Novel 2′-hydroxylfurylchalcones: Synthesis and biological activity

Article abstract of DOI:10.1016/j.carres.2010.05.017

Twelve novel 2′-hydroxylfurylchalcones have been synthesized by Claisen-Schmidt condensation with galactosylisomaltol, a reagent prepared from lactose. The procedures are environmentally benign and economical. All the compounds are identified by IR, ¹H NMR and ¹³C NMR spectroscopy and by mass spectrometry. Preliminary bioassays indicate that all the title compounds show moderately high herbicidal activities against the height and/or the fresh weight of the seedlings of cucumber, rape, amaranth, wheat, sorghum and Chinese sprangletop at 7.5 g of active ingredient per hm ². However, the compounds exhibit weak fungicidal activities against cucumber powdery mildew, and no activities against rice blast, cucumber grey mould and cucumber downy mildew. The structure-activity relationships are discussed. The present work demonstrates that 2′-hydroxylfurylchalcones could be used as potential lead compounds for further study of novel herbicides.

Full text of DOI:10.1016/j.carres.2010.05.017

Carbohydrate Research 345 (2010) 1872–1876
Contents lists available at ScienceDirect
Carbohydrate Research
journal homepage: www.elsevier.com/locate/carres
Novel 20-hydroxylfurylchalcones: synthesis and biological activity
*
Yunfei Deng , Yuan He , Taisong Zhan, Qingchun Huang
State Key Laboratory of Bioreactor Engineering, Shanghai Key Laboratory of Chemical Biology, School of Pharmacy,
East China University of Science and Technology, Shanghai 200237, China
a r t i c l e i n f o
a b s t r a c t
Twelve novel 20-hydroxylfurylchalcones have been synthesized by Claisen–Schmidt condensation with
galactosylisomaltol, a reagent prepared from lactose. The procedures are environmentally benign and
economical. All the compounds are identified by IR, 1H NMR and 13C NMR spectroscopy and by mass
spectrometry. Preliminary bioassays indicate that all the title compounds show moderately high herbi-
cidal activities against the height and/or the fresh weight of the seedlings of cucumber, rape, amaranth,
wheat, sorghum and Chinese sprangletop at 7.5 g of active ingredient per hm2. However, the compounds
exhibit weak fungicidal activities against cucumber powdery mildew, and no activities against rice blast,
cucumber grey mould and cucumber downy mildew. The structure–activity relationships are discussed.
The present work demonstrates that 20-hydroxylfurylchalcones could be used as potential lead com-
pounds for further study of novel herbicides.
Article history:
Received 26 November 2009
Received in revised form 18 May 2010
Accepted 19 May 2010
Available online 23 May 2010
Keywords:
20-Hydroxylfurylchalcone
Herbicides
Antifungal activity
Ó 2010 Elsevier Ltd. All rights reserved.
1. Introduction
galactosylisomaltol can then be condensed with aldehydes to
generate chalcone-like compounds,6 we designed the general
Chalcones, the precursors of flavonoids, are widely distributed
in edible plants such as vegetables, fruits, spices, tea and soy-based
foodstuffs.1 Hydroxylated chalcones mostly exhibit free-radical
quenching properties, and therefore display many biological activ-
ities, for example, anti-inflammatory, antimicrobial, antifungal,
antioxidant, cytotoxic, antitumour and anticancer activities.2 The
development of chalcone-based drugs has been given considerable
attention recently.3 Chemically they consist of open-chain flavo-
noids in which the two aromatic rings are joined by a three-carbon
structure C that was spliced by active groups of 2-acetyl-3-
methoxyfuran and chalcone for the purpose of obtaining an opti-
mized compound with improved biological activity. Twelve new
20-hydroxylfurylchalcones were then synthesized (Scheme 1).
Interestingly, some compounds did not show antifungal activity,
but revealed good herbicidal activities. This research to some de-
gree extends the knowledge of the physicochemical and biological
properties of novel chalcones as potential herbicides. Herein, the
synthesis of these 20-hydroxylfurylchalcones is reported as shown
in Scheme 1. Antifungal activity in vivo and whole plant herbicidal
activity are determined, and the primary structure–activity rela-
tionships among those novel compounds are also discussed.
