Click approach to the discovery of 1,2,3-triazolylsalicylamides as potent Aurora kinase inhibitors

Doohee Song; Yunjeong Park; Jieun Yoon; Waqar Aman; Jung Mi Hah; Jae Sang Ryu

doi:10.1016/j.bmc.2014.06.047

Click approach to the discovery of 1,2,3-triazolylsalicylamides as potent Aurora kinase inhibitors

Doohee Song
, Yunjeong Park
, Jieun Yoon
, Waqar Aman
, Jung Mi Hah
, Jae Sang Ryu

Department of Pharmaceutical Sciences

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

12 Scopus citations

Abstract

A series of 1,2,3-triazolylsalicylamide derivatives has been developed from the antiproliferative agent 7 and was evaluated for their Aurora kinase inhibitory activity. The novel 1,2,3-triazolylsalicylamide scaffold could be readily assembled by Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition, allowing rapid access to the structurally diverse analogues. The synthesized 1,2,3-triazolylsalicylamide derivatives revealed a significant Aurora kinase inhibitory activity. In particular, 8g inhibited Aurora A with IC₅₀ values of 0.37 μM. The critical role of phenolic -OH in the binding was confirmed by a molecular modeling study.

Original language	English
Pages (from-to)	4855-4866
Number of pages	12
Journal	Bioorganic and Medicinal Chemistry
Volume	22
Issue number	17
DOIs	https://doi.org/10.1016/j.bmc.2014.06.047
State	Published - 1 Sep 2014

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( NRF-2012R1A2A2A01011831 ).

Keywords

1,2,3-Triazole
Anticancer
Aurora kinase
Click chemistry
Library

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10.1016/j.bmc.2014.06.047

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title = "Click approach to the discovery of 1,2,3-triazolylsalicylamides as potent Aurora kinase inhibitors",

abstract = "A series of 1,2,3-triazolylsalicylamide derivatives has been developed from the antiproliferative agent 7 and was evaluated for their Aurora kinase inhibitory activity. The novel 1,2,3-triazolylsalicylamide scaffold could be readily assembled by Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition, allowing rapid access to the structurally diverse analogues. The synthesized 1,2,3-triazolylsalicylamide derivatives revealed a significant Aurora kinase inhibitory activity. In particular, 8g inhibited Aurora A with IC50 values of 0.37 μM. The critical role of phenolic -OH in the binding was confirmed by a molecular modeling study.",

keywords = "1,2,3-Triazole, Anticancer, Aurora kinase, Click chemistry, Library",

author = "Doohee Song and Yunjeong Park and Jieun Yoon and Waqar Aman and Hah, \{Jung Mi\} and Ryu, \{Jae Sang\}",

note = "Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( NRF-2012R1A2A2A01011831 ). ",

year = "2014",

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doi = "10.1016/j.bmc.2014.06.047",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry",

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AU - Song, Doohee

AU - Park, Yunjeong

AU - Yoon, Jieun

AU - Aman, Waqar

AU - Hah, Jung Mi

AU - Ryu, Jae Sang

N1 - Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( NRF-2012R1A2A2A01011831 ).

PY - 2014/9/1

Y1 - 2014/9/1

N2 - A series of 1,2,3-triazolylsalicylamide derivatives has been developed from the antiproliferative agent 7 and was evaluated for their Aurora kinase inhibitory activity. The novel 1,2,3-triazolylsalicylamide scaffold could be readily assembled by Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition, allowing rapid access to the structurally diverse analogues. The synthesized 1,2,3-triazolylsalicylamide derivatives revealed a significant Aurora kinase inhibitory activity. In particular, 8g inhibited Aurora A with IC50 values of 0.37 μM. The critical role of phenolic -OH in the binding was confirmed by a molecular modeling study.

AB - A series of 1,2,3-triazolylsalicylamide derivatives has been developed from the antiproliferative agent 7 and was evaluated for their Aurora kinase inhibitory activity. The novel 1,2,3-triazolylsalicylamide scaffold could be readily assembled by Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition, allowing rapid access to the structurally diverse analogues. The synthesized 1,2,3-triazolylsalicylamide derivatives revealed a significant Aurora kinase inhibitory activity. In particular, 8g inhibited Aurora A with IC50 values of 0.37 μM. The critical role of phenolic -OH in the binding was confirmed by a molecular modeling study.

KW - 1,2,3-Triazole

KW - Anticancer

KW - Aurora kinase

KW - Click chemistry

KW - Library

UR - https://www.scopus.com/pages/publications/84906935513

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DO - 10.1016/j.bmc.2014.06.047

M3 - Article

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AN - SCOPUS:84906935513

SN - 0968-0896

VL - 22

SP - 4855

EP - 4866

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 17

ER -

Click approach to the discovery of 1,2,3-triazolylsalicylamides as potent Aurora kinase inhibitors

Abstract

Bibliographical note

Keywords

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