Synthesis of phenylalkyl-substituted polyhydroxypiperidines as potent inhibitors for α-l-fucosidase

Tomoki Saka; Toru Okaki; Shohei Ifuku; Yukiko Yamashita; Kasumi Sato; Shota Miyawaki; Akiko Kamori; Atsushi Kato; Isao Adachi; Yasuhiro Tezuka; Peter G. Kiria; Osamu Onomura; Daishiro Minato; Kenji Sugimoto; Yuji Matsuya; Naoki Toyooka

doi:10.1016/j.tet.2013.10.006

Synthesis of phenylalkyl-substituted polyhydroxypiperidines as potent inhibitors for α-l-fucosidase

Tomoki Saka, Toru Okaki, Shohei Ifuku, Yukiko Yamashita, Kasumi Sato, Shota Miyawaki, Akiko Kamori, Atsushi Kato^*, Isao Adachi, Yasuhiro Tezuka, Peter G. Kiria, Osamu Onomura, Daishiro Minato, Kenji Sugimoto, Yuji Matsuya, Naoki Toyooka

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Synthesis and inhibitory activities against α-l-fucosidase of phenylalkyl-substituted polyhydroxypiperidines have been described. Among the newly synthesized compounds, 2,4,6-trichloro derivative (16q) showed very high inhibitory activity against α-l-fucosidase with IC₅₀ value of 0.005 μM, and K_i values of 0.0011 μM, respectively.

Original language	English
Pages (from-to)	10653-10661
Number of pages	9
Journal	Tetrahedron
Volume	69
Issue number	49
DOIs	https://doi.org/10.1016/j.tet.2013.10.006
State	Published - 2013/12/09

Keywords

C-1 phenylalkyl-substituted polyhydroxypiperidine
Iminosugar
l-Fucose
α-l-fucosidase

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2013.10.006

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Saka, T., Okaki, T., Ifuku, S., Yamashita, Y., Sato, K., Miyawaki, S., Kamori, A., Kato, A., Adachi, I., Tezuka, Y., Kiria, P. G., Onomura, O., Minato, D., Sugimoto, K., Matsuya, Y., & Toyooka, N. (2013). Synthesis of phenylalkyl-substituted polyhydroxypiperidines as potent inhibitors for α-l-fucosidase. Tetrahedron, 69(49), 10653-10661. https://doi.org/10.1016/j.tet.2013.10.006

@article{7c123d2d99cc4d1d898c09f78d7babda,

title = "Synthesis of phenylalkyl-substituted polyhydroxypiperidines as potent inhibitors for α-l-fucosidase",

abstract = "Synthesis and inhibitory activities against α-l-fucosidase of phenylalkyl-substituted polyhydroxypiperidines have been described. Among the newly synthesized compounds, 2,4,6-trichloro derivative (16q) showed very high inhibitory activity against α-l-fucosidase with IC50 value of 0.005 μM, and Ki values of 0.0011 μM, respectively.",

keywords = "C-1 phenylalkyl-substituted polyhydroxypiperidine, Iminosugar, l-Fucose, α-l-fucosidase",

author = "Tomoki Saka and Toru Okaki and Shohei Ifuku and Yukiko Yamashita and Kasumi Sato and Shota Miyawaki and Akiko Kamori and Atsushi Kato and Isao Adachi and Yasuhiro Tezuka and Kiria, {Peter G.} and Osamu Onomura and Daishiro Minato and Kenji Sugimoto and Yuji Matsuya and Naoki Toyooka",

note = "Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research (C) (N.T.) from Japan Society for the Promotion of Science (JSPS). The authors thank to Dr. Ralph A. Saporito, John Carroll University, for English editions. ",

year = "2013",

month = dec,

day = "9",

doi = "10.1016/j.tet.2013.10.006",

language = "英語",

volume = "69",

pages = "10653--10661",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "49",

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Saka, T, Okaki, T, Ifuku, S, Yamashita, Y, Sato, K, Miyawaki, S, Kamori, A, Kato, A, Adachi, I, Tezuka, Y, Kiria, PG, Onomura, O, Minato, D, Sugimoto, K, Matsuya, Y & Toyooka, N 2013, 'Synthesis of phenylalkyl-substituted polyhydroxypiperidines as potent inhibitors for α-l-fucosidase', Tetrahedron, vol. 69, no. 49, pp. 10653-10661. https://doi.org/10.1016/j.tet.2013.10.006

TY - JOUR

T1 - Synthesis of phenylalkyl-substituted polyhydroxypiperidines as potent inhibitors for α-l-fucosidase

AU - Saka, Tomoki

AU - Okaki, Toru

AU - Ifuku, Shohei

AU - Yamashita, Yukiko

AU - Sato, Kasumi

AU - Miyawaki, Shota

AU - Kamori, Akiko

AU - Kato, Atsushi

AU - Adachi, Isao

AU - Tezuka, Yasuhiro

AU - Kiria, Peter G.

AU - Onomura, Osamu

AU - Minato, Daishiro

AU - Sugimoto, Kenji

AU - Matsuya, Yuji

AU - Toyooka, Naoki

N1 - Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research (C) (N.T.) from Japan Society for the Promotion of Science (JSPS). The authors thank to Dr. Ralph A. Saporito, John Carroll University, for English editions.

PY - 2013/12/9

Y1 - 2013/12/9

N2 - Synthesis and inhibitory activities against α-l-fucosidase of phenylalkyl-substituted polyhydroxypiperidines have been described. Among the newly synthesized compounds, 2,4,6-trichloro derivative (16q) showed very high inhibitory activity against α-l-fucosidase with IC50 value of 0.005 μM, and Ki values of 0.0011 μM, respectively.

AB - Synthesis and inhibitory activities against α-l-fucosidase of phenylalkyl-substituted polyhydroxypiperidines have been described. Among the newly synthesized compounds, 2,4,6-trichloro derivative (16q) showed very high inhibitory activity against α-l-fucosidase with IC50 value of 0.005 μM, and Ki values of 0.0011 μM, respectively.

KW - C-1 phenylalkyl-substituted polyhydroxypiperidine

KW - Iminosugar

KW - l-Fucose

KW - α-l-fucosidase

UR - http://www.scopus.com/inward/record.url?scp=84887409549&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2013.10.006

DO - 10.1016/j.tet.2013.10.006

M3 - 学術論文

AN - SCOPUS:84887409549

SN - 0040-4020

VL - 69

SP - 10653

EP - 10661

JO - Tetrahedron

JF - Tetrahedron

IS - 49

ER -

Synthesis of phenylalkyl-substituted polyhydroxypiperidines as potent inhibitors for α-l-fucosidase

Abstract

Keywords

ASJC Scopus subject areas

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