Synthesis of 5-halogeno-6-amino-2'-deoxyuridines and their analogs as potential inhibitors of thymidine phosphorylase

Bai Chuan Pan; Zhi Hao Chen; Edward Chu; Ming Yu WangChu; Shih Hsi Chu

doi:10.1080/07328319808004324

Synthesis of 5-halogeno-6-amino-2'-deoxyuridines and their analogs as potential inhibitors of thymidine phosphorylase

Bai Chuan Pan, Zhi Hao Chen, Edward Chu, Ming Yu WangChu, Shih Hsi Chu

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11 Scopus citations

Abstract

5-Halogeno-6-amino-2'-deoxyuridines were synthesized from 2'- deoxyuridine as potential thymidine phosphorylase (ThdPase) inhibitors. Among the compounds synthesized, 5-bromo-6-amino-2'-deoxyuridine (6) and 5-iodo-6- amino-2'-deoxyuridine (9) were found to inhibit ThdPase activity with IC50 values of 1.3 μM and 6.5 μM, respectively. In vitro cell culture studies showed that compound (6) can significantly enhance the cytotoxic effects of 5-fluoro-2'-deoxyuridine against a human colon cancer HCT-8 cell line.

Original language	English (US)
Pages (from-to)	2367-2382
Number of pages	16
Journal	Nucleosides and Nucleotides
Volume	17
Issue number	12
DOIs	https://doi.org/10.1080/07328319808004324
State	Published - 1998
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Genetics

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

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10.1080/07328319808004324

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@article{e1003cbd8d0248fda6668a0519d00dc4,

title = "Synthesis of 5-halogeno-6-amino-2'-deoxyuridines and their analogs as potential inhibitors of thymidine phosphorylase",

abstract = "5-Halogeno-6-amino-2'-deoxyuridines were synthesized from 2'- deoxyuridine as potential thymidine phosphorylase (ThdPase) inhibitors. Among the compounds synthesized, 5-bromo-6-amino-2'-deoxyuridine (6) and 5-iodo-6- amino-2'-deoxyuridine (9) were found to inhibit ThdPase activity with IC50 values of 1.3 μM and 6.5 μM, respectively. In vitro cell culture studies showed that compound (6) can significantly enhance the cytotoxic effects of 5-fluoro-2'-deoxyuridine against a human colon cancer HCT-8 cell line.",

author = "Pan, {Bai Chuan} and Chen, {Zhi Hao} and Edward Chu and WangChu, {Ming Yu} and Chu, {Shih Hsi}",

note = "Funding Information: Acknowledgment: This work was supported by Taiho Pharmaceutical Co., Ltd. and USPHS grant CA 39427 (to S.H.Chu.). We would like to thank Dr. James Van Epp of the Department of Chemistry, Brown University for his assistance with the NMR spectra, and Dr. John Schmitz for assistance in the preparation of the manuscript.",

year = "1998",

doi = "10.1080/07328319808004324",

language = "English (US)",

volume = "17",

pages = "2367--2382",

journal = "Nucleosides and Nucleotides",

issn = "0732-8311",

publisher = "Taylor and Francis Ltd.",

number = "12",

}

TY - JOUR

T1 - Synthesis of 5-halogeno-6-amino-2'-deoxyuridines and their analogs as potential inhibitors of thymidine phosphorylase

AU - Pan, Bai Chuan

AU - Chen, Zhi Hao

AU - Chu, Edward

AU - WangChu, Ming Yu

AU - Chu, Shih Hsi

N1 - Funding Information: Acknowledgment: This work was supported by Taiho Pharmaceutical Co., Ltd. and USPHS grant CA 39427 (to S.H.Chu.). We would like to thank Dr. James Van Epp of the Department of Chemistry, Brown University for his assistance with the NMR spectra, and Dr. John Schmitz for assistance in the preparation of the manuscript.

PY - 1998

Y1 - 1998

N2 - 5-Halogeno-6-amino-2'-deoxyuridines were synthesized from 2'- deoxyuridine as potential thymidine phosphorylase (ThdPase) inhibitors. Among the compounds synthesized, 5-bromo-6-amino-2'-deoxyuridine (6) and 5-iodo-6- amino-2'-deoxyuridine (9) were found to inhibit ThdPase activity with IC50 values of 1.3 μM and 6.5 μM, respectively. In vitro cell culture studies showed that compound (6) can significantly enhance the cytotoxic effects of 5-fluoro-2'-deoxyuridine against a human colon cancer HCT-8 cell line.

AB - 5-Halogeno-6-amino-2'-deoxyuridines were synthesized from 2'- deoxyuridine as potential thymidine phosphorylase (ThdPase) inhibitors. Among the compounds synthesized, 5-bromo-6-amino-2'-deoxyuridine (6) and 5-iodo-6- amino-2'-deoxyuridine (9) were found to inhibit ThdPase activity with IC50 values of 1.3 μM and 6.5 μM, respectively. In vitro cell culture studies showed that compound (6) can significantly enhance the cytotoxic effects of 5-fluoro-2'-deoxyuridine against a human colon cancer HCT-8 cell line.

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DO - 10.1080/07328319808004324

M3 - Article

AN - SCOPUS:0031758864

SN - 0732-8311

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SP - 2367

EP - 2382

JO - Nucleosides and Nucleotides

JF - Nucleosides and Nucleotides

IS - 12

ER -

Synthesis of 5-halogeno-6-amino-2'-deoxyuridines and their analogs as potential inhibitors of thymidine phosphorylase

Abstract

ASJC Scopus subject areas

UN SDGs

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