Enantiodivergent strategy for the synthesis of polyhydroxylated pyrrolizidines and evaluation of their inhibitory activities against glycosidases

Daisuke Minehira; Takuya Okada; Ren Iwaki; Atsushi Kato; Isao Adachi; Naoki Toyooka

doi:10.1016/j.tetlet.2014.11.087

Enantiodivergent strategy for the synthesis of polyhydroxylated pyrrolizidines and evaluation of their inhibitory activities against glycosidases

Daisuke Minehira^*, Takuya Okada, Ren Iwaki, Atsushi Kato, Isao Adachi, Naoki Toyooka^*

^*この論文の責任著者

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

4 被引用数 (Scopus)

抄録

The enantiodivergent synthesis of polyhydroxylated pyrrolizidines has been achieved, starting from common intermediate 1. The synthesis involved the stereoselective construction of the pyrrolizidine core unit by using intramolecular Michael cyclization reaction as the key reaction. The synthesized eight isomers were evaluated for various glycosidase inhibition effects. Compound 15 showed a moderate inhibitory activity against α-l-fucosidase and a high selectivity compared from the other glycosidases.

本文言語	英語
ページ（範囲）	331-334
ページ数	4
ジャーナル	Tetrahedron Letters
巻	56
号	2
DOI	https://doi.org/10.1016/j.tetlet.2014.11.087
出版ステータス	出版済み - 2015/01/08

ASJC Scopus 主題領域

生化学
創薬
有機化学

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10.1016/j.tetlet.2014.11.087

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引用スタイル

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title = "Enantiodivergent strategy for the synthesis of polyhydroxylated pyrrolizidines and evaluation of their inhibitory activities against glycosidases",

abstract = "The enantiodivergent synthesis of polyhydroxylated pyrrolizidines has been achieved, starting from common intermediate 1. The synthesis involved the stereoselective construction of the pyrrolizidine core unit by using intramolecular Michael cyclization reaction as the key reaction. The synthesized eight isomers were evaluated for various glycosidase inhibition effects. Compound 15 showed a moderate inhibitory activity against α-l-fucosidase and a high selectivity compared from the other glycosidases.",

keywords = "Enantiodivergent strategy, Glycosidase, Hyacinthacine, Imino sugar, Pyrrolizidine",

author = "Daisuke Minehira and Takuya Okada and Ren Iwaki and Atsushi Kato and Isao Adachi and Naoki Toyooka",

note = "Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd.",

year = "2015",

month = jan,

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doi = "10.1016/j.tetlet.2014.11.087",

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T1 - Enantiodivergent strategy for the synthesis of polyhydroxylated pyrrolizidines and evaluation of their inhibitory activities against glycosidases

AU - Minehira, Daisuke

AU - Okada, Takuya

AU - Iwaki, Ren

AU - Kato, Atsushi

AU - Adachi, Isao

AU - Toyooka, Naoki

PY - 2015/1/8

Y1 - 2015/1/8

N2 - The enantiodivergent synthesis of polyhydroxylated pyrrolizidines has been achieved, starting from common intermediate 1. The synthesis involved the stereoselective construction of the pyrrolizidine core unit by using intramolecular Michael cyclization reaction as the key reaction. The synthesized eight isomers were evaluated for various glycosidase inhibition effects. Compound 15 showed a moderate inhibitory activity against α-l-fucosidase and a high selectivity compared from the other glycosidases.

AB - The enantiodivergent synthesis of polyhydroxylated pyrrolizidines has been achieved, starting from common intermediate 1. The synthesis involved the stereoselective construction of the pyrrolizidine core unit by using intramolecular Michael cyclization reaction as the key reaction. The synthesized eight isomers were evaluated for various glycosidase inhibition effects. Compound 15 showed a moderate inhibitory activity against α-l-fucosidase and a high selectivity compared from the other glycosidases.

KW - Enantiodivergent strategy

KW - Glycosidase

KW - Hyacinthacine

KW - Imino sugar

KW - Pyrrolizidine

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DO - 10.1016/j.tetlet.2014.11.087

M3 - 学術論文

AN - SCOPUS:84922261762

SN - 0040-4039

VL - 56

SP - 331

EP - 334

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 2

ER -