformation-controlled highly stereoselective addition of Grignard
reagents to C-cyclopropylaldonitrone. An efficient synthesis of
1-phenyl-2-[(S)-1-aminoalkyl]-N,N-diethylcyclopropanecarboxamides, a
new class of potent NMDA receptor antagonists. J. Chem. Soc., Perkin Trans. 1., 2001, 599-604.
- ・T.
Kodama, S. Shuto, M. Nomura, A. Matsuda, 1’a-Branched-chain sugar
pyrimidine ribonucleosides from uridine. The first conversion of a
natural nucleoside into 1’-substituted ribonucleosides. Chem. Eur. J., 2001, 7, 2332-2340.
- ・S. Shuto,
M. Fukuoka, H. Abe, A. Matsuda, Intracellular Ca2+-mobilizing
adenine nucleotides. Synthesis and biological activity of cyclic
ADP-carbocyclic ribose and C-glycosidic analog of adenophostin A. Nucleosides Nucleotides, 2001, 20, 461-470.
- ・M.
Fukuoka, S. Shuto, Y, Ueno, A. Matsuda, Synthesis and biological
activities of cyclic ADP-carbocyclic-ribose and its analogs. Nucleosides Nucleotides, 2001, 20, 1355-1358.
- ・V.
Correa, E. P. Nerou, A. M. Riley, R. D. Marwood, S. Shuto, H. J.
Rosenberg, G. Horne, B. V. L. Potter, C. W. Taylor, Structural
determinants of adenophostin A activity at inositol trisphosphate
receptors. Mol. Pharmacol., 2001, 59, 1206-1215.
- ・R.
Tateoka, H. Abe, S. Miyauchi, S. Shuto, A. Matsuda, M. Kobayashi, K.
Miyazaki, N. Kamo, Significance of Substrate Hydrophobicity for
Recognition by an Oligopeptide Transporter (PEPT1). Bioconjugate Chem., 2001, 12, 485-492.
- ・S. Shuto,
G. Horne, R. D. Marwood, B. V. L. Potter, Total synthesis of nucleobase
modified adenophostin A mimics. Chem.
Eur. J., 2001, 7, 4937-4946.
- ・S. Shuto,
M. Fukuoka, A. Manikowsky, Y. Ueno, T. Nakano, R. Kuroda, H. Kuroda, A.
Matsuda, Total synthesis of cyclic ADP-carbocyclic-ribose, a stable
mimic of Ca2+-mobilizing second messenger cyclic ADP-ribose. J. Am. Chem. Soc., 2001, 123, 8750-8759.
- ・H. Abe,
S. Shuto, S. Tamura, A. Matsuda, An efficient method for preparing
fully O-silylated pyranoses conformationally restricted in the unusual
1C4-form. Tetrahedron Lett., 2001, 42, 6159-6161.
- ・H. Abe,
S. Shuto, A. Matsuda, Highly a- and b-selective radical C-glycosylation
reactions based on the conformational restriction strategy using a
controlling anomeric effect. A study on the conformation–anomeric
effect–stereoselectivity relationship in the anomeric radical
reactions. J. Am. Chem. Soc.,
2001, 123, 11870-11882.
- ・S.
Uchino, W. Watanabe, T. Nakamura, S. Shuto, Y. Kazuta, A. Matsuda, S.
Nakazima-Iijima, S. Kohsaka, Y. Kudo, M. Mishina, Inducible expression
of the four subtypes of N-methyl-D-aspartate receptor in CHO cells:
characterization of a novel NMDA receptor antagonist. PPDC. FEBS Lett., 2001, 506, 117-122.
- ・
M. Arisawa, N. G. Ramesh, M. Nakajima, H. Tohma, Y. Kita, Hypercalent iodine(III)
induced intramolecular cyclization of alpha-(Aryl)alkyl-beta-dicarbonyl compounds:
a convenient synthesis of benzannulated and spirobenzannulated compounds. J. Org. Chem., 2001, 66, 59-65.
- ・
H. Tohma, H. Morioka, S. Takizawa, M. Arisawa, Y. Kita, Efficient oxidative biaryl coupling reaction of phenol ether
derivatives using hypervalent iodine reagents. Tetrahedron, 2001, 57, 345-352.
- ・
Y. Iwata, M. Arisawa, R. Hamada, Y. Kita, Miho Y. Mizutani, N. Tomioka, A. Itai, S. Miyamoto,
Discovery of novel aldose reductase inhibitors using a protein structure-based approach:
3D-database search followed by design and synthesis. J. Med. Chem., 2001, 44, 1718-1728.
