Synthesis of pyrrolo[2,3-d]pyrimidine derivatives and their antiproliferative activity against melanoma cell line

Myung Ho Jung; Hwan Kim; Won Kyoung Choi; Mohammed I. El-Gamal; Jin Hun Park; Kyung Ho Yoo; Tae Bo Sim; So Ha Lee; Daejin Baek; Jung Mi Hah; Jung Hyuck Cho; Chang Hyun Oh

doi:10.1016/j.bmcl.2009.10.051

Synthesis of pyrrolo[2,3-d]pyrimidine derivatives and their antiproliferative activity against melanoma cell line

Myung Ho Jung, Hwan Kim, Won Kyoung Choi, Mohammed I. El-Gamal, Jin Hun Park, Kyung Ho Yoo, Tae Bo Sim, So Ha Lee, Daejin Baek, Jung Mi Hah, Jung Hyuck Cho, Chang Hyun Oh

KU-KIST Graduate School of Converging Science and Technology

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

50 Citations (Scopus)

Abstract

Synthesis of a new series of diarylureas and amides having pyrrolo[2,3-d]pyrimidine scaffold is described. Their in vitro antiproliferative activities against A375 human melanoma cell line and HS 27 fibroblast cell line were tested and the effect of substituents on pyrrolo[2,3-d]pyrimidine was investigated. The newly synthesized compounds, except N-acetyl derivatives (Id, Ie, and Im), generally showed superior or similar activity against A375 to Sorafenib. Among all of these derivatives, compounds Iq and Ir having imidazole and morpholine moieties, respectively, showed the most potent antiproliferative activity against A375.

Original language	English
Pages (from-to)	6538-6543
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	23
DOIs	https://doi.org/10.1016/j.bmcl.2009.10.051
Publication status	Published - 2009 Dec 1

Bibliographical note

Funding Information:
We are grateful to the Korea Institute of Science and Technology (KIST) for financial support.

Keywords

A375
Antiproliferative activity
HS 27
Melanoma
Pyrrolo[2,3-d]pyrimidine

ASJC Scopus subject areas

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

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10.1016/j.bmcl.2009.10.051

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Jung, M. H., Kim, H., Choi, W. K., El-Gamal, M. I., Park, J. H., Yoo, K. H., Sim, T. B., Lee, S. H., Baek, D., Hah, J. M., Cho, J. H., & Oh, C. H. (2009). Synthesis of pyrrolo[2,3-d]pyrimidine derivatives and their antiproliferative activity against melanoma cell line. Bioorganic and Medicinal Chemistry Letters, 19(23), 6538-6543. https://doi.org/10.1016/j.bmcl.2009.10.051

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title = "Synthesis of pyrrolo[2,3-d]pyrimidine derivatives and their antiproliferative activity against melanoma cell line",

abstract = "Synthesis of a new series of diarylureas and amides having pyrrolo[2,3-d]pyrimidine scaffold is described. Their in vitro antiproliferative activities against A375 human melanoma cell line and HS 27 fibroblast cell line were tested and the effect of substituents on pyrrolo[2,3-d]pyrimidine was investigated. The newly synthesized compounds, except N-acetyl derivatives (Id, Ie, and Im), generally showed superior or similar activity against A375 to Sorafenib. Among all of these derivatives, compounds Iq and Ir having imidazole and morpholine moieties, respectively, showed the most potent antiproliferative activity against A375.",

keywords = "A375, Antiproliferative activity, HS 27, Melanoma, Pyrrolo[2,3-d]pyrimidine",

author = "Jung, {Myung Ho} and Hwan Kim and Choi, {Won Kyoung} and El-Gamal, {Mohammed I.} and Park, {Jin Hun} and Yoo, {Kyung Ho} and Sim, {Tae Bo} and Lee, {So Ha} and Daejin Baek and Hah, {Jung Mi} and Cho, {Jung Hyuck} and Oh, {Chang Hyun}",

note = "Funding Information: We are grateful to the Korea Institute of Science and Technology (KIST) for financial support.",

year = "2009",

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doi = "10.1016/j.bmcl.2009.10.051",

language = "English",

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AU - Jung, Myung Ho

AU - Kim, Hwan

AU - Choi, Won Kyoung

AU - El-Gamal, Mohammed I.

AU - Park, Jin Hun

AU - Yoo, Kyung Ho

AU - Sim, Tae Bo

AU - Lee, So Ha

AU - Baek, Daejin

AU - Hah, Jung Mi

AU - Cho, Jung Hyuck

AU - Oh, Chang Hyun

N1 - Funding Information: We are grateful to the Korea Institute of Science and Technology (KIST) for financial support.

PY - 2009/12/1

Y1 - 2009/12/1

N2 - Synthesis of a new series of diarylureas and amides having pyrrolo[2,3-d]pyrimidine scaffold is described. Their in vitro antiproliferative activities against A375 human melanoma cell line and HS 27 fibroblast cell line were tested and the effect of substituents on pyrrolo[2,3-d]pyrimidine was investigated. The newly synthesized compounds, except N-acetyl derivatives (Id, Ie, and Im), generally showed superior or similar activity against A375 to Sorafenib. Among all of these derivatives, compounds Iq and Ir having imidazole and morpholine moieties, respectively, showed the most potent antiproliferative activity against A375.

AB - Synthesis of a new series of diarylureas and amides having pyrrolo[2,3-d]pyrimidine scaffold is described. Their in vitro antiproliferative activities against A375 human melanoma cell line and HS 27 fibroblast cell line were tested and the effect of substituents on pyrrolo[2,3-d]pyrimidine was investigated. The newly synthesized compounds, except N-acetyl derivatives (Id, Ie, and Im), generally showed superior or similar activity against A375 to Sorafenib. Among all of these derivatives, compounds Iq and Ir having imidazole and morpholine moieties, respectively, showed the most potent antiproliferative activity against A375.

KW - A375

KW - Antiproliferative activity

KW - HS 27

KW - Melanoma

KW - Pyrrolo[2,3-d]pyrimidine

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Synthesis of pyrrolo[2,3-d]pyrimidine derivatives and their antiproliferative activity against melanoma cell line

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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