Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev

Satoru Tamura; Nobuhiro Shimizu; Katsuaki Fujiwara; Masafumi Kaneko; Tominori Kimura; Nobutoshi Murakami

doi:10.1016/j.bmcl.2010.02.038

Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev

Satoru Tamura, Nobuhiro Shimizu, Katsuaki Fujiwara, Masafumi Kaneko, Tominori Kimura, Nobutoshi Murakami

SCI - Chemistry

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

24 Citations (Scopus)

Abstract

Rational design by the MO calculation disclosed 5,6-dihydrovaltrate (2) as the bioisostere of valtrate (1), the Rev-export inhibitor with anti-HIV activity. The synthesis of 2 was accomplished by ingenious use of asymmetric Diels-Alder reaction and stereoselective epoxidation associated with the adjacent hydroxyl group. Because of similar biological potency to 1, the analog 2 should be recognized as a promising scaffold for new anti-HIV agents with an unprecedented mechanism of action, inhibition for nuclear export of Rev protein, in the conventional remedy.

Original language	English
Pages (from-to)	2159-2162
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	7
DOIs	https://doi.org/10.1016/j.bmcl.2010.02.038
Publication status	Published - 2010 Apr 1

Keywords

Anti-HIV
Bioisostere
Iridoid
Rev-export inhibitor
Valtrate

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmcl.2010.02.038

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title = "Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev",

abstract = "Rational design by the MO calculation disclosed 5,6-dihydrovaltrate (2) as the bioisostere of valtrate (1), the Rev-export inhibitor with anti-HIV activity. The synthesis of 2 was accomplished by ingenious use of asymmetric Diels-Alder reaction and stereoselective epoxidation associated with the adjacent hydroxyl group. Because of similar biological potency to 1, the analog 2 should be recognized as a promising scaffold for new anti-HIV agents with an unprecedented mechanism of action, inhibition for nuclear export of Rev protein, in the conventional remedy.",

keywords = "Anti-HIV, Bioisostere, Iridoid, Rev-export inhibitor, Valtrate",

author = "Satoru Tamura and Nobuhiro Shimizu and Katsuaki Fujiwara and Masafumi Kaneko and Tominori Kimura and Nobutoshi Murakami",

note = "Funding Information: This work was supported in part by Grants-in-Aid for Scientific Research (Grant No. 19590100 ) from the Ministry of Education, Science, Culture and Sports. The authors are grateful to the Shorai Foundation for Science and Technology financial support.",

year = "2010",

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doi = "10.1016/j.bmcl.2010.02.038",

language = "English",

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pages = "2159--2162",

journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev

AU - Tamura, Satoru

AU - Shimizu, Nobuhiro

AU - Fujiwara, Katsuaki

AU - Kaneko, Masafumi

AU - Kimura, Tominori

AU - Murakami, Nobutoshi

N1 - Funding Information: This work was supported in part by Grants-in-Aid for Scientific Research (Grant No. 19590100 ) from the Ministry of Education, Science, Culture and Sports. The authors are grateful to the Shorai Foundation for Science and Technology financial support.

PY - 2010/4/1

Y1 - 2010/4/1

N2 - Rational design by the MO calculation disclosed 5,6-dihydrovaltrate (2) as the bioisostere of valtrate (1), the Rev-export inhibitor with anti-HIV activity. The synthesis of 2 was accomplished by ingenious use of asymmetric Diels-Alder reaction and stereoselective epoxidation associated with the adjacent hydroxyl group. Because of similar biological potency to 1, the analog 2 should be recognized as a promising scaffold for new anti-HIV agents with an unprecedented mechanism of action, inhibition for nuclear export of Rev protein, in the conventional remedy.

AB - Rational design by the MO calculation disclosed 5,6-dihydrovaltrate (2) as the bioisostere of valtrate (1), the Rev-export inhibitor with anti-HIV activity. The synthesis of 2 was accomplished by ingenious use of asymmetric Diels-Alder reaction and stereoselective epoxidation associated with the adjacent hydroxyl group. Because of similar biological potency to 1, the analog 2 should be recognized as a promising scaffold for new anti-HIV agents with an unprecedented mechanism of action, inhibition for nuclear export of Rev protein, in the conventional remedy.

KW - Anti-HIV

KW - Bioisostere

KW - Iridoid

KW - Rev-export inhibitor

KW - Valtrate

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DO - 10.1016/j.bmcl.2010.02.038

M3 - Article

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EP - 2162

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

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ER -

Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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