Truncated fluorocyclopentenyl pyrimidines as S-adenosylhomocysteine hydrolase inhibitors

Yeon Hee Park; Won Jun Choi; Amol S. Tipnis; Kang Man Lee; Lak Shin Jeong

doi:10.1080/15257770903054316

Truncated fluorocyclopentenyl pyrimidines as S-adenosylhomocysteine hydrolase inhibitors

Yeon Hee Park
, Won Jun Choi
, Amol S. Tipnis
, Kang Man Lee
, Lak Shin Jeong

Department of Pharmacy

Ewha Womans University

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

6 Scopus citations

Abstract

On the basis of inhibitory activity of truncated cyclopentenyl cytosine against S-adenosylhomocysteine hydrolase (SAH), its fluorocyclopentenyl pyrimidine derivatives were efficiently synthesized from D-ribose via electrophilic fluorination as a key step. The final nucleosides were evaluated for SAH inhibitory activity, among which the uracil derivative 9 showed significant inhibitory activity (IC50 = 8.53 M). They were also evaluated for cytotoxic effects in several human cancer cell lines such as fibro sarcoma, stomach cancer, leukemia, and colon cancer, but they did not show any cytotoxic effects up to 100 M, indicating that 4'-hydroxymethyl groups are essential for the anticancer activity.

Original language	English
Pages (from-to)	601-613
Number of pages	13
Journal	Nucleosides, Nucleotides and Nucleic Acids
Volume	28
Issue number	5-7
DOIs	https://doi.org/10.1080/15257770903054316
State	Published - May 2009

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

Electrophilic fluorination
S-adenosylhomocysteine hydrolase
Truncated nucleosides

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10.1080/15257770903054316

Cite this

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title = "Truncated fluorocyclopentenyl pyrimidines as S-adenosylhomocysteine hydrolase inhibitors",

abstract = "On the basis of inhibitory activity of truncated cyclopentenyl cytosine against S-adenosylhomocysteine hydrolase (SAH), its fluorocyclopentenyl pyrimidine derivatives were efficiently synthesized from D-ribose via electrophilic fluorination as a key step. The final nucleosides were evaluated for SAH inhibitory activity, among which the uracil derivative 9 showed significant inhibitory activity (IC50 = 8.53 M). They were also evaluated for cytotoxic effects in several human cancer cell lines such as fibro sarcoma, stomach cancer, leukemia, and colon cancer, but they did not show any cytotoxic effects up to 100 M, indicating that 4'-hydroxymethyl groups are essential for the anticancer activity.",

keywords = "Electrophilic fluorination, S-adenosylhomocysteine hydrolase, Truncated nucleosides",

author = "Park, \{Yeon Hee\} and Choi, \{Won Jun\} and Tipnis, \{Amol S.\} and Lee, \{Kang Man\} and Jeong, \{Lak Shin\}",

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doi = "10.1080/15257770903054316",

language = "English",

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T1 - Truncated fluorocyclopentenyl pyrimidines as S-adenosylhomocysteine hydrolase inhibitors

AU - Park, Yeon Hee

AU - Choi, Won Jun

AU - Tipnis, Amol S.

AU - Lee, Kang Man

AU - Jeong, Lak Shin

PY - 2009/5

Y1 - 2009/5

N2 - On the basis of inhibitory activity of truncated cyclopentenyl cytosine against S-adenosylhomocysteine hydrolase (SAH), its fluorocyclopentenyl pyrimidine derivatives were efficiently synthesized from D-ribose via electrophilic fluorination as a key step. The final nucleosides were evaluated for SAH inhibitory activity, among which the uracil derivative 9 showed significant inhibitory activity (IC50 = 8.53 M). They were also evaluated for cytotoxic effects in several human cancer cell lines such as fibro sarcoma, stomach cancer, leukemia, and colon cancer, but they did not show any cytotoxic effects up to 100 M, indicating that 4'-hydroxymethyl groups are essential for the anticancer activity.

AB - On the basis of inhibitory activity of truncated cyclopentenyl cytosine against S-adenosylhomocysteine hydrolase (SAH), its fluorocyclopentenyl pyrimidine derivatives were efficiently synthesized from D-ribose via electrophilic fluorination as a key step. The final nucleosides were evaluated for SAH inhibitory activity, among which the uracil derivative 9 showed significant inhibitory activity (IC50 = 8.53 M). They were also evaluated for cytotoxic effects in several human cancer cell lines such as fibro sarcoma, stomach cancer, leukemia, and colon cancer, but they did not show any cytotoxic effects up to 100 M, indicating that 4'-hydroxymethyl groups are essential for the anticancer activity.

KW - Electrophilic fluorination

KW - S-adenosylhomocysteine hydrolase

KW - Truncated nucleosides

UR - https://www.scopus.com/pages/publications/75749089989

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DO - 10.1080/15257770903054316

M3 - Article

C2 - 20183604

AN - SCOPUS:75749089989

SN - 1525-7770

VL - 28

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EP - 613

JO - Nucleosides, Nucleotides and Nucleic Acids

JF - Nucleosides, Nucleotides and Nucleic Acids

IS - 5-7

ER -

Truncated fluorocyclopentenyl pyrimidines as S-adenosylhomocysteine hydrolase inhibitors

Abstract

UN SDGs

Keywords

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