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Synthesis, anticancer evaluation and docking study of vadimezan derivatives with carboxyl substitutionElectronic supplementary information (ESI) available: Characterization data of all compounds. See DOI: 10.1039/c3md00372h
A series of xanthone analogues modified from vadimezan 6 with carboxyl substitution were synthesized as esters, amides, arylidene hydrazides, diacylhydrazides and acyl thiosemicarbazides, and their structures were confirmed by IR, 1 H NMR, MS, HRMS or elemental analysis. The in vitro anticancer acti...
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Main Authors: | , , , , , , |
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Format: | Article |
Language: | English |
Online Access: | Get full text |
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Summary: | A series of xanthone analogues modified from vadimezan
6
with carboxyl substitution were synthesized as esters, amides, arylidene hydrazides, diacylhydrazides and acyl thiosemicarbazides, and their structures were confirmed by IR,
1
H NMR, MS, HRMS or elemental analysis. The
in vitro
anticancer activities were evaluated by the MTT method. It was found that compounds
8f
,
8g
and
10e
were effective against A549 with an IC
50
at 10.8 μM, 9.4 μM and 11.5 μM respectively, and that
8e
was effective against HL-60 with an IC
50
at 4.6 μM. Compounds
8f-h
showed a significant inhibitory effect on HUVEC growth and migration
in vitro
, among which
8h
inhibited HUVEC growth with an IC
50
at 6.4 μM and HUVEC migration by 67.6% and 89.7% at 2.5 μg mL
−1
and 10 μg mL
−1
respectively. More spectacularly, docking study indicated that compound
8h
might target the ATP binding site of VEGFR2. In addition, compounds
8a
,
8f-h
exhibited moderate
in vivo
antitumor efficacy against the S180 xenograft in ICR mice by 22.4-29.6% tumor weight inhibition.
A series of xanthone analogues modified from vadimezan were synthesized and their anticancer activities were evaluated. |
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ISSN: | 2040-2503 2040-2511 |
DOI: | 10.1039/c3md00372h |