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

20 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

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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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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.

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KW - Bioisostere

KW - Iridoid

KW - Rev-export inhibitor

KW - Valtrate

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