a,b-unsaturated carbonyl system (structure A). The structural
modifications on the two aromatic rings provide some structural
bases for different activities.4
2-Acetyl-3-methoxyfuran (structure B), a secondary metabolite
that was purified from the broth of Actinomycete SPRI-10304,
showed considerable control efficiency against cucumber powdery
mildew (Erysiphe cichoracearum). Its bioisosteric structure was pre-
sumed to be very similar to that of methoxyacrylic acid, a well-
known strobilurins fungicide.5 It is of interest to carry out further
structural modifications to generate potential intermediates for
improving pesticide activity. Galactosylisomaltol, a water-soluble,
nonvolatile, nonenzymic browning product that is formed by the
action of free amino acids during the bread-baking process, is
chemically prepared by the condensation of lactose and maltose
with secondary amino acids. Since the active methyl groups on
OH
O
O
R'
R"
O
R
O
O
O
A
B
C
2. Results and discussion
Many biologically active agents are usually discovered by either
of two methods: (i) mass screening or (ii) chemical modification of
diverse natural products. Those with antifungal activity, such as
nereistoxins and strobilurins, have been exploited as excellent
pesticides to protect crops from the damages caused by field
* Corresponding author. Tel: +86 21 6425 2945; fax: +86 21 6425 2603.
E-mail address: qchuang@ecust.edu.cn (Q. Huang).
Co-first author.
pests.7 Indeed, (E)-1-(30-O-b-
D
-galactopyranosyloxy-20-furanyl)-3-
(300-hydroxy-400-methoxyphenyl)-2-propen-1-one was previously
0008-6215/$ - see front matter Ó 2010 Elsevier Ltd. All rights reserved.
doi:10.1016/j.carres.2010.05.017

Y. Deng et al. / Carbohydrate Research 345 (2010) 1872–1876
1873
HO
OH
OH
O
O
OH
OH
HO
O
piperidine, AcOH
O
O
O
O
OH
HO
HO
EtOH, N(C2H5)3
OH
OH
OH
+
OH
(1) H2O/EtOH/NaOH overnight
R
CHO
R
O
(2)
10% HCl rt
O
CH
3
OCH3
Cl
5: R =
1: R =
2: R =
3: R =
9: R =
4: R =
6: R =
O
N
CN
Cl
Br
F
7: R =
8: R =
12: R =
10: R =
11: R =
NO2
Cl
Scheme 1. General synthetic route for the title compounds (1–12).
synthesized by the aldol condensation of galactosylisomaltol with
isovanillin and acid hydrolysis in a yield of 53.9%.6 We improved
the efficiency of the reaction by direct Claisen–Schmidt condensa-
tion and the hydrolysis of the galactosyl moiety in one step under
alkaline conditions and obtained 20-hydroxylfurylchalcones in
yields of 63–84% within 24 h at room temperature. There was no
need to protect the hydroxyl groups, and ethanol and water were
used as solvents. All title compounds were characterized by IR,
NMR (1H, 13C and COSY) spectroscopy and by mass spectrometry.
The purity was established by TLC and microanalysis. The stereo-
chemistry around the olefinic carbon–carbon bond was established
using the corresponding 1H NMR coupling constant.6
Antifungal and antibacterial activities of chalcones have been
well documented. Licochalcone A shows antibacterial activity
against spore-forming bacteria.8 5-Methylfuryl chalcones and 5-
nitrofuryl chalcones that were modified from the structure of
daphneolone show significant in vitro anti-plant pathogenic fungi
activities.9 Bioassays showed that the 20-hydroxylfurylchalcones
(1–12) possessed less than 10% control efficiency on cucumber
powdery mildew and no activities on rice blast, cucumber grey
mould and cucumber downy mildew (data not shown). However,
most of them showed broad-spectrum and high herbicidal activi-
ties in postemergence treatments against three monocotyledonous
and three dicotyledonous plants. Data are shown in Tables 1 and 2.
Although the 20-hydroxylfurylchalcones did not block seed germi-
nation, the growth of all seedlings was inhibited, their stems were
slender and thin, and their fresh weight was decreased signifi-
cantly. Compound 7 exhibited the highest inhibitory rate with
about 56.8% against the seedling height of Cucumis sativus, and
11 showed the strongest activity against the fresh weight gain of
Amaranthus mangostanus seedlings at a rate of 90.6%. In case of
Leptochloa chinensis seedlings, the 20-hydroxylfurylchalcones did
not affect their height significantly, but 8 showed an inhibitory rate
of 66.7% on its fresh weight gain. Obviously, the 20-hydroxylfuryl-
chalcones possessed higher activity against dicotyledons and less
activity against monocotyledons than that of a commercial herbi-
cide, haloxyfop-p-methyl, (methyl (R)-2-{4-[3-chloro-5-(trifluoro-
methyl)-2-pyridyloxy]phenoxy}propionate).