- ・
M. Arisawa, C. Theeraladanon, A. Nishida, M. Nakagawa, Synthesis of substituted 1,2-dihydroquinolines
and quinolines using ene-ene metathesis and ene-enol ether metathesis. Tetrahedron Lett., 2001, 42, 8029-8033.
2002年
- ・S.
Shuto, N. Minakawa, S. Niizuma, H-S. Kim, Y. Wataya, A. Matsuda, New
neplanocin analogs 12. An alternative synthesis and antimalarial effect
of (6’R)-6’-C-methylneplanocin A, a potent AdoHcy hydrolase inhibitor. J. Med. Chem., 2002, 45, 748-751.
- ・Y.
Kazuta, R. Tsujita, K. Ogawa, T. Hokonohara, K. Yamashita, K. Morino,
A. Matsuda, S. Shuto, Synthesis of
(1S,2R)-1-phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide
(PPDC) derivatives modified at the carbamoyl moiety as a new class of
NMDA receptor antagonists. Bioorg.
Med. Chem., 2002, 10, 1777-1791.
- ・Y.
Kazuta, A. Matsuda, S. Shuto, Development of versatile cis- and
trans-dicarbon-substituted chiral cyclopropane units. Synthesis of
(1S,2R)- and (1R,2R)-2-aminomethyl-1-(1H-imidazol-4-yl)cyclopropanes
and their enantiomers as conformationally restricted analogs of
histamine. J. Org. Chem. 2002, 67, 1669-1677.
- ・M.
Nomura, T. Sato, M. Washinosu, M. Tanaka, T. Asao, S. Shuto, A.
Matsuda, Practical large scale synthesis of
1-(3-C-ethynyl-b-D-ribo-furanosyl)cytosine (ECyd), a potent antitumor
nucleoside. Isobutyryloxy group as an efficient anomeric leaving group
in the Vorbrüggen glycosidation reaction. Tetrahedoron, 2002, 58, 1279-1288.
- ・S. Ono,
K. Ogawa, K. Yamashita, T. Yamamoto, Y. Kazuta, A. Matsuda, S. Shuto,
Conformational analysis of the NMDA receptor antagonist
(1S,2R)-1-Phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide
(PPDC) designed by a novel conformational restriction method based on
the structural feature of cyclopropane ring. Chem. Pharm. Bull., 2002, 50, 966-968.
- ・Y.
Kazuta, R. Tsujita, S. Uchino, N. Kamiyama, D. Mochizuki, K. Yamashita,
Y. Ohmori, A. Yamashita, T. Yamamoto, S. Kohsaka, A. Matsuda, S. Shuto,
Synthesis of
(1S,2R)-1-phenyl-2-[(S)-1-aminoalkyl]-N,N-diethylcyclopropanecarboxamides
as Novel NMDA Receptor Antagonists having a Unique NMDA Receptor
Subtypes Selectivity. J. Chem. Soc.,
Perkin Trans. 1, 2002,
1199-1212.
- ・A. H.
Guse, C. Cakir-Kiefer, M. Fukuoka, S. Shuto, K. Weber, A. Matsuda, G.
W. Mayer, N. Oppenheimer, F. Schuber, B. V. L. Potter, Novel
hydrolysis-resistant analogues of cyclic ADP-ribose: modification of
the “northern” ribose and calcium release activity. Biochemistry, 2002, 41, 6744-6751.
- ・T.
Kodama, S. Shuto, S. Ichikawa, A. Matsuda, A Highly Stereoselective
Samarium Diiodide-Promoted Aldol Reaction Using 1’-Phenylseleno-2’-Keto
Nucleosides. Synthesis of 1’a-Branched Uridine Derivatives. J. Org. Chem., 2002, 67, 7706-7715.
- ・T. Asai,
K. Shimizu, M. Kondo, K. Kuromi, K. Watanabe, K. Onigo, T. Taki, S.
Shuto, A. Matsuda, N. Oku, Anti-neovascular therapy by liposomal
DPP-CNDAC targeted to angiogenic vessels. FEBS Lett., 2002, 520, 167-170.
- ・N.
Atsumi, Y. Ueno, M. Kanazaki, S. Shuto, A. Matsuda, Thermal stability
of triplexes containing 4’a-C-aminoalkyl-2’-deoxynucleosides. Bioorg. Med. Chem., 2002, 10, 2933-2939.
- ・Y.
Kazuta, R. Tsujita, K. Yamashita, S. Uchino, S. Kohsaka, A. Matsuda, S.
Shuto, Synthesis of Derivatives of
(1S,2R)-1-Phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide
(PPDC) Modified at the 1-aromatic moiety as novel NMDA receptor
antagonists: the aromatic group is essential for the Activity. Bioorg. Med. Chem., 2002, 10, 3829-3848.
