Synthesis of (1R, 4S, 5R)-9-(4,5-bishydroxy-methylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] and selective inhibition of human immunodeficiency virus

Nobuya Katagiri; Akemi Toyota; Takuya Shiraishi; Hiroshi Sato; Chikara Kaneko

doi:10.1016/S0040-4039(00)92675-3

Synthesis of (1R, 4S, 5R)-9-(4,5-bishydroxy-methylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] and selective inhibition of human immunodeficiency virus

Nobuya Katagiri, Akemi Toyota, Takuya Shiraishi, Hiroshi Sato, Chikara Kaneko

PHA - Pharmacy

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

23 Citations (Scopus)

Abstract

(1R,4S,5R)-9(4,5-Bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] has been synthesized from (-)-Corey lactone in 11 steps and shown to have potent and selective effects against human immmunodeficiency virus type 1. The result demonstrated that the potent-HIV activity of racemic BCA obtained in our previous work is expressed solely by the (1R,4S,5R)-(-)-isomer.

Original language	English
Pages (from-to)	3507-3510
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	24
DOIs	https://doi.org/10.1016/S0040-4039(00)92675-3
Publication status	Published - 1992 Jun 9

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Synthesis of (1R, 4S, 5R)-9-(4,5-bishydroxy-methylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] and selective inhibition of human immunodeficiency virus. / Katagiri, Nobuya; Toyota, Akemi; Shiraishi, Takuya; Sato, Hiroshi; Kaneko, Chikara.

In: Tetrahedron Letters, Vol. 33, No. 24, 09.06.1992, p. 3507-3510.

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

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title = "Synthesis of (1R, 4S, 5R)-9-(4,5-bishydroxy-methylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] and selective inhibition of human immunodeficiency virus",

abstract = "(1R,4S,5R)-9(4,5-Bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] has been synthesized from (-)-Corey lactone in 11 steps and shown to have potent and selective effects against human immmunodeficiency virus type 1. The result demonstrated that the potent-HIV activity of racemic BCA obtained in our previous work is expressed solely by the (1R,4S,5R)-(-)-isomer.",

author = "Nobuya Katagiri and Akemi Toyota and Takuya Shiraishi and Hiroshi Sato and Chikara Kaneko",

note = "Funding Information: Acknowledgment. This work was supported in part by a Grant-in-Aid for Scientific Research on Priority Areas No. 03242104 from the Ministry of Education, Science and Culture, Japan. We are also grateful to Dr. Shinji Terao (Takeda Chemical Industries, Ltd.) for generous supply of samples of (-)-Corey lactone (monobenzoate, 1).",

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AU - Katagiri, Nobuya

AU - Toyota, Akemi

AU - Shiraishi, Takuya

AU - Sato, Hiroshi

AU - Kaneko, Chikara

N1 - Funding Information: Acknowledgment. This work was supported in part by a Grant-in-Aid for Scientific Research on Priority Areas No. 03242104 from the Ministry of Education, Science and Culture, Japan. We are also grateful to Dr. Shinji Terao (Takeda Chemical Industries, Ltd.) for generous supply of samples of (-)-Corey lactone (monobenzoate, 1).

PY - 1992/6/9

Y1 - 1992/6/9

N2 - (1R,4S,5R)-9(4,5-Bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] has been synthesized from (-)-Corey lactone in 11 steps and shown to have potent and selective effects against human immmunodeficiency virus type 1. The result demonstrated that the potent-HIV activity of racemic BCA obtained in our previous work is expressed solely by the (1R,4S,5R)-(-)-isomer.

AB - (1R,4S,5R)-9(4,5-Bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] has been synthesized from (-)-Corey lactone in 11 steps and shown to have potent and selective effects against human immmunodeficiency virus type 1. The result demonstrated that the potent-HIV activity of racemic BCA obtained in our previous work is expressed solely by the (1R,4S,5R)-(-)-isomer.

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Synthesis of (1R, 4S, 5R)-9-(4,5-bishydroxy-methylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] and selective inhibition of human immunodeficiency virus

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