A rapid synthesis of lavendustin-mimetic small molecules by click fragment assembly

Jieun Yoon; Jae Sang Ryu

doi:10.1016/j.bmcl.2010.05.014

A rapid synthesis of lavendustin-mimetic small molecules by click fragment assembly

Jieun Yoon
, Jae Sang Ryu

Department of Pharmaceutical Sciences

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

32 Scopus citations

Abstract

Lavendustin-mimetic small molecules modifying the linker -CH ₂-NH- with an 1,2,3-triazole ring have been synthesized via a click chemistry. Two pharmacophoric fragments of lavendustin were varied to investigate chemical space and the auxophoric -CH₂-NH- was altered to an 1,2,3-triazole for rapid click conjugation. The small molecules were evaluated against HCT116 colon cancer and CCRF-CEM leukemia cell lines. Among 28 analogues, 3-phenylpropyl ester 26b inhibited CCRF-CEM leukemia cell growth with GI₅₀ value of 0.9 μM.

Original language	English
Pages (from-to)	3930-3935
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	13
DOIs	https://doi.org/10.1016/j.bmcl.2010.05.014
State	Published - 2010

Bibliographical note

Funding Information:
This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MOEHRD) ( KRF-2007-313-E00645 ). J.Y. was supported by the Brain Korea 21 project. Authors thank Hwayoung Yun and Dr. Seung-Mann Paek for mass spectroscopy.

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

Anticancer
Click chemistry
Lavendustin
Library
Triazole

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10.1016/j.bmcl.2010.05.014

Cite this

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title = "A rapid synthesis of lavendustin-mimetic small molecules by click fragment assembly",

abstract = "Lavendustin-mimetic small molecules modifying the linker -CH 2-NH- with an 1,2,3-triazole ring have been synthesized via a click chemistry. Two pharmacophoric fragments of lavendustin were varied to investigate chemical space and the auxophoric -CH2-NH- was altered to an 1,2,3-triazole for rapid click conjugation. The small molecules were evaluated against HCT116 colon cancer and CCRF-CEM leukemia cell lines. Among 28 analogues, 3-phenylpropyl ester 26b inhibited CCRF-CEM leukemia cell growth with GI50 value of 0.9 μM.",

keywords = "Anticancer, Click chemistry, Lavendustin, Library, Triazole",

author = "Jieun Yoon and Ryu, \{Jae Sang\}",

note = "Funding Information: This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MOEHRD) ( KRF-2007-313-E00645 ). J.Y. was supported by the Brain Korea 21 project. Authors thank Hwayoung Yun and Dr. Seung-Mann Paek for mass spectroscopy. ",

year = "2010",

doi = "10.1016/j.bmcl.2010.05.014",

language = "English",

volume = "20",

pages = "3930--3935",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

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T1 - A rapid synthesis of lavendustin-mimetic small molecules by click fragment assembly

AU - Yoon, Jieun

AU - Ryu, Jae Sang

N1 - Funding Information: This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MOEHRD) ( KRF-2007-313-E00645 ). J.Y. was supported by the Brain Korea 21 project. Authors thank Hwayoung Yun and Dr. Seung-Mann Paek for mass spectroscopy.

PY - 2010

Y1 - 2010

N2 - Lavendustin-mimetic small molecules modifying the linker -CH 2-NH- with an 1,2,3-triazole ring have been synthesized via a click chemistry. Two pharmacophoric fragments of lavendustin were varied to investigate chemical space and the auxophoric -CH2-NH- was altered to an 1,2,3-triazole for rapid click conjugation. The small molecules were evaluated against HCT116 colon cancer and CCRF-CEM leukemia cell lines. Among 28 analogues, 3-phenylpropyl ester 26b inhibited CCRF-CEM leukemia cell growth with GI50 value of 0.9 μM.

AB - Lavendustin-mimetic small molecules modifying the linker -CH 2-NH- with an 1,2,3-triazole ring have been synthesized via a click chemistry. Two pharmacophoric fragments of lavendustin were varied to investigate chemical space and the auxophoric -CH2-NH- was altered to an 1,2,3-triazole for rapid click conjugation. The small molecules were evaluated against HCT116 colon cancer and CCRF-CEM leukemia cell lines. Among 28 analogues, 3-phenylpropyl ester 26b inhibited CCRF-CEM leukemia cell growth with GI50 value of 0.9 μM.

KW - Anticancer

KW - Click chemistry

KW - Lavendustin

KW - Library

KW - Triazole

UR - https://www.scopus.com/pages/publications/77954310547

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DO - 10.1016/j.bmcl.2010.05.014

M3 - Article

C2 - 20570145

AN - SCOPUS:77954310547

SN - 0960-894X

VL - 20

SP - 3930

EP - 3935

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 13

ER -

A rapid synthesis of lavendustin-mimetic small molecules by click fragment assembly

Abstract

Bibliographical note

UN SDGs

Keywords

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