- ・M.
Sukeda, S. Ichikawa, A. Matsuda, and S. Shuto, A new entry to the
stereoselective introduction of an ethynyl group via radical reaction.
Synthesis of a potential antimetabolite 2’-deoxy-2'-C-ethynyluridine.
Angew. Chem. Int. Ed., 2002, 41, 4748-4750.
- ・
M. Yamanaka, M. Arisawa, A. Nishida, M. Nakagawa, An intriguing effect of Yb(OTf)3-TMSCl
in the halogenation of 1,1-disubstituted alkenes by NXS: selective synthesis of allyl halides. Tetrahedron Lett., 2002, 43, 2403-2406.
-
M. Arisawa, H. Kaneko, A. Nishida, M. Nakagawa, Stereoselectivity in ring-closing olefin metathesis (RCM)
of tethered di-hexenoyl derivatives. Perkin Trans. 1 , 2002, 959-964.
- ・
M. Arisawa, Y. Ando, M. Yamanaka, M. Nakagawa, A. Nishida, Novel synthetic method
for 2,3-dihydro-3-halo-3-methylindole from N-acetyl-2-isopropenylaniline by intramolecular haloamination. Synlett, 2002, 1514-1516.
- ・
M. Arisawa, S. Tsukamoto, M. Shimoda, M. Pristovsek, A. Nishida, Novel
organopalladium material formed on a sulfur-terminated GaAs(001). surface. Japanese Journal of Applied Physics, 2002, 41, L1197-1199.
- ・
M. Arisawa, Y. Terada, M. Nakagawa, A. Nishida, Selective isomerization of terminal
olefin catalyzed by a ruthenium complex: a novel indole synthesis via ring-closing metathesis (RCM). Angew. Chem. Int. Ed. Engl., 2002, 41, 4732-4734.
2003年
- ・A.
Tamura,
H. Abe, A. Matsuda, S. Shuto, Control of the a/b-stereoselectivity in
Lewis acid-promoted C-glycosidation using a controlling anomeric effect
based on the conformational restriction strategy. Angew. Chem. Int. Ed., 2003, 42, 1021-1023.
- ・L. Gan,
M. R. Seyedsayamdost, S. Shuto, A. Matsuda, G. A. Petsko, L. Headstrom,
The immunosuppressive agent mizoribine-monophosphate forms a transition
state analog complex with IMP dehydrogenase. Biochemistry, 2003, 42, 875-863.
- ・Y.
Kazuta, K. Hirano, K. Natsume, S. Yamada, R. Kimura, S. Matsumoto, K.
Furuichi, A. Matsuda, S. Shuto,
(1S,2S)-2-(2-Aminoethyl)-1-(1H-imidazol-4-yl)cyclopropane, a highly
selective agonist for the histamine H3 receptor, having a
cis-cyclopropane structure. ・J. Med.
Chem., 2003, 46, 1980-1988.
- ・M.
Sukeda, S. Ichikawa, A. Matsuda, S. Shuto, The first radical method for
the introduction of an ethynyl group using a silicon tether and its
application to the synthesis of 2’-deoxy-2'-C-ethynylnucleosides. J. Org. Chem., 2003, 68, 3465-3475.
- ・Y.
Kazuta, H. Abe, T. Yamamoto, A. Matsuda, S. Shuto, A systematic study
of the hydride reduction of cyclopropyl ketones with structurally
simplified substrates. Highly stereoselective reductions of
trans-substituted cyclopropyl ketones via the bisected
s-cis-conformation. J. Org. Chem.,
2003, 68, 3511-3521.
- ・M.
Nomura, S. Shuto, A. Matsuda, Synthesis of the cyclic and acyclic
acetal derivatives of 1-(3-C-ethynyl-b-D-ribo-pentofuranosyl)cytosine,
a potent antitumor nucleoside. Design of prodrugs to be selectively
activated in tumor tissues via the bio-reduction―hydrolysis mechanism. Bioorg. Med. Chem., 2003, 11, 2453-2461.
- ・H. Abe,
M. Terauchi, A. Matsuda, S. Shuto, A Study on the conformation–anomeric
effect–stereoselectivity relationship in anomeric radical reactions
using conformationally restricted glucose derivatives as substrates. J. Org. Chem., 2003, 68, 7439-7447.
- ・S. Shuto,
M. Fukuoka, T. Kudoh, C. Garnham, A. Galione, B. V. L. Potter, A.
Matsuda, Convergent Synthesis and Unexpected Ca2+-Mobilizing
Activity of 8-Substituted Analogues of Cyclic ADP-Carbocyclic-Ribose, a
Stable Mimic of the Ca2+-Mobilizing Second Messenger Cyclic ADP-Ribose.