As substituent R is the only variable in the structure of the 20-
hydroxylfurylchalcones, its steric and electrostatic properties are
naturally the most significant factors in determining the herbicidal
activity. Activities of the compounds differ so much among individ-
ual plants that practically no definite conclusion regarding the
relationship between structure and biological activity can be made
at the present time. Nonetheless, in dicotyledonous plants the
highest potencies were exhibited with compounds 4 and 8–12.
The high activity of naphthalene-2-yl derivative (11) could be the
result of its high lipophilicity. Good activities of compounds 8–10
and 12 are in agreement with other reports that confirm the posi-
tive influence of electron-withdrawing groups (EWG) on the bio-
logical activities of chalcones.10 In derivative 4, the oxygen atom
in the furan ring probably behaves as an EWG. Compound 3, which
has an electron-withdrawing cyano group in the meta-position,
was not a very strong inhibitor. This could be explained by the
Table 1
Average inhibitory rates (% control) of 12 title compounds against three dicotyledons C. sativus, B. campestris and A. mangostanus at 15 days post-treatment
Chemicals
Concentrations
(g a.i./hm2)a
C. sativus
Fresh weight
B. campestris
Fresh weight
A. mangostanus
Fresh weight
Substituted moieties
Height
Height
Height
1
2
3
4
5
6
7
8
C6H5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
33.7
31.0
33.3
36.1
32.7
33.3
56.8
40.5
35.1
46.8
41.3
36.5
42.1
1.3
33.1
13.7
49.7
39.3
35.3
17.5
34.5
37.3
40.6
44.0
68.2
31.5
38.1
52.4
14.3
38.1
33.3
38.1
19.0
52.4
42.9
52.4
52.4
52.4
44.4
60.3
31.8
ꢀ5.9
82.1
45.9
72.3
15.1
66.7
87.2
85.9
72.9
83.5
17.2
18.8
18.8
37.5
12.5
12.5
37.5
6.3
37.5
18.8
25.0
37.5
37.5
2.1
32.6
23.9
31.7
69.6
72.2
54.8
24.3
71.7
69.6
74.8
90.6
81.2
21.6
2-C5H4N
3-CNC6H4
2-C4H3O
4-CH3C6H4
4-OCH3C6H4
4-FC6H4
4-BrC6H4
2,4-Cl2C6H3
3-NO2C6H4
2-C10H7
9
10
11
12
4-ClC6H4
Haloxyfop-p-methyl
a
a.i.: Active ingredient.

1874
Y. Deng et al. / Carbohydrate Research 345 (2010) 1872–1876
Table 2
a
Average inhibitory rates (% control) of 12 title compounds against three monocotyledons T. aestivum, S. vulgare and L. chinensis at 15 days post-treatment
Chemicals
Concentrations
(g a.i./hm2)b
T. aestivum
Fresh weight
S. vulgare
Fresh weight
L. chinensis
Fresh weight
Substituted moieties
Height
Height
Height
1
2
3
4
5
6
7
8
C6H5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
7.5
37.2
37.0
30.5
24.4
28.1
35.4
37.0
42.5
39.5
33.9
27.1
41.8
100.0
46.2
40.9
36.1
49.6
53.0
53.3
40.6
64.2
63.4
52.5
45.4
64.6
100.0
55.3
13.6
34.0
4.0
36.0
11.3
24.0
12.4
32.3
ND
ND
ND
ND
ND
ND
ND
100.0
ꢀ4.4
6.7
ꢀ12.3
ꢀ3.2
ꢀ10.1
2.1
31.3
37.4
12.4
56.1
47.8
60.4
19.0
66.7
57.1
63.1
55.9
52.6
100.0
2-C5H4N
3-CNC6H4
2-C4H3O
4-CH3C6H4
4-OCH3C6H4
4-FC6H4
4-BrC6H4
2,4-Cl2C6H3
3-NO2C6H4
2-C10H7
ꢀ3.8
ND
ND
ND
ND
ND
ND
ND
100.0
3.5
4.2
9
ꢀ0.7
10
11
12
1.4
ꢀ7.4
ꢀ3.9
100.0
4-ClC6H4
Haloxyfop-p-methyl
a
ND: Not determined.
a.i.: Active ingredient.
b
polar character of the CN group. In monocotyledonous plants, the
results are less consistent, but relationships similar to those for
dicotyledonous plants can be observed as well.
