A series of novel (-)-gossypol Schiff bases and hydrazones have been synthesized via an in-situ procedure in high yields. Structural data showed that all target compounds existed in enamine conformation. The bioassay result displayed that several compounds exhibited cytotoxic effects against three human cancer cell lines including HepG2, LU-1 and MCF-7 with IC50 values of 16.56, 10.75 and 7.44 µg/mL, respectively. In antibacterial test, some compounds also inhibited Staphylococcus aureus and Bacillus cereus at the same MIC values of 1024 µg/ml.
REFERENCES
1.
Howlader
, N.
; Noone
, A. M.
; Krapcho
, M.
; Garshell
, J.
; Miller
, D.
; Altekruse
, S. F.
; Kosary
, C L.
; Yu
, M.
; Ruhl
, J.
; Tatalovich
, Z.
; Mariotto
, A.
; Lewis
, D. R.
; Chen
, H. S.
; Feuer
, E. J.
; Cronin
, K. A
(eds). SEER Cancer Statistics Review
, 1975-2012, National Cancer Institute
. Bethesda, MD
, http://seer.cancer.gov/csr/1975_2012/, based on November 2014 SEER data submission, posted to the SEER web site, April 2015
.2.
Mellinghoff
, I. K.
; Sawyers
, C. L.
, Pharmacogenomics
. 3
, 603
–623
(2002
).3.
4.
Oliver
, C. L.
, Bauer
, J. A.
, Wolter
, K. G.
, Ubell
, M. L.
, Narayan
, A.
, O’Connell
, K. M.
, Fisher
, S. G.
, Wang
, S.
, Wu
, X.
, Ji
, M.
, Carey
, T. E.
, Bradford
, C. R.
, Clinical Cancer Res.
10
, 7757
–7763
(2004
).5.
Zhang
, M.
, Liu
, H.
, Tian
, Z.
, Griffith
, B. N.
, Ji
, M.
, Li
, Q. Q.
, Life Sci.
80
, 767
–774
(2007
).6.
Mohammad
, R. M.
, Wang
, S.
, Banerjee
, S.
, Wu
, X.
, Chen
, J.
, Sarkar
, F. H.
, Pancreas.
31
, 456
–457
(2005
).7.
Zhang
, M.
, Liu
, H.
, Guo
, R.
, Ling
, Y.
, Wu
, X.
, Li
, B.
, Roller
, P. P.
, Wang
, S.
, Yang
, D.
, Biochem. Pharmacol.
66
, 93
–103
(2003
).8.
D.W.
Hahn
., C.
Rusticus
., A.
Probst.
, R.
Homm
, A.N.
Johnson
., Contraception.
24
, 97
–105
(1981
).9.
Yang
, J.
, Chen
, G.
, Li
, L. L.
, Pan
, W.
, Zhang
, F.
, Yang
, J.
, Wu
, S.
, Tien
, P.
, Bioorg. Med. Chem. Lett.
23
, 2619
–2623
(2013
).10.
Yang
, J.
, Zhang
, F.
, Li
, J. R.
, Chen
, G.
, Wu
, S. W.
, Ouyang
, W. J.
, Pan
, W.
,Yu
, R.
, Yang
, J. X.
, Tien
, P.
, Bioorg. Med. Chem. Lett.
22
, 1415
–1420
(2012
).11.
Radloff
, R. J.
, Deck
, L. M.
, Royer
, R. E.
,Vander Jagt
, D. L.
, Pharmacol. Res. Commun.
18
, 1063
–1073
(1986
).12.
Tegos
, G.
, Stermitz
, F. R.
, Lomovskaya
, O.
, Lewis
, K.
, Antimicrob. Agents Chemother.
46
, 3133
–3141
(2002
).13.
Liang
, X. S.
, Rogers
, A. J.
, Webber
, C. L.
, Ormsby
, T. J.
,Tiritan
, M. E.
, Matlin
, S. A.
, Benz
, C. C.
, Invest. New Drugs.
13
, 181
–186
(1995
).14.
Royer
, R. E.
, Mills
, R. G.
, Deck
, L. M.
, Mertz
, G. J.
, Jagt
, D. L. V.
, Pharmacol. Res.
24
, 407
–412
(1991
).15.
a)
Lin
,T. S.
, Schinazi
,R. F.
, Zhu
,J.
, Birks
,E.
, Carbone
,R.
, Si
,Y.
, Wu
,K.
, Huang
,L.
, Pruwsoff
,W. H.
, Biochem. Pharmacol.
6
, 251
–255
(1993
);b)
Lu
,Y.
; Wu
,S.
; Yue
,Y.
; He
,S.
; Li
,J.
; Tang
,J.
; Wang
,W.
; Zhou
,H. B.
, Med. Chem. Lett.
7
, 1185
–1190
(2016
);c)
Li
,L.
; Li
,Z.
; Wang
,K.
; Zhao
,S.
; Feng
,J.
; Li
,J.
; Yang
,P.
; Liu
,Y.
; Wang
,L.
; Li
,Y.
; Shang
,H.
; Wang
,Q.
, J. Agric. Food Chem.
62
, 11080
–11088
(2014
);
[PubMed]
d)
Yonghua
, Z.
; Xu
, C.
; Yingchao
, L.
; Xueli
, C
; Xiaofeng
, H.
, Letters in Drug Design & Discovery
. 14
, 96
–101
(2017
).16.
Qiu
, J.
, Levin
, L. K.
, Buck
, J.
, Reidenberg
, M. M.
, Exp. Biol. Med.
227
, 398
–414
(2002
).17.
Tang
, G.
, Yang
, C. Y.
, Coleska
, Z. N.
, Guo
, J.
, Qiu
, S.
, Wang
, R.
, Gao
, W.
, Wang
, G.
, Stuckey
, J.
, Krajewski
, K.
, Jiang
, S.
, Roller
, P. P.
, Wang
, S.
, J. Med. Chem.
50
, 1723
–1726
(2007
).18.
Jiang
, H, X.
, Cao
, X. X.
, Huang
, H.
, Jiang
, B.
, Tetrahedron: Asymmetry
18
, 2437
–2441
(2007
).19.
Likhitwitayawid
K.
, Angerhof
C. K.
, Cordell
G.A.
, Nijsiri
R.
, and Pezutto
J.M.
, J. Nat. Prod.
56
, 30
–38
(1993
).20.
Kurekci
C
, Bishop-Hurley
SL
, Vercoe
PE
, Durmic
Z
, Al Jassim
RAM
, McSweeney
CS
., Phytother Res.
26
, 186
–90
(2012
).
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