J. Med. Chem., 2003, 46, 4741-4749.
- ・K.
Yamaguchi, Y. Kazuta, H. Abe, A. Matsuda, S. Shuto, Construction of a
cis-cyclopropane via reductive radical decarboxylation.
Enantioselective synthesis of cis- and
trans-1-arylpiperazyl-2-phenylcyclopropanes designed as
antidopaminergic agents. J. Org.
Chem., 2003, 68, 9255-9262.
- ・Y.
Ohmori, A. Yamashita, R. Tsujita, T. Yamamoto, K. Taniuchi, A. Matsuda,
S. Shuto, A method for designing conformationally restricted analogues
based on allylic strain: Synthesis of a novel class of noncompetitive
NMDA receptor antagonists having the acrylamide structure. J. Med. Chem., 2003, 46, 5326-5333.
- ・
M. Nakagawa, T. Nagata, K. Ono, H. Uchida, T. Watanabe, K. Hatakeyama, M. Akiba, M. Fuwa, M. Arisawa, A. Nishida,
Recent developments in marine indole alkaloid synthesis. Advances in Experimental Medicine and Biology, 2003, 527, 609-620.
- ・
M. Nakagawa, H. Uchida, K. Ono, Y. Kimura, M. Yamabe, T. Watanabe, R. Tsuji, M. Akiba,
Y. Terada, D. Nagaki, S. Ban, N. Miyashita, T. Kano, C. Theeraladanon, K. Hatakeyama, M. Arisawa,
A. Nishida, Practical synthesis of a 3, 4, 4a, 5, 8, 8a-hexahydro-2H-isoquinoline-1,6-dione ring system
by the Diels-Alder reaction of an optically active dienophile, a 5, 6-dihydro-1H-pyridin-2-one derivative, with Siloxydiene. Heterocycles , 2003, 59, 721-733.
2004年
- ・H. Dozol,
C. Maechling, R. Graf, A. Matsuda, S. Shuto, B. Spiess, Conformational
and inframolecular studies of the protonation of Adenophostin analogues
lacking the Adenine moiety. Biochim. Biophys. Acta-General Subjects, 2004, 1671, 1-8.
- ・Y.
Kazuta, H. Abe, T. Yamamoto, A. Matsuda, S. Shuto, The first
1,4-chelation-controlled nucleophilic addition to aldehydes with high
stereoselectivity. A systematic study of stereoselectivity in the
addition reaction of carbon nucleophiles to cis-substituted
cyclopropanecarbaldehydes. Tetrahedron,
2004, 60, 6689-6703.
- ・Y.
Yamamoto, S. Shuto, Y. Tamura, T. Kodam, S. Hoshika, S. Ichikawa, Y.
Ueno, E. Ohtsuka, Y. Komatsu, A. Matsuda, Oligodeoxynucleotides having
a loop consisting of 3’-deoxy-4’-C-(2-hydroxyethyl)thymidines form
stable hairpins. Biochemistry,
2004, 43, 8690-8699.
- ・M.
Terauchi, H. Abe, A. Matsuda, S. Shuto, An efficient synthesis of
b-C-glycosides based on the conformational restriction strategy: Lewis
acid-promoted silane reduction of the anomeric position with complete
stereoselectivity. Org. Lett.,
2004, 6, 3751-3754.
- ・Y.
Kazuta, H. Abe, A. Matsuda, S. Shuto, Highly stereoselective Grignard
addition to cis-substituted C-cyclopropylaldonitrones. The bisected
s-trans transition state can be stabilized effectively by the Lewis
acid-coordination. J. Org. Chem.,
2004, 69, 9143-9150.
- ・
C. Theeraladanon, M. Arisawa, A. Nishida, M. Nakagawa, A novel synthesis
of substituted quinolines using ring-closing metathesis (RCM): its application to
the synthesis of key intermediates for anti-malarial agents. Tetrahedron, 2004, 60, 3017-3035.
- ・
Y. Terada, M. Arisawa, A. Nishida, Cycloisomerization promoted by the combination of a
ruthenium carbene catalyst and vinyloxytrimethylsilane, and its application to the synthesis
of heterocyclic compounds: 3-methylene-2,3-dihydroindoles and 3-methylene-2,3-dihydrobenzofurans. Angew. Chem. Int. Ed. Engl. , 2004, 43, 4063-4067.