In summary, the convenience of the synthetic method and the
herbicidal activity of the title compounds, novel synthetic 20-
hydroxylfurylchalcones, suggest that they could be used as possi-
ble lead compounds for further developing new herbicides for
use in agriculture.
(400 MHz, DMSO-d6): d 7.81 (d, J 2.0 Hz, 1H), 7.70 (d, J 1.6 Hz,
1H), 7.68 (d, J 1.6 Hz, 1H), 7.65 (d, J 6.0 Hz, 2H), 7.43–7.48 (m,
3H), 6.42 (d, J 2.0 Hz, 1H); 13C NMR (100 MHz, DMSO-d6): d
175.2, 154.6, 148.6, 141.0, 137.3, 135.2, 130.6, 129.5, 106.7;
HREIMS: calcd for C13H10O3 (M+), 214.0630; found: 214.0629.
3.2.2. (2E)-1-(3-Hydroxyfuran-2-yl)-3-(pyridin-2-yl)prop-2-en-
1-one (2)
Yield: 68%. Yellow solid, mp 189–191 °C; IR(KBr)
mmax: 3011,
2528, 1648, 1583, 1454, 1004, 782 cmꢀ1 1H NMR (400 MHz,
;
3. Experimental
DMSO-d6): d 8.66 (d, J 4.0 Hz, 1H), 8.07 (d, J 15.6 Hz, 1H), 7.81–
7.87 (m, 2H), 7.68 (d, J 5.6 Hz, 1H), 7.63 (s, 1H), 7.40 (t, J 6.4 Hz,
1H), 6.41 (s, 1H); 13C NMR (100 MHz, DMSO-d6): d 171.5, 155.2
(d, J 22.8 Hz), 153.2, 150.4, 149.2 (d, J 24.0 Hz), 140.1, 137.7,
137.4, 126.9, 125.6, 124.9, 106.7; HREIMS: calcd for C12H9NO3
(M+), 215.0582; found: 215.0585.
3.1. Instruments and reagents
Melting points were obtained via a Büchi Melting Point B-540
apparatus (Büchi Labortechnik AG, Switzerland) and are
uncorrected. 1H and 13C NMR spectra were performed on a Bruker
AM-400 (400 MHz) spectrometer in CDCl3, DMSO or acetone with
tetramethylsilane as the internal standard. The chemical shifts are
reported in parts per million (ppm). EI high-resolution mass
spectra (HREIMS) were carried out with a MicroMass GCT CA055
spectrometer. The reagents and solvents were commercially avail-
able and were purified by conventional methods. Only those com-
pounds with purity around 95% were tested for biological activity.
3.2.3. 3-[(1E)-3-(3-Hydroxyfuran-2-yl)-3-oxoprop-1-en-1-
yl]benzonitrile (3)
Yield: 63%. Pale-yellow solid, mp 162–163 °C; IR(KBr) mmax
:
2612, 2224, 1642, 1476, 1080, 878 cmꢀ1 1H NMR (400 MHz,
;
DMSO-d6): d 8.16 (s, 1H), 8.02 (d, J 7.6 Hz, 1H), 7.86 (d, J 7.6 Hz,
1H), 7.82 (s, 1H), 7.62–7.72 (m, 3H), 6.41 (s, 1H); 13C NMR
(100 MHz, DMSO-d6): d 174.8, 155.1, 148.9, 138.7, 137.3, 136.6,
133.6, 132.6, 132.3, 130.6, 125.8, 118.8, 112.6, 106.8; HREIMS:
calcd for C14H9NO3 (M+), 239.0582; found: 239.0579.
3.2. General procedure for the syntheses of title compounds
Galactosylisomaltol
(3-O-b-D-galactopyranosyloxy-2-furanyl
methyl ketone) was prepared by the method of Hodge et al.6 A Cla-
isen–Schmidt condensation with NaOH was used to synthesize the
title compounds (Scheme 1) by reacting the galactosylisomaltol
with appropriate aryl aldehydes.11 None of the compounds have
been reported before.
