Abstract
A series of triazole derivatives of bergenin were synthesised through the nucleophilic substitution reaction of bergenin and propargyl bromide, and following click reaction with different azides. Their antitumour activities were evaluated against EC9706, MGC803 and B16 in vitro. Several compounds showed potent anti-tumour activity, especially (2S,3R,4R,4aS,10bR)-8,10-bis{{1-[4-(tert-butyl)benzyl]-1H-1,2,3-triazol-4-yl} methoxy}-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-2,3,4,4a-tetrahydropyrano[3,2-c]isochromen-6(10bH)-one, with IC50 value down to 6.28 μmol L-1 against EC970.
Get full access to this article
View all access options for this article.
References
1.
Levine
P.M.
,
Garabedian
M. J.
, and
Kirshenbaum
K.
, J. Med. Chem. , 2014 , 57 , 8224 .
2.
Wall
M.E.
,
Wani
M. C.
,
Cook
C. E.
,
Palmer
K. H.
,
McPhail
A. T.
, and
Sim
G. A.
J. Am. Chem. Soc. , 1966 , 88 , 3888 .
3.
Skwarczynski
M.
,
Hayashi
Y.
, and
Yoshiaki
K.
, J. Med. Chem. , 2006 , 49 , 7253 .
4.
Sharma
V.
,
Köllmer
M.
,
Szymusiak
M.
,
Nitsche
L. C.
,
Gemeinhart
R. A.
, and
Liu
Y.
, Biomacromolecules , 2014 , 15 , 756 .
5.
Skwarczynski
M.
,
Hayashi
Y.
, and
Yoshiaki
K.
, Bioconjugate Chem. , 2011 , 22 , 2474 .
6.
Bahl
C.P.
,
Murari
R.
,
Parthasarathy
M. R.
, and
Seshadri
T. R.
, Indian J. Chem. 1974 , 12 , 1038 .
7.
Taneyama
M.
,
Yoshida
S.
, and
Kobayashi
M.
, Phytochemistry , 1983 , 22 , 1053 .
8.
Jahromi
M.A. F.
,
Chansouri
J. P. N.
, and
Ray
A. B.
, Phytother. Res. , 1992 , 6 , 180 .
9.
Piacente
S.
,
Pizza
C.
, and
De Tommasi
N.
, J. Nat. Prod. , 1996 , 59 , 565 .
10.
Swarnalakshmi
T.
,
Sethuraman
M. G.
,
Sulochana
N.
, and
Arivudainambi
R.
, Curr. Sci. , 1984 , 53 , 917 .
11.
Takahashi
H.
,
Kosaka
M.
,
Watanabe
Y.
,
Nakade
K.
, and
Fukuyama
Y.
, Bioorg. Med. Chem. , 2003 , 11 , 1781 .
12.
Pu
H.L.
,
Huang
X.
,
Zhao
J. H.
, and
Hing
A.
, Planta Med. , 2002 , 68 , 372 .
13.
Lim
H.K.
,
Kim
H. S.
,
Choi
H. S.
,
Oh
S.
, and
Choi
J.
, J. Ethnopharmacol , 2000 , 72 , 469 .
14.
Goel
R.K.
,
Maiti
R. N.
,
Manickam
M.
, and
Ray
A. B.
, Indian J. Exp. Biol. , 1997 , 35 , 1080 .
15.
Sanghvi
Y.S.
,
Bhattacharya
B. K.
,
Kini
G. D.
,
Matsumoto
S. S.
,
Larson
S. B.
,
Jolley
W. B.
,
Robins
R. K.
, and
Revankar
G. R.
, J. Med. Chem. , 1990 , 33 , 336 .
16.
Zhu
X.F.
,
Chen
X. B.
,
Yan
M.
,
Shi
D. Q.
, and
Ding
K. R.
, Heteroat. Chem. , 2008 , 19 , 15 .
17.
Aufort
M.
,
Herscovici
J.
,
Bouhours
P.
,
Moreau
N.
, and
Girard
C.
, Bioorg. Med. Chem. Lett. , 2008 , 18 , 1195 .
18.
Gallardo
H.
,
Conte
G.
,
Bryk
F.
,
Lourenco
M. C. S.
,
Costa
M. S.
, and
Ferreira
V. F.
, J. Bras. Chem. Soc. , 2007 , 18 , 1285 .
19.
Banu
K.M.
,
Dinakar
A.
, and
Ananthanarayanan
C.
, Indian J. Pharm Sci. , 1999 , 4 , 202 .
20.
Jilino
M.
, and
Stevens
M. F. G.
, J. Chem. Soc. Perkin. Trans. 1 , 1998 , 1677 .
21.
Kamal
A.
,
Sankaraiah
N.
,
Devaiah
V.
,
Reddy
K. L.
,
Juvekar
A.
,
Sen
S.
,
Kunan
N.
, and
Zingde
S.
, Bioorg. Med. Chem. Lett. , 2008 , 18 , 1468 .
22.
Thirumurugan
P.
,
Matosiuk
D.
, and
Jozwiak
K.
, Chem. Rev. , 2013 , 113 , 4905 .
23.
Skehan
P.
,
Storeng
R.
,
Scudiero
D.
,
Monks
A.
,
McMahon
J.
,
Vistica
D.
,
Warren
J. T.
,
Bokesch
H.
,
Kenney
S.
, and
Boyd
M. R.
, J. Natl. Cancer Inst. , 1990 , 82 , 1107 .