- ・
I. Takamiya, S. Tsukamoto, M. Shimoda, N. Miyashita, M. Arisawa, Y. Arakawa, Atsushi Nishida,
Novel palladium catalyst supported on GaAs(001) passivated by ammonium sulfide. Chem. Lett., 2004, 33, 1208-1209.
2005年
- ・C.
Takagi, M. Sukeda, H.-S. Kim, Y. Wataya, S. Yabe, Y. Kitade, A.
Matsuda, S. Shuto, Synthesis of 5’-methylenearisteromycin and its
2-fluoro congener with potent antimalarial activity due to inhibition
of the parasite S-sdenosylhomocysteine hydrolase. Org. Biomol. Chem., 2005, 3, 1245-1251.
- ・M.
Terauchi, Y. Yahiro, H. Abe, S. Ichikawa, S. C. Tovey, S. G. Dedos,
C.W. Taylor, B.V. L. Potter, A. Matsuda, S. Shuto, Synthesis of
4,8-anhydro-D-glycero-D-ido-nonanitol 1,6,7-trisphosphate as a novel
IP3 receptor ligand using a stereoselective radical cyclization
reaction based on a conformational restriction strategy. Tetrahedron, 2005, 61, 3697-3707.
- ・M.
Hashii, S. Shuto, M. Fukuoka, T. Kudoh, A. Matsuda, H. Higashida,
Amplification of depolarization-induced and ryanodine-sensitive
cytosolic Ca2+ elevation by synthetic carbocyclic analogues of cyclic
ADP-ribose and their antagonistic effects in NG108-15 neuronal cells. J. Neurochem.,
2005, 94, 316-323.
- ・T. Kudoh,
M. Fukuoka, S. Ichikawa, T. Murayama, Y. Ogawa, M. Hashii, H.
Higashida, S. Kunerth, K. Weber, A. H. Guse, B. V. L. Potter, A.
Matsuda, S. Shuto , Synthesis of stable and cell-type selective
analogues of cyclic ADP-ribose, a Ca2+-mobilizing second messenger.
Structure-activity relationship of the N1-ribose moiety. J. Am. Chem. Soc., 2005, 127, 8846-8825.
- ・
M. Sukeda, A. Matsuda, S. Shuto, Radical hydrogen abstraction?cyclization with
a 2-bromovinylsilyl group as a bifunctional tether. Tetrahedron, 2005, 61, 7865-7873.
- ・
M. Terauchi, A. Matsuda, S. Shuto, Efficient synthesis of b-C-glucosides via radical cyclization with
a silicon tether based on the conformational restriction strategy. Tetrahedron Lett., 2005, 46, 6555-6558.
- ・
T. Kudoh, M. Fukuoka, S. Shuto, A. Matsuda, Synthesis biological activity of cyclic ADP-carbocyclic-ribose analogs:
Structure-activity relationship and conformational analysis of the N1-carbocyclic-ribose moiety.Nucleosides, Nucleotides, and Nucleic Acids, 2005, 24, 655-658.
- ・
C. Theeraladanon, M. Arisawa, M. Nakagawa, A. Nishida,
Total synthesis of (+)-(S)-angustureine and determination of the absolute configuration of the natural product angustureine., 2005, 16, 827-831.
- ・
M. Arisawa, C. Theeraladanon, A. Nishida, Preparation of N-sulfonyl-quinoline using ring-closing metathesis (RCM). Heterocycle, 2005, 66, 683-688.
2006年
- ・
M. Terauchi, H. Abe, S. C. Tovey, S. G. Dedos, C. W. Taylor, M. Paul, M. Trusselle, B. V. L. Potter, A. Matsuda, S. Shuto, A systematic study
of C-glucoside trisphosphates as myo-inositol trrisphosphate receptor ligands. Synthesis of b-C-glucoside trisphosphates
based on the conformational restriction strategy. J. Med. Chem., 2006, 49, 1900-1909.
- ・
T. Mochizuki, Y. Kondo, H. Abe, C. W. Taylor, B. L. V. Potter, A. Matsuda, S. Shuto,
Design and synthesis of 5’-deoxy-5’-phenyadenophostin A, a highly potent IP3 receptor ligand. Org. Lett., 2006, 8, 1455-1458.
- ・
S. Ichikawa, N. Minakawa, S. Shuto, M. Tanaka, T. Sasaki, A. Matsuda,
Synthesis of 3-b-carbamoylmethylcytidine (CAMC) and its derivatives as potential antitumor agents. Org. Biomol. Chem., 2006, 4, 1284-1296.
