Concise synthesis of 5,6-dihydrovaltrate leading to enhanced Rev-export inhibitory congener

Satoru Tamura; Katsuaki Fujiwara; Nobuhiro Shimizu; Shingo Todo; Nobutoshi Murakami

doi:10.1016/j.bmc.2010.06.079

Concise synthesis of 5,6-dihydrovaltrate leading to enhanced Rev-export inhibitory congener

Satoru Tamura, Katsuaki Fujiwara, Nobuhiro Shimizu, Shingo Todo, Nobutoshi Murakami

理学研究科・化学専攻

研究成果: Article › 査読

13 被引用数 (Scopus)

抄録

The concise synthesis of 5,6-dihydrovaltrate (2), the bioisostere of valtrate (1) showing anti-HIV activity by inhibition for nuclear export of Rev, has been achieved from the commercially available iridoid genipin (3). Analysis of steric influence of the substituents linked to the three hydroxyl groups was conducted by the synthesized three analogs (2a-2c). Consequently, attenuation of steric hindrance around the epoxy portion was revealed to enhance inhibitory potency for Rev-export. In addition to this finding, 1-acetoxy analog 2b was disclosed as the promising Rev-export inhibitor superior to 1.

本文言語	English
ページ（範囲）	5975-5980
ページ数	6
ジャーナル	Bioorganic and Medicinal Chemistry
巻	18
号	16
DOI	https://doi.org/10.1016/j.bmc.2010.06.079
出版ステータス	Published - 2010 8月 15

ASJC Scopus subject areas

生化学
分子医療
分子生物学
薬科学
創薬
臨床生化学
有機化学

UN SDG

この成果は、次の持続可能な開発目標に貢献しています

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title = "Concise synthesis of 5,6-dihydrovaltrate leading to enhanced Rev-export inhibitory congener",

abstract = "The concise synthesis of 5,6-dihydrovaltrate (2), the bioisostere of valtrate (1) showing anti-HIV activity by inhibition for nuclear export of Rev, has been achieved from the commercially available iridoid genipin (3). Analysis of steric influence of the substituents linked to the three hydroxyl groups was conducted by the synthesized three analogs (2a-2c). Consequently, attenuation of steric hindrance around the epoxy portion was revealed to enhance inhibitory potency for Rev-export. In addition to this finding, 1-acetoxy analog 2b was disclosed as the promising Rev-export inhibitor superior to 1.",

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AU - Tamura, Satoru

AU - Fujiwara, Katsuaki

AU - Shimizu, Nobuhiro

AU - Todo, Shingo

AU - Murakami, Nobutoshi

PY - 2010/8/15

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N2 - The concise synthesis of 5,6-dihydrovaltrate (2), the bioisostere of valtrate (1) showing anti-HIV activity by inhibition for nuclear export of Rev, has been achieved from the commercially available iridoid genipin (3). Analysis of steric influence of the substituents linked to the three hydroxyl groups was conducted by the synthesized three analogs (2a-2c). Consequently, attenuation of steric hindrance around the epoxy portion was revealed to enhance inhibitory potency for Rev-export. In addition to this finding, 1-acetoxy analog 2b was disclosed as the promising Rev-export inhibitor superior to 1.

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KW - 5,6-Dihydrovaltrate

KW - Anti-HIV

KW - Genipin

KW - Iridoid

KW - Rev-export inhibitor

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Concise synthesis of 5,6-dihydrovaltrate leading to enhanced Rev-export inhibitory congener

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ASJC Scopus subject areas

UN SDG

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