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

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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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",

year = "1992",

month = jun,

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doi = "10.1016/S0040-4039(00)92675-3",

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T1 - Synthesis of (1R, 4S, 5R)-9-(4,5-bishydroxy-methylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] and selective inhibition of human immunodeficiency virus

AU - Katagiri, Nobuya

AU - Toyota, Akemi

AU - Shiraishi, Takuya

AU - Sato, Hiroshi

AU - Kaneko, Chikara

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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