3.2.4. (2E)-3-(Furan-2-yl)-1-(3-hydroxyfuran-2-yl)prop-2-en-1-
one (4)
Yield: 79%. Yellow crystals, mp 164–166 °C; IR (KBr) mmax: 3018,
2644, 1710, 1518, 1390, 1091 cmꢀ1; 1H NMR (400 MHz, DMSO-d6):
d 7.84 (s, 1H), 7.78 (s, 1H), 7.39–7.49 (m, 2H), 6.93 (d, J 2.8 Hz, 1H),
6.63 (s, 1H), 6.39 (s, 1H); 13C NMR (100 MHz, DMSO-d6): d 174.8,
154.4, 151.6, 148.5, 146.0, 137.3, 127.7, 120.7, 116.5, 113.3,
To a mixture of galactosylisomaltol (0.58 g, 2.0 mmol) and aryl
aldehydes (2.0 mmol) in EtOH (15 mL) was added dropwise a solu-
tion of NaOH (4.8 g, 12.0 mmol) in water (10 mL) with stirring. The
reaction mixture was stirred at room temperature for 12 h. When
the reaction was complete, most of the EtOH was removed by vac-
uum distillation, and ice-cold water (15 mL) was added. The mix-
106.7; HREIMS: Calcd for
204.0422.
C
11H8O4 (M+), 204.0423; found:
ture was neutralized by HCl (2.0 mol Lꢀ1
) with continuous
3.2.5. (2E)-1-(3-Hydroxyfuran-2-yl)-3-(4-methylphenyl)prop-2-
stirring. The precipitated product was dried by vacuum filtration
to give a yellow solid. Recrystallization from EtOH or N,N-dimeth-
ylformamide (DMF) gave the desired compounds.
en-1-one (5)
Yield: 65%. Yellow needles, mp 126–127 °C; IR (KBr) mmax: 2966,
2629, 1642, 1538, 1460, 1246, 1091, 810 cmꢀ1; 1H NMR (400 MHz,
DMSO-d6): d 7.78 (s, 1H), 7.55–7.66 (m, 4H), 7.25 (d, J 7.6 Hz, 2H),
6.41 (s, 1H), 2.34 (s, 3H); 13C NMR (100 MHz, DMSO-d6): d 174.8,
155.1, 148.9, 138.7, 137.3, 136.6, 133.6, 132.6, 132.3, 130.6,
125.8, 118.8, 112.6, 106.8; HREIMS: calcd for C14H12O3 (M+),
228.0786; found: 228.0789.
3.2.1. (2E)-1-(3-Hydroxyfuran-2-yl)-3-phenylprop-2-en-1-one
(1)
Yield: 71%. Yellow crystalline solid, mp 108–109 °C; IR (KBr)
mmax
: ;
3028, 2634, 1640, 1538, 1468, 1091 cmꢀ1 1H NMR

Y. Deng et al. / Carbohydrate Research 345 (2010) 1872–1876
1875
3.2.6. (2E)-1-(3-Hydroxyfuran-2-yl)-3-(4-methoxyphenyl)prop-
5.2 Hz, 1H), 7.50 (d,
J
8.0 Hz, 1H), 6.41 (s, 1H); 13C NMR
2-en-1-one (6)
(100 MHz, DMSO-d6): d 177.2, 166.7, 154.7, 151.5, 139.5, 134.3,
Yield: 71%. Yellow crystalline solid, mp 108–109 °C; IR (KBr)
131.5, 130.7, 130.6, 123.4, 116.5, 116.3, 107.0. HREIMS: calcd for
C
C
m
max: 3062, 2579, 1721, 1577, 1750, 1321, 1151, 802 cmꢀ1
;
1H
13H935ClO3 (M+), 248.0216; found: 248.0217; calcd for
13H937ClO3 (M+), 250.0246; found: 250.0297.
NMR (400 MHz, DMSO-d6): d 7.77 (s, 1H), 7.63 (t, J 8.0 Hz, 3H),
7.48 (d, J 16.0 Hz, 1H), 7.01 (d, J 8.8 Hz, 2H), 6.40 (s, 1H), 3.80 (s,
3H); 13C NMR (100 MHz, DMSO-d6): d 175.6, 161.4, 154.3, 148.2,
141.1, 137.3, 130.4, 127.8, 121.1, 115.0, 106.7, 55.8; HREIMS: calcd
for C14H12O4 (M+), 244.0736; found: 244.0737.
