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タイトル(別表記) Synthetic studies of ancistrocladinium A and B, antileishmanial compounds isolated from a Congolese Ancistrocladus Species
フルテキストURL srfa_108_001_004.pdf
著者 清田 洋正| 齋藤 昭人| 高井 桃子| 桑原 重文|
抄録 Synthetic studies of ancistrocladinium A and B, antileishmanial compounds isolated from a Congolese Ancistrocladus sp., are described. Buchwald‒Hartwig coupling reaction between the dihydroisoquinoline and the naphthyl triflate failed. The main framework of ancistrocladinium A was constructed by 1,2‒addition of the amine to the naphthoquinone in the presence of celium trichloride as a catalyst. On the other hand, 1,4‒addition of the amine to the naphthoquinone proceeded without catalyst to form the framework of B. These products will be valuable leads for antileishmanial agents.
キーワード ancistrocladinium A and B synthetic studies leishmania, Ancistrocladus isoquinoline
備考 原著論文 (Original paper)
出版物タイトル 岡山大学農学部学術報告
発行日 2019-02-01
108巻
出版者 岡山大学農学部
出版者(別表記) The Faculty of Agriculture, Okayama University
開始ページ 1
終了ページ 4
ISSN 2186-7755
資料タイプ 紀要論文
言語 Japanese
論文のバージョン publisher
Eprints Journal Name srfa
フルテキストURL Sci_Rep_15_7_8239.pdf
著者 Vavrick, Christopher J.| Muto, Chiaki| Hasunuma, Tomohisa| Kimura, Yoshinobu| Araki, Michihiro| Wu, Yan| Gao, George F.| Ohrui, Hiroshi| Izumi, Minoru| Kiyota, Hiromasa|
抄録 The design, synthesis and application of N-acetylneuraminic acid-derived compounds bearing anomeric sulfo functional groups are described. These novel compounds, which we refer to as sulfo-sialic acid analogues, include 2-decarboxy-2-deoxy-2-sulfo-N-acetylneuraminic acid and its 4-deoxy-3,4-dehydrogenated pseudoglycal. While 2-decarboxy-2-deoxy-2-sulfo-N-acetylneuraminic acid contains no further modifications of the 2-deoxy-pyranose ring, it is still a more potent inhibitor of avian-origin H5N1 neuraminidase (NA) and drug-resistant His275Tyr NA as compared to the oxocarbenium ion transition state analogue 2,3-dehydro-2-deoxy-N-acetylneuraminic acid. The sulfo-sialic acid analogues described in this report are also more potent inhibitors of influenza NA (up to 40-fold) and bacterial NA (up to 8.5-fold) relative to the corresponding anomeric phosphonic acids. These results confirm that this novel anomeric sulfo modification offers great potential to improve the potency of next-generation NA inhibitors including covalent inhibitors.
備考 This is an article published by Science
発行日 2017-08
出版物タイトル Scientific Reports
7巻
1号
出版者 Nature Publishing Group
開始ページ 8239
ISSN 2045-2322
資料タイプ 学術雑誌論文
言語 English
OAI-PMH Set 岡山大学
著作権者 https://creativecommons.org/licenses/by-nc-nd/4.0/deed.ja
論文のバージョン publisher
PubMed ID 28811524
DOI 10.1038/s41598-017-07836-y
Web of Sience KeyUT 000407570000116
関連URL https://doi.org/10.1038/s41598-017-07836-y
フルテキストURL 17P-SO3-Sia-SR.pdf
著者 Vavricka, Christopher J.| Muto, Chiaki| Hasunuma, Tomohisa| Kimura, Yoshinobu| Araki, Michihiro| Wu, Yan| Gao, George F.| Ohrui, Hiroshi| Izumi, Minoru| Kiyota, Hiromasa|
抄録 The design, synthesis and application of N-acetylneuraminic acid-derived compounds bearing anomeric sulfo functional groups are described. These novel compounds, which we refer to as sulfo-sialic acid analogues, include 2-decarboxy-2-deoxy-2-sulfo-N-acetylneuraminic acid and its 4-deoxy-3,4-dehydrogenated pseudoglycal. While 2-decarboxy-2-deoxy-2-sulfo-N-acetylneuraminic acid contains no further modifications of the 2-deoxy-pyranose ring, it is still a more potent inhibitor of avian-origin H5N1 neuraminidase (NA) and drug-resistant His275Tyr NA as compared to the oxocarbenium ion transition state analogue 2,3-dehydro-2-deoxy-N-acetylneuraminic acid. The sulfo-sialic acid analogues described in this report are also more potent inhibitors of influenza NA (up to 40-fold) and bacterial NA (up to 8.5-fold) relative to the corresponding anomeric phosphonic acids. These results confirm that this novel anomeric sulfo modification offers great potential to improve the potency of next-generation NA inhibitors including covalent inhibitors.
キーワード Antiviral agents Drug discovery and development Glycosides
発行日 2017-08
出版物タイトル Scientific Reports
7巻
1号
出版者 Nature Publishing Group
開始ページ 8239
ISSN 2045-2322
資料タイプ 学術雑誌論文
言語 English
OAI-PMH Set 岡山大学
著作権者 https://creativecommons.org/licenses/by-nc-nd/4.0/deed.ja
論文のバージョン publisher
PubMed ID 28811524
DOI 10.1038/s41598-017-07836-y
Web of Sience KeyUT 000407570000116
関連URL https://doi.org/10.1038/s41598-017-07836-y
著者 清田 洋正|
発行日 2017-02-01
出版物タイトル 岡山大学農学部学術報告
106巻
資料タイプ 紀要論文
著者 Wu, Yi-Bing| Liu, Dan| Liu, Pei-Yu| Yang, Xue-Mei| Liao, Man| Lu, Nan-Nan| Sauriol, FranÅoise| Gu, Yu-Cheng| Shi, Qing-Wen| 清田 洋正| Dong, Mei|
発行日 2015-05-26
出版物タイトル Helvetica Chimica Acta
98巻
5号
資料タイプ 学術雑誌論文