- ・
T. Kudoh, T. Maruyama, Y. Ogawa, A. Matsuda, S. Shuto, Synthesis of cyclic ADP-carbocyclic ?xylose and
its 3”-O-methyl analogue as stable and potent Ca2+-mobilizing agents.Nucleosides, Nucleotides, Nucleic Acids, 2006, 25, 583-599.
- ・
T. Kodama, S. Shuto, A. Matsuda, Synthesis of pyrimidine 1’-fluoronucleosides. Tetrahedron Lett., 2006, 48, 4429-4432.
- ・
N. Sakaguchi, S. Hirano, A. Matsuda, S. Shuto, The radical reactions with 2-bromobenzylidene group,
a protecting/radical-translocating group for the 1.6-radical hydrogen transfer reaction. Org. Lett., 2006, 8, 3291-3294.
- ・
Y. Terada, M. Arisawa, A. Nishida, Synthesis of the putatice structure of fistulosin using the ruthenium-catalyzed cycloisomerization of diene. J. Org. Chem., 2006, 71, 1269-1272.
- ・
M. Arisawa, Y. Terada, K. Takahashi, M. Nakagawa, A. Nishida,
Development of isomerization and cycloisomerization with use of a ruthenium hydride
with N-heterocyclic carbene and its application to the synthesis of heterocycles. J. Org. Chem., 2006, 71, 4255-4261.
- ・
I. Takamiya, S. Tsukamoto, M. Shimoda, M. Arisawa, A. Nishida, Y. Arakawa,
Highly reactive organopalladium catalyst formed on sulfur-terminated GaAs(001)-(2 X 6) surface. Japanese Journal of Applied Physics, 2006, 45, L475-477.
- ・
M. Arisawa, M. Hamada, I. Takamiya, M. Shimoda, S. Tsukamoto, Y. Arakawa, A. Nishida,
Development of a method for preparing a highly reactive and stable, recyclable and
environmentally benign organopalladium catalyst supported on sulfur-terminated gallium arsenide (001):
a three-component catalyst, {Pd}-S-GaAs (001), and its properties. Adv. Synth. Cat., 2006, 348, 1063-1070.
- ・
T. Kodama, A. Matsuda, S. Shuto, Synthesis of 1’-fluorouracil nucleosides as potential antimetabolites. Tetrahedron, 2006, 62, 10011-10017.
- ・
M. Watanabe, Y. Kazuta, H. Hayashi, S. Yamada, A. Matsuda, S. Shuto,
The stereochemical diversity-oriented conformational restriction strategy.
Development of potent histamine H3 and/or H4 receptor antagonists with an imidazolylcyclopropane structure. J. Med. Chem., 2006, 49, 5587-5596.
- ・
T. Mochizuki, Y. Kondo, H. Abe, S. C. Tovey, S. G. Dedos, C. W. Taylor, M. Paul, B. V. L. Potter, A. Matsuda, S. Shuto,
Synthesis of adenophostin A analogues conjugating an aromatic group at the 5’-position as potent IP3 receptor ligands. J. Med. Chem., 2006, 49, 5750-5758.
2007年
- ・
T. Kudoh, T. Murayama, A. Matsuda, S. Shuto, Substitution at the 8-position of 3"-deoxy-cyclic ADP-carbocyclic-ribose, a highly potent Ca2+-mobilizing agent, provides partial agonist. Bioorg. Med. Chem., 2007, 15, 3032-3040.
- ・
D. Jin, H-X. Liu, O. Lopatina, M. Hashii, S. Amina, S. Shuto, Y. Shiraishi, S. Tanaka, H. Higashida, Oxytocin released from mouse hypothalamus and nerve endings by extracellular applicaion of beta-NAD+ and cyclic ADP-ribose. Nature Protocol, 2007, DOI 10.1038/nprot.2007.214. (http://www.natureprotocols.com/2007/04/18/oxytocin_released_from_mouse_h.php)
- ・
S. Shuto, Design, synthesis, and biological activity of carbocyclic analogues of cyclic ADP-ribose, a Ca2+-mobilizing second messenger, Nucleic Acids Symposium Series, 2007, 51, 109-110.
- ・
M. Arisawa, Development of environmentally benign organometallic catalysis for drug discovery and its application, Chem. Pharm. Bull. 2007, 55, 1099-1118.
- ・
M. Arisawa, Y. Terada, K. Takahashi, M. Nakagawa, A. Nishida, Chem. Rec. 2007, 7, 238-253.
2008年
- ・
T. Asai, S. Miyazawa, N. Maeda, K. Hatanaka, Y. Katanasaka, K. Shimizu, S. Shuto, N. Oku, Antineovascular therapy with angiogenic vessel-targeted polyethyleneglycol-shielded liposomal DPP-CNDAC, Cancer Sci., 2008, 99, 1029-1033.
