Synthesis of phosphonate derivatives of uridine, cytidine, and cytosine arabinoside

Kang Yeoun Jung; Raymond J. Hohl; Andrew J. Wiemer; David F. Wiemer

doi:10.1016/S0968-0896(00)00183-8

Synthesis of phosphonate derivatives of uridine, cytidine, and cytosine arabinoside

Kang Yeoun Jung, Raymond J. Hohl, Andrew J. Wiemer, David F. Wiemer

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Abstract

The vinyl phosphonate derivatives of uridine, cytidine, and cytosine arabinoside (ara-C) have been prepared through oxidation of appropriately protected nucleosides to the 5' aldehydes and Wittig condensation with [(diethoxyphosphinyl)methylidine]triphenylphosphorane. Dihydroxylation of these vinyl phosphonates with an AD-mix reagent generated the new 5',6'-dihydroxy-6'-phosphonates. After hydrolysis of the phosphonate esters and the various protecting groups, the six phosphonic acids were tested for their ability to serve as substrates for the enzyme nucleotide monophosphate kinase and for their toxicity to K562 cells. Copyright (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	2501-2509
Number of pages	9
Journal	Bioorganic and Medicinal Chemistry
Volume	8
Issue number	10
DOIs	https://doi.org/10.1016/S0968-0896(00)00183-8
State	Published - Oct 2000

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/S0968-0896(00)00183-8

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title = "Synthesis of phosphonate derivatives of uridine, cytidine, and cytosine arabinoside",

abstract = "The vinyl phosphonate derivatives of uridine, cytidine, and cytosine arabinoside (ara-C) have been prepared through oxidation of appropriately protected nucleosides to the 5' aldehydes and Wittig condensation with [(diethoxyphosphinyl)methylidine]triphenylphosphorane. Dihydroxylation of these vinyl phosphonates with an AD-mix reagent generated the new 5',6'-dihydroxy-6'-phosphonates. After hydrolysis of the phosphonate esters and the various protecting groups, the six phosphonic acids were tested for their ability to serve as substrates for the enzyme nucleotide monophosphate kinase and for their toxicity to K562 cells. Copyright (C) 2000 Elsevier Science Ltd.",

author = "Jung, {Kang Yeoun} and Hohl, {Raymond J.} and Wiemer, {Andrew J.} and Wiemer, {David F.}",

note = "Funding Information: We thank Kangnung National University for the research leave which allowed Prof. Jung to participate in this investigation. Financial support from the Leukemia and Lymphoma Society (formerly known as the Leukemia Society of America) (LSA99-6059) is gratefully acknowledged. Copyright: Copyright 2007 Elsevier B.V., All rights reserved.",

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doi = "10.1016/S0968-0896(00)00183-8",

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AU - Jung, Kang Yeoun

AU - Hohl, Raymond J.

AU - Wiemer, Andrew J.

AU - Wiemer, David F.

N1 - Funding Information: We thank Kangnung National University for the research leave which allowed Prof. Jung to participate in this investigation. Financial support from the Leukemia and Lymphoma Society (formerly known as the Leukemia Society of America) (LSA99-6059) is gratefully acknowledged. Copyright: Copyright 2007 Elsevier B.V., All rights reserved.

PY - 2000/10

Y1 - 2000/10

N2 - The vinyl phosphonate derivatives of uridine, cytidine, and cytosine arabinoside (ara-C) have been prepared through oxidation of appropriately protected nucleosides to the 5' aldehydes and Wittig condensation with [(diethoxyphosphinyl)methylidine]triphenylphosphorane. Dihydroxylation of these vinyl phosphonates with an AD-mix reagent generated the new 5',6'-dihydroxy-6'-phosphonates. After hydrolysis of the phosphonate esters and the various protecting groups, the six phosphonic acids were tested for their ability to serve as substrates for the enzyme nucleotide monophosphate kinase and for their toxicity to K562 cells. Copyright (C) 2000 Elsevier Science Ltd.

AB - The vinyl phosphonate derivatives of uridine, cytidine, and cytosine arabinoside (ara-C) have been prepared through oxidation of appropriately protected nucleosides to the 5' aldehydes and Wittig condensation with [(diethoxyphosphinyl)methylidine]triphenylphosphorane. Dihydroxylation of these vinyl phosphonates with an AD-mix reagent generated the new 5',6'-dihydroxy-6'-phosphonates. After hydrolysis of the phosphonate esters and the various protecting groups, the six phosphonic acids were tested for their ability to serve as substrates for the enzyme nucleotide monophosphate kinase and for their toxicity to K562 cells. Copyright (C) 2000 Elsevier Science Ltd.

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Synthesis of phosphonate derivatives of uridine, cytidine, and cytosine arabinoside

Abstract

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