The Synthesis of 2'-Deoxyguanosines Having An Arylamino Group at the C-8 Position

Chin Yi Huang; Francis Johnson

doi:10.1080/10575639208048877

The Synthesis of 2'-Deoxyguanosines Having An Arylamino Group at the C-8 Position

Chin Yi Huang
, Francis Johnson

Pharmacological Sciences

Stony Brook University

Stony Brook University

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

3 Scopus citations

Abstract

A general route is described and the synthesis of 8-arylamino derivatives of 2'-deoxyguanosine. The method takes advantage of (a) the far greater stability of the ribonucleoside series to acid conditions during the introduction of the aminoaryl group and (b) a modified form of Barton's radical deoxygenation procedure to remove the 2'-hydroxyl group. The synthetic pathway allows the preparation of the desired materials on a gram scale and avoids the use of an ultimate carcinogen as an intermediate.

Original language	English
Pages (from-to)	3-7
Number of pages	5
Journal	Natural Product Letters
Volume	1
Issue number	1
DOIs	https://doi.org/10.1080/10575639208048877
State	Published - Jun 1992

Keywords

2-deoxy-8-(arylamino)guanosine
aminofluorene
carcinogenic amines
nitrenium ion
synthesis
ultimate carcinogens

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10.1080/10575639208048877

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abstract = "A general route is described and the synthesis of 8-arylamino derivatives of 2'-deoxyguanosine. The method takes advantage of (a) the far greater stability of the ribonucleoside series to acid conditions during the introduction of the aminoaryl group and (b) a modified form of Barton's radical deoxygenation procedure to remove the 2'-hydroxyl group. The synthetic pathway allows the preparation of the desired materials on a gram scale and avoids the use of an ultimate carcinogen as an intermediate.",

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AB - A general route is described and the synthesis of 8-arylamino derivatives of 2'-deoxyguanosine. The method takes advantage of (a) the far greater stability of the ribonucleoside series to acid conditions during the introduction of the aminoaryl group and (b) a modified form of Barton's radical deoxygenation procedure to remove the 2'-hydroxyl group. The synthetic pathway allows the preparation of the desired materials on a gram scale and avoids the use of an ultimate carcinogen as an intermediate.

KW - 2-deoxy-8-(arylamino)guanosine

KW - aminofluorene

KW - carcinogenic amines

KW - nitrenium ion

KW - synthesis

KW - ultimate carcinogens

UR - https://www.scopus.com/pages/publications/0043222596

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ER -

The Synthesis of 2'-Deoxyguanosines Having An Arylamino Group at the C-8 Position

Abstract

Keywords

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