Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents

Lak Shin Jeong; Yoo Na Choi; Dilip K. Tosh; Won Jun Choi; Hea Ok Kim; Jungwon Choi

doi:10.1016/j.bmc.2008.10.034

Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents

Lak Shin Jeong
, Yoo Na Choi
, Dilip K. Tosh
, Won Jun Choi
, Hea Ok Kim
, Jungwon Choi

Department of Pharmacy

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

32 Scopus citations

Abstract

On the basis of potent anti-HIV activity of 2',3'-dideoxynucleosides (ddNs), their bioisosteric analogues, 2',3'-dideoxy-4'-selenonucleosides (4'-seleno-ddNs) were first synthesized from a chiral template, d-glutamic acid using stereoselective ring-closure reaction of the dimesylate with Se^2- and Pummerer type condensation of the selenoxide with nucleobases as key steps. X-ray crystallographic analysis indicated that 4'-seleno-ddNs adopted the same C2'-endo/C3'-exo (South) conformation as anti-HIV active ddNs, but did not show anti-HIV activity, indicating that RT seems to prefer the C2'-exo/C3'-endo (North) conformation on binding with their triphosphates.

Original language	English
Pages (from-to)	9891-9897
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	16
Issue number	23
DOIs	https://doi.org/10.1016/j.bmc.2008.10.034
State	Published - 1 Dec 2008

Keywords

2′,3′-Dideoxy-4′-selenonucleosides
2′,3′-Dideoxycytidine
Anti-HIV agents
Pummerer type condensation
South conformation

UN SDGs

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

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10.1016/j.bmc.2008.10.034

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title = "Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents",

abstract = "On the basis of potent anti-HIV activity of 2',3'-dideoxynucleosides (ddNs), their bioisosteric analogues, 2',3'-dideoxy-4'-selenonucleosides (4'-seleno-ddNs) were first synthesized from a chiral template, d-glutamic acid using stereoselective ring-closure reaction of the dimesylate with Se2- and Pummerer type condensation of the selenoxide with nucleobases as key steps. X-ray crystallographic analysis indicated that 4'-seleno-ddNs adopted the same C2'-endo/C3'-exo (South) conformation as anti-HIV active ddNs, but did not show anti-HIV activity, indicating that RT seems to prefer the C2'-exo/C3'-endo (North) conformation on binding with their triphosphates.",

keywords = "2′,3′-Dideoxy-4′-selenonucleosides, 2′,3′-Dideoxycytidine, Anti-HIV agents, Pummerer type condensation, South conformation",

author = "Jeong, \{Lak Shin\} and Choi, \{Yoo Na\} and Tosh, \{Dilip K.\} and Choi, \{Won Jun\} and Kim, \{Hea Ok\} and Jungwon Choi",

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doi = "10.1016/j.bmc.2008.10.034",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry",

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T1 - Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents

AU - Jeong, Lak Shin

AU - Choi, Yoo Na

AU - Tosh, Dilip K.

AU - Choi, Won Jun

AU - Kim, Hea Ok

AU - Choi, Jungwon

PY - 2008/12/1

Y1 - 2008/12/1

N2 - On the basis of potent anti-HIV activity of 2',3'-dideoxynucleosides (ddNs), their bioisosteric analogues, 2',3'-dideoxy-4'-selenonucleosides (4'-seleno-ddNs) were first synthesized from a chiral template, d-glutamic acid using stereoselective ring-closure reaction of the dimesylate with Se2- and Pummerer type condensation of the selenoxide with nucleobases as key steps. X-ray crystallographic analysis indicated that 4'-seleno-ddNs adopted the same C2'-endo/C3'-exo (South) conformation as anti-HIV active ddNs, but did not show anti-HIV activity, indicating that RT seems to prefer the C2'-exo/C3'-endo (North) conformation on binding with their triphosphates.

AB - On the basis of potent anti-HIV activity of 2',3'-dideoxynucleosides (ddNs), their bioisosteric analogues, 2',3'-dideoxy-4'-selenonucleosides (4'-seleno-ddNs) were first synthesized from a chiral template, d-glutamic acid using stereoselective ring-closure reaction of the dimesylate with Se2- and Pummerer type condensation of the selenoxide with nucleobases as key steps. X-ray crystallographic analysis indicated that 4'-seleno-ddNs adopted the same C2'-endo/C3'-exo (South) conformation as anti-HIV active ddNs, but did not show anti-HIV activity, indicating that RT seems to prefer the C2'-exo/C3'-endo (North) conformation on binding with their triphosphates.

KW - 2′,3′-Dideoxy-4′-selenonucleosides

KW - 2′,3′-Dideoxycytidine

KW - Anti-HIV agents

KW - Pummerer type condensation

KW - South conformation

UR - https://www.scopus.com/pages/publications/55749104380

U2 - 10.1016/j.bmc.2008.10.034

DO - 10.1016/j.bmc.2008.10.034

M3 - Article

C2 - 18977147

AN - SCOPUS:55749104380

SN - 0968-0896

VL - 16

SP - 9891

EP - 9897

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 23

ER -

Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents

Abstract

Keywords

UN SDGs

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