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Design, synthesis and antitumor activity of triterpenoid pyrazine derivatives from 23-hydroxybetulinic acid.

Abstract：

:Pyrazine-fused 23-hydroxybetulinic acid was synthesized by introducing a pyrazine ring between C-2 and C-3 position and further modifications were carried out by substitution of C-28 carboxyl group by ester and amide linkage to enhance the antitumor activity. The biological screening results showed that all of the derivatives exhibited more significant antiproliferative activity than the parent compound. In particular compound 12a exhibited the most potent activity with IC50 values of 3.53 μM, 4.42 μM and 5.13 μM against cell lines SF-763, B16 and Hela, respectively. In the preliminary mechanism study, 12a caused cell arrest in G1 phase and significantly induced apoptosis of B16 cells in a dose-dependent manner. Furthermore, the in vivo antitumor activity of 12a was validated (tumor inhibitory ratio of 55.6% and 62.7%, respectively) in mice with H22 liver cancer and B16 melanoma.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Zhang H,Wang Y,Zhu P,Liu J,Xu S,Yao H,Jiang J,Ye W,Wu X,Xu J

doi

10.1016/j.ejmech.2015.04.057

subject

Has Abstract

pub_date

2015-06-05 00:00:00

pages

235-44

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(15)30021-0

journal_volume

97

pub_type

杂志文章

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