Synthesis and evaluation of the HIF-1α inhibitory activities of novel ursolic acid tetrazole derivatives
1
Key Laboratory of Natural Resources of Changbai Mountain and Functional Molecules, Ministry of Education, Yanbian University College of Pharmacy, Yanji, 133002, China.
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Publication type: Journal Article
Publication date: 2019-06-01
scimago Q2
wos Q2
SJR: 0.472
CiteScore: 5.1
Impact factor: 2.2
ISSN: 0960894X, 14643405
PubMed ID:
31006525
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Abstract
The hypoxia-inducible factor-1α (HIF-1α) pathway has been implicated in tumor angiogenesis, growth, and metastasis. Therefore, the inhibition of this pathway is an important therapeutic target for the treatment of various types of cancers. Here, we designed and synthesized 31 ursolic acid (UA) derivatives containing a tetrazole moiety and evaluated them for their potential anti-tumor activities as HIF-1α transcriptional inhibitors. Of these, compound 14d (IC50 0.8 ± 0.2 µM) displayed the most potent activity and compounds 14a (IC50 4.7 ± 0.2 µM) exhibited the most promising biological profile. Analysis of the structure-activity relationships of these compounds with HIF-1α suggested that the presence of a tetrazole group located at C-28 of the UA derivatives was critical for their inhibitory activities.
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Total citations:
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Citations from 2025:
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(11.54%)
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MLA
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GOST
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Zhang L. et al. Synthesis and evaluation of the HIF-1α inhibitory activities of novel ursolic acid tetrazole derivatives // Bioorganic and Medicinal Chemistry Letters. 2019. Vol. 29. No. 12. pp. 1440-1445.
GOST all authors (up to 50)
Copy
Zhang L., Zhang Z., Li M. Y., Wei Z., Jin X., Piao H. Synthesis and evaluation of the HIF-1α inhibitory activities of novel ursolic acid tetrazole derivatives // Bioorganic and Medicinal Chemistry Letters. 2019. Vol. 29. No. 12. pp. 1440-1445.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.bmcl.2019.04.028
UR - https://doi.org/10.1016/j.bmcl.2019.04.028
TI - Synthesis and evaluation of the HIF-1α inhibitory activities of novel ursolic acid tetrazole derivatives
T2 - Bioorganic and Medicinal Chemistry Letters
AU - Zhang, Lin-Hao
AU - Zhang, Zhi-Hong
AU - Li, Ming Yue
AU - Wei, Zhi-Yu
AU - Jin, Xue-Jun
AU - Piao, Hu-Ri
PY - 2019
DA - 2019/06/01
PB - Elsevier
SP - 1440-1445
IS - 12
VL - 29
PMID - 31006525
SN - 0960-894X
SN - 1464-3405
ER -
Cite this
BibTex (up to 50 authors)
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@article{2019_Zhang,
author = {Lin-Hao Zhang and Zhi-Hong Zhang and Ming Yue Li and Zhi-Yu Wei and Xue-Jun Jin and Hu-Ri Piao},
title = {Synthesis and evaluation of the HIF-1α inhibitory activities of novel ursolic acid tetrazole derivatives},
journal = {Bioorganic and Medicinal Chemistry Letters},
year = {2019},
volume = {29},
publisher = {Elsevier},
month = {jun},
url = {https://doi.org/10.1016/j.bmcl.2019.04.028},
number = {12},
pages = {1440--1445},
doi = {10.1016/j.bmcl.2019.04.028}
}
Cite this
MLA
Copy
Zhang, Lin-Hao, et al. “Synthesis and evaluation of the HIF-1α inhibitory activities of novel ursolic acid tetrazole derivatives.” Bioorganic and Medicinal Chemistry Letters, vol. 29, no. 12, Jun. 2019, pp. 1440-1445. https://doi.org/10.1016/j.bmcl.2019.04.028.