Synthesis and anti-HIV activity of L-2'-fluoro-2',3'-unsaturated purine nucleosides

Yongseok Choi; Kyeong Lee; Joon H. Hong; Raymond F. Schinazi; Chung K. Chu

doi:10.1016/S0040-4039(98)00841-7

Synthesis and anti-HIV activity of L-2'-fluoro-2',3'-unsaturated purine nucleosides

Yongseok Choi
, Kyeong Lee
, Joon H. Hong
, Raymond F. Schinazi
, Chung K. Chu

Department of Pharmacy

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

26 Scopus citations

Abstract

The synthesis of 9-(2,3-dideoxy-2-fluoro-L-glycero-pent-2-eno- furanosyl)adenine and-hypoxanthine has been accomplished by direct condensation of silylated 6-chloropurine with key intermediates 8, which were prepared starting from 2,3-0-isopropylidene-L-glyceraldehyde. The synthesized nucleosides were evaluated against HIV-1 in vitro in primary human lymphocytes (PMB cells). It was found that β-L-Fd4A 12 exhibited moderately potent anti-HIV activity (EC₅₀ 1.5 μM).

Original language	English
Pages (from-to)	4437-4440
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	25
DOIs	https://doi.org/10.1016/S0040-4039(98)00841-7
State	Published - 18 Jun 1998

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10.1016/S0040-4039(98)00841-7

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title = "Synthesis and anti-HIV activity of L-2'-fluoro-2',3'-unsaturated purine nucleosides",

abstract = "The synthesis of 9-(2,3-dideoxy-2-fluoro-L-glycero-pent-2-eno- furanosyl)adenine and-hypoxanthine has been accomplished by direct condensation of silylated 6-chloropurine with key intermediates 8, which were prepared starting from 2,3-0-isopropylidene-L-glyceraldehyde. The synthesized nucleosides were evaluated against HIV-1 in vitro in primary human lymphocytes (PMB cells). It was found that β-L-Fd4A 12 exhibited moderately potent anti-HIV activity (EC50 1.5 μM).",

author = "Yongseok Choi and Kyeong Lee and Hong, \{Joon H.\} and Schinazi, \{Raymond F.\} and Chu, \{Chung K.\}",

year = "1998",

month = jun,

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doi = "10.1016/S0040-4039(98)00841-7",

language = "English",

volume = "39",

pages = "4437--4440",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis and anti-HIV activity of L-2'-fluoro-2',3'-unsaturated purine nucleosides

AU - Choi, Yongseok

AU - Lee, Kyeong

AU - Hong, Joon H.

AU - Schinazi, Raymond F.

AU - Chu, Chung K.

PY - 1998/6/18

Y1 - 1998/6/18

N2 - The synthesis of 9-(2,3-dideoxy-2-fluoro-L-glycero-pent-2-eno- furanosyl)adenine and-hypoxanthine has been accomplished by direct condensation of silylated 6-chloropurine with key intermediates 8, which were prepared starting from 2,3-0-isopropylidene-L-glyceraldehyde. The synthesized nucleosides were evaluated against HIV-1 in vitro in primary human lymphocytes (PMB cells). It was found that β-L-Fd4A 12 exhibited moderately potent anti-HIV activity (EC50 1.5 μM).

AB - The synthesis of 9-(2,3-dideoxy-2-fluoro-L-glycero-pent-2-eno- furanosyl)adenine and-hypoxanthine has been accomplished by direct condensation of silylated 6-chloropurine with key intermediates 8, which were prepared starting from 2,3-0-isopropylidene-L-glyceraldehyde. The synthesized nucleosides were evaluated against HIV-1 in vitro in primary human lymphocytes (PMB cells). It was found that β-L-Fd4A 12 exhibited moderately potent anti-HIV activity (EC50 1.5 μM).

UR - https://www.scopus.com/pages/publications/0032543455

U2 - 10.1016/S0040-4039(98)00841-7

DO - 10.1016/S0040-4039(98)00841-7

M3 - Article

AN - SCOPUS:0032543455

SN - 0040-4039

VL - 39

SP - 4437

EP - 4440

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 25

ER -

Synthesis and anti-HIV activity of L-2'-fluoro-2',3'-unsaturated purine nucleosides

Abstract

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