- ・
N. Sakaguchi, T. Kudoh, T. Tsuzuki, T. Murayama, T. Sakurai, A. Matsuda, M. Arisawa, S. Shuto, Synthesis of 5”-branched derivatives of cyclic ADP-carbocyclic-ribose, a potent Ca2+-mobilizing agent: the first antagonists modified at the N1-ribose moiety, Bioorg. Med. Chem. Lett., 2008, 18, 3814-3818.
- ・
T. Kudoh, K. Weber, A. H. Guse, B. V. L. Potter, M. Hashii, H. Higashida, M. Arisawa, A. Matsuda, S. Shuto, Design and synthesis of 4”,6”-unsaturated cyclic ADP-carbocyclic ribose as a Ca2+-mobilizing agent, Tetrahedron Lett., 2008, 49, 3976-3979.
- ・
K. Yoshida, K. Yamaguchi, T. Sone, Y. Unno, A. Asai, H. Yokosawa, A. Matsuda, M. Arisawa, S. Shuto. Synthesis of 2,3- and 3,4-methanoamino scid equivalents with stereochemical diversity and their conversion into the tripeptide proteasome inhibitor belactosin A and its highly potent cis-cyclopropane stereoisomer. Org. Lett., 2008, 10, 3571-3574.
- ・
T. Kudoh, K. T. Murayama, M. Hashii, H. Higashida, T. Sakurai, C. Maechling, B. Spiess, K. Weber, A. H. Guse, B. V. L. Potter, M. Arisawa, A. Matsuda, S. Shuto, Design and synthesis of 4”,6”-unsaturated cyclic ADP-carbocyclic ribose, a Ca2+-mobilizing agent selectively active in T cells. Tetrahedron, 2008, 64, 9754-9765.
- ・
K. Yamaguchi, Y. Kazuta, K. Hirano, S. Yamada, A. Matsuda, S. Shuto, Synthesis of 1-arylpiperazyl-2-phenylcyclopropanes designed as antidopaminergic agents. cyclopropane-based conformationally restricted analogs of haloperidol. Bioorg. Med. Chem., 2008, 16, 8875-8881.
- ・
R. M. Gulman, M. Hamada, I. Takamiya, M. Shimoda, S. Shuto, A. Nishida, S. Tsukamoto, M. Arisawa, Preparation of tethered palladium catalysis supported on gold(111) and its surface characterization by X-ray photoelectron spectroscopy. Chem. Bul. Soc. Jp., 2008, 81, 1012-1018.
- ・
K. Kaziwara, M. Arisawa, S. Shuto, A method for cleaving an allyl protecting group at the amide nitrogen of peptides by one-pot olefin isomerization-oxidation. J. Org. Chem., 2008, 73, 9494-9496.
その他の総説等
- ・周東 智,
シクロプロパン環の構造特性に基づく配座制御法の開発とN-メチル-D-アスパラギン酸(NMDA)受容体探索分子創製への応用. 薬学研究の進歩, 2000, 16, 43-54.
- ・周東 智,
福岡正哲, 松田 彰, 新しいセカンドメッセンジャー・サイクリックADP-リボース(cADPR)とその誘導体の化学, 有合化, 2000, 58, 1144-1154.
- ・
T. Kodama, M. Nomura, S. Shuto, A. Matsuda, Synthesis and radical reaction of
1’-phenylselenonucleosides.Nucleic Acids Symp. series, 2000, 44, 109-110.
- ・
M. Arisawa, H. Tohma, Y. Kita, Development of intramolecular oxidative phenolic
coupling reactions using hypervalent iodine(III) reagents and their application to the
synthesis of Amaryllidaceae alkaoids.Yakugaku Zasshi , 2000, 120, 1061-1073.
- ・
M. Arisawa, Synthesis of 1,2-diols using axial chirality. Farumacia, 2000, 36, 226.
- ・
M. Arisawa, Ruthenium. Farumacia, 2000, 36, 626-627.
- ・S. Shuto,
K. Yoshii, A. Matsuda,
(1S,2R)-1-Phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide
(PPDC), a new class of NMDA receptor antagonists. Molecular design by a
novel conformational restriction strategy. Jpn. J. Pharmacol., 2001, 85, 207-213.
- ・周東 智, 杉本 勇, 松田 彰, ビニルシリル基をテザーに用いるラジカル反応:C2ユニットの立体選択的導入法の開発と5配位ケイ素ラジカル遷移状態を経由する新規ラジカル環拡大反応.有合化, 2001, 59, 589-598.
