Synthesis, in vitro and in vivo antitumor activity of pyrazole-fused 23-hydroxybetulinic acid derivatives

Hengyuan Zhang; Peiqing Zhu; Jie Liu; Yan Lin; Hequan Yao; Jieyun Jiang; Wencai Ye; Xiaoming Wu; Jinyi Xu

doi:10.1016/j.bmcl.2014.11.058

Synthesis, in vitro and in vivo antitumor activity of pyrazole-fused 23-hydroxybetulinic acid derivatives

Hengyuan Zhang, Peiqing Zhu, Jie Liu, Yan Lin, Hequan Yao, Jieyun Jiang, Wencai Ye, Xiaoming Wu, Jinyi Xu

Microbiology, Immunology, and Molecular Genetics

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

32 Scopus citations

Abstract

A collection of pyrazole-fused 23-hydroxybetulinic acid derivatives were designed, synthesized and evaluated for their antitumor activity. Most of the newly synthesized compounds exhibited significant antiproliferative activity. Especially compound 15e displayed the most potent activity with the IC₅₀ values of 5.58 and 6.13 μM against B16 and SF763 cancer cell lines, respectively. Furthermore, the significant in vivo antitumor activity of 15e was validated in H22 liver cancer and B16 melanoma xenograft mouse models. The structure-activity relationships of these 23-hydroxybetulinic acid derivatives were also discussed based on the present investigation.

Original language	English
Pages (from-to)	728-732
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	25
Issue number	3
DOIs	https://doi.org/10.1016/j.bmcl.2014.11.058
State	Published - Feb 1 2015

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Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.

Keywords

23-Hydroxybetulinic acid
Antiproliferative activity
Antitumor activity
In vivo
Pyrazole

ASJC Scopus subject areas

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

UN SDGs

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

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10.1016/j.bmcl.2014.11.058

Cite this

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title = "Synthesis, in vitro and in vivo antitumor activity of pyrazole-fused 23-hydroxybetulinic acid derivatives",

abstract = "A collection of pyrazole-fused 23-hydroxybetulinic acid derivatives were designed, synthesized and evaluated for their antitumor activity. Most of the newly synthesized compounds exhibited significant antiproliferative activity. Especially compound 15e displayed the most potent activity with the IC50 values of 5.58 and 6.13 μM against B16 and SF763 cancer cell lines, respectively. Furthermore, the significant in vivo antitumor activity of 15e was validated in H22 liver cancer and B16 melanoma xenograft mouse models. The structure-activity relationships of these 23-hydroxybetulinic acid derivatives were also discussed based on the present investigation.",

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AU - Zhang, Hengyuan

AU - Zhu, Peiqing

AU - Liu, Jie

AU - Lin, Yan

AU - Yao, Hequan

AU - Jiang, Jieyun

AU - Ye, Wencai

AU - Wu, Xiaoming

AU - Xu, Jinyi

PY - 2015/2/1

Y1 - 2015/2/1

N2 - A collection of pyrazole-fused 23-hydroxybetulinic acid derivatives were designed, synthesized and evaluated for their antitumor activity. Most of the newly synthesized compounds exhibited significant antiproliferative activity. Especially compound 15e displayed the most potent activity with the IC50 values of 5.58 and 6.13 μM against B16 and SF763 cancer cell lines, respectively. Furthermore, the significant in vivo antitumor activity of 15e was validated in H22 liver cancer and B16 melanoma xenograft mouse models. The structure-activity relationships of these 23-hydroxybetulinic acid derivatives were also discussed based on the present investigation.

AB - A collection of pyrazole-fused 23-hydroxybetulinic acid derivatives were designed, synthesized and evaluated for their antitumor activity. Most of the newly synthesized compounds exhibited significant antiproliferative activity. Especially compound 15e displayed the most potent activity with the IC50 values of 5.58 and 6.13 μM against B16 and SF763 cancer cell lines, respectively. Furthermore, the significant in vivo antitumor activity of 15e was validated in H22 liver cancer and B16 melanoma xenograft mouse models. The structure-activity relationships of these 23-hydroxybetulinic acid derivatives were also discussed based on the present investigation.

KW - 23-Hydroxybetulinic acid

KW - Antiproliferative activity

KW - Antitumor activity

KW - In vivo

KW - Pyrazole

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Synthesis, in vitro and in vivo antitumor activity of pyrazole-fused 23-hydroxybetulinic acid derivatives

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

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