Design and synthesis of N–acetylglucosamine derived 5a-carbasugar analogues as glycosidase inhibitors

Chintam Narayana; Priti Kumari; Daisuke Ide; Nasako Hoshino; Atsushi Kato; Ram Sagar

doi:10.1016/j.tet.2018.02.063

Design and synthesis of N–acetylglucosamine derived 5a-carbasugar analogues as glycosidase inhibitors

Chintam Narayana, Priti Kumari, Daisuke Ide, Nasako Hoshino, Atsushi Kato, Ram Sagar^*

^*この論文の責任著者

薬剤部

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

10 被引用数 (Scopus)

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An efficient synthesis of new six-membered carbasugars in both L-form and D-form starting from N–acetylglucosamine is described. The key synthetic steps involved regioselective protection and deprotection, Ferrier carbocyclization, Peterson olefination, hydroboration and stereoselective epoxidation followed by regioselective epoxide ring opening reactions. These six-membered carbasugars showed moderate glycosidase inhibitory activity and one of the compounds was found selective towards β-galactosidase inhibitory activity.

本文言語	英語
ページ（範囲）	1957-1964
ページ数	8
ジャーナル	Tetrahedron
巻	74
号	15
DOI	https://doi.org/10.1016/j.tet.2018.02.063
出版ステータス	出版済み - 2018/04/12

ASJC Scopus 主題領域

生化学
創薬
有機化学

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10.1016/j.tet.2018.02.063

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title = "Design and synthesis of N–acetylglucosamine derived 5a-carbasugar analogues as glycosidase inhibitors",

abstract = "An efficient synthesis of new six-membered carbasugars in both L-form and D-form starting from N–acetylglucosamine is described. The key synthetic steps involved regioselective protection and deprotection, Ferrier carbocyclization, Peterson olefination, hydroboration and stereoselective epoxidation followed by regioselective epoxide ring opening reactions. These six-membered carbasugars showed moderate glycosidase inhibitory activity and one of the compounds was found selective towards β-galactosidase inhibitory activity.",

keywords = "Carbasugar, Ferrier carbocyclization, Glycosidase inhibitors, N-acetyl glucosamine, Peterson olefination",

author = "Chintam Narayana and Priti Kumari and Daisuke Ide and Nasako Hoshino and Atsushi Kato and Ram Sagar",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

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day = "12",

doi = "10.1016/j.tet.2018.02.063",

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T1 - Design and synthesis of N–acetylglucosamine derived 5a-carbasugar analogues as glycosidase inhibitors

AU - Narayana, Chintam

AU - Kumari, Priti

AU - Ide, Daisuke

AU - Hoshino, Nasako

AU - Kato, Atsushi

AU - Sagar, Ram

PY - 2018/4/12

Y1 - 2018/4/12

N2 - An efficient synthesis of new six-membered carbasugars in both L-form and D-form starting from N–acetylglucosamine is described. The key synthetic steps involved regioselective protection and deprotection, Ferrier carbocyclization, Peterson olefination, hydroboration and stereoselective epoxidation followed by regioselective epoxide ring opening reactions. These six-membered carbasugars showed moderate glycosidase inhibitory activity and one of the compounds was found selective towards β-galactosidase inhibitory activity.

AB - An efficient synthesis of new six-membered carbasugars in both L-form and D-form starting from N–acetylglucosamine is described. The key synthetic steps involved regioselective protection and deprotection, Ferrier carbocyclization, Peterson olefination, hydroboration and stereoselective epoxidation followed by regioselective epoxide ring opening reactions. These six-membered carbasugars showed moderate glycosidase inhibitory activity and one of the compounds was found selective towards β-galactosidase inhibitory activity.

KW - Carbasugar

KW - Ferrier carbocyclization

KW - Glycosidase inhibitors

KW - N-acetyl glucosamine

KW - Peterson olefination

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DO - 10.1016/j.tet.2018.02.063

M3 - 学術論文

AN - SCOPUS:85043326542

SN - 0040-4020

VL - 74

SP - 1957

EP - 1964

JO - Tetrahedron

JF - Tetrahedron

IS - 15

ER -

Design and synthesis of N–acetylglucosamine derived 5a-carbasugar analogues as glycosidase inhibitors

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