- ・
S. Shuto, T. Kudoh, M. Fukuoka, Y. Ueno, A. Matsuda, Synthesis and biological activity
of cyclic ADP-carbocyclic-ribose and its analogs as stable mimics of Ca2+-mobilizing
second messenger cyclic ADP-ribose.Nucleic Acids Res. Supplemen, 2001, 1, 5-6.
- ・
西田篤司, 有澤光弘, 新たな抗マラリア薬の創製.千葉日報, 2001, 12月12日
- ・周東 智,
Ca2+動員を介する細胞内情報伝達系を標的とする機能性分子の創製. 化学工業, 2002, 53, 353-358.
- ・S. Shuto, M. Kanazaki, I. Sugimoto, S. Ichikawa, Y. Nagasawa, Y. Ueno, H. Abe, N.
Minakawa, M. Sukeda, T. Kodama, M. Nomura, A. Matsuda, Development of
new radical reactions with a vinylsilyl group and their application to
the synthesis of branched-chain sugar nucleosides. Recent Advances in
Nucleosides: Chemistry and Chemotherapy, Ed. by C. K. Chu, Elsevier Science: Amsterdam, 2002. 21-55.
- ・
S. Shuto, T. Mochizuki, H. Abe, Y. Kondo, A. Matsuda, Synthesis and biological activity
of adenophostin derivatives as IP3 receptor ligands.Nucleic Acids Res. Supplement., 2002, 2, 23-24.
- ・周東 智,
汎用性キラルシクロプロパンユニットの開発とそのヒスタミンH3サブタイプ特異的アゴニスト創製への応用. Medchem News, 2003, 13, No. 4, 21-25.
- ・S. Shuto,
A. Matsuda, Chemistry of cyclic ADP-ribose and its analogs. Curr. Med. Chem., 2005, 11, 827-845.
- ・周東 智,
松田 彰, 創薬:オングストロムの分子設計. “ナノバイオエンジニアリング,
化学フロンティア13”, 杉本直己偏, 2004,
pp37-49.
- ・
S. Shuto, Y. Tamura, Y. Yamamoto, T. Kodama, S. Hoshika, S. Ichikawa, Y. Ueno, E. Ohtsuka,
Y. Komatsu, A. Matsuda, Stable hairpins having a loop consisting of 3’-deoxy-4’-C-(2-hydroxyethyl)thymidines. Nucleic Acids Res. Supplement., 2004, 4, 66-67.
- ・
寺田幸芳,有澤光弘,西田篤司,有機金属触媒を用いるα, ωジエンの環化異性化反応 Chemical Times, 2004, 194(4), 2-10(review).
- ・
有澤光弘,西田篤司,新規生物活性複素環合成法の開発 化学工業, 2004, 55, 120-123.
- ・
T. Kudoh, T. Maruyama, A. Matsuda, S. Shuto, Synthesis and biological activity
of 4”,6”-unsaturated cyclic ADP-carbocyclic-ribose. Nucleic Acids Symposium Serie, 2005, 49, 25-26.
- ・
M. Arisawa, Y. Terada, K. Takahashi, M. Nakagawa, A. Nishida,
Development of novel reactions using ruthenium carbene catalyst and its application to
novel preparative methoeds for nitrogen-containing heterocycles. J. Organometallic Chem., 2005, 690, 5398-5406.
- ・
T. Kodama, A. Matsuda, S. Shuto, The first synthesis of 1'-fluoronucleosides. Nucleic Acids Symp. Ser., 2006, 50, 3-4.
- ・
S. Sakaguchi, T. Kudoh, T. Murayama, M. Arisawa, A. Matsuda, S. Shuto, Synthesis of 5''-substituted cyclic ADP-carbocyclic-ribose as biological tools. Nucleic Acids Symp. Ser., 2006, 50, 119-120.
- ・
有澤光弘, マット・シャー研へようこそ 化学, 2006, 50-53
- ・
M. Arisawa, A. Nishida, M. Nakagawa, Preparation of nitrogen-containing heterocycles using ring-closing metathesis
(RCM) and its application to natural product synthesis. J. Organomet. Chem., 2006, 691, 5109-5121.
- ・
M. Arisawa, Development of environmentally benign organometallic catalysis for drug discovery and its application. Chem. Pharm. Bull., 2007, 55, 1099-1118.
- ・
周東 智, 創薬化学からミゾリビンを考える:ミゾリビンリン酸はIMPDHの遷移状態模倣型阻害剤である, 炎症と免疫, 2007, 15, 135-141.
- ・
周東 智, 市川 聡, 阿部 洋, 松田 彰, ピラノース配座制御に基づく立体選択的グリコシル化反応, 有合化, 2008, 66, 52-61
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