3.3. Biological activity assays
3.3.1. In vivo assays for fungicidal activity
In vivo assays were investigated on four plant diseases such as
rice blast (Magnaporthe grisea), cucumber grey mould (Botrytis
cinerea), cucumber downy mildew (Pseudoperonospora cubensis)
and cucumber powdery mildew (E. cichoracearum). The detailed
procedures were according to those in the previous reports.12
The compounds were dissolved in DMF and emulsified by water
containing Triton X-100 (0.2 mL Lꢀ1) at a range of concentrations,
and then the solutions were sprayed onto plants. Fungal spores
were inoculated on the plant leaf at 1 day after treating with the
compounds. The same treatments that were sprayed and inocu-
lated with the appropriate solvents, only, were utilized as controls.
3.2.7. (2E)-3-(4-Fluorophenyl)-1-(3-hydroxyfuran-2-yl)prop-2-
en-1-one (7)
Yield: 84%. Yellow crystalline solid, mp 143–144 °C; IR (KBr)
m
max: 3129, 2640, 1642, 1603, 1479, 1243, 818 cmꢀ1 1H NMR
;
(400 MHz, acetone-d6): d 7.73–7.79 (m, 3H), 7.66 (d, J 15.6 Hz,
1H), 7.56 (d, J 16.0 Hz, 1H), 7.25–7.29 (m, 2H), 6.51 (s, 1H); 13C
NMR (100 MHz, acetone-d6): d 175.2, 164.7, 154.7, 148.5, 139.8,
137.3, 131.9, 130.8, 130.7, 123.4, 116.5, 116.3, 106.7; HREIMS:
calcd for C13H9FO3 (M+), 232.0536; found: 232.0539.
3.2.8. (2E)-3-(4-Bromophenyl)-1-(3-hydroxyfuran-2-yl)prop-2-
en-1-one (8)
3.3.2. Whole plant assays on herbicidal activity
Yield: 72%. Yellow crystalline solid, mp 199–201 °C; IR (KBr)
A seedling assay on 2% agar medium was made for rapidly eval-
uating the activities of these compounds as herbicides according to
the method of Burke et al. with minor modification.13 The stock
solution of the compounds dissolved with DMF was added to the
melting medium by making the final doses at 7.5 g a.i./hm2. The
seeds of C. sativus, Brassica campestris, A. mangostanus, Triticum aes-
tivum, Sorghum vulgare and L. chinensis were inoculated on the
medium for 15 days under sunlight, and then the seedling height
and the seedling fresh weight were measured. Each treatment
was replicated three times. The same treatment without test com-
pounds was used as a control. Inhibitory rates were calculated by
referring to the control as in the following formula:
m
max: 3123, 2685, 1634, 1485, 875, 810 cmꢀ1 1H NMR (400 MHz,
;
DMSO-d6): d 7.83–7.89 (m, 4H), 7.73 (s, 1H), 7.65 (d, J 16.0 Hz,
1H), 7.51 (d, J 8.4 Hz, 1H), 6.41 (s, 1H); 13C NMR (100 MHz,
DMSO-d6): d 174.4, 155.3, 149.2, 137.3, 135.5, 135.1, 134.7,
132.1, 130.0, 129.6, 128.6, 127.0, 106.7; HREIMS: calcd for
C
13H9BrO3 (M+), 293.9730; found: 293.9731.
3.2.9. (2E)-3-(2,4-Dichlorophenyl)-1-(3-hydroxyfuran-2-
yl)prop-2-en-1-one (9)
Yield: 70%. Yellow crystalline solid, mp 177–179 °C; IR (KBr)
m
max: 2990, 2542, 1592, 1701, 1499, 1313, 856, 722 cmꢀ1 1H
;
NMR (400 MHz, CDCl3): d 8.20 (d, J 16.0 Hz, 1H), 7.69 (d, J 8.8 Hz,
1H), 7.47–7.57 (m, 2H), 7.39 (s, 1H), 7.23–7.31 (m, 1H), 6.36 (s,
1H); 13C NMR (100 MHz, CDCl3): d 166.0, 147.0, 138.0, 136.8,
136.6, 136.2, 132.2, 130.1, 129.8, 128.4, 127.5, 123.2, 105.2;
HREIMS: calcd for C13H8O335Cl2 (M+), 281.9850; found: 281.9851;
calcd for C13H8O337Cl2 (M+), 285.9791; found: 285.9816.
control ꢀ treated
Inhibitory rate ð%Þ ¼
ꢁ 100%
control
Acknowledgements
This work was supported by the National Key Project for Basic
Research (2010CB126101), the Shanghai Foundation of Science
and Technology (073919107) and the Open Funding Project of
the State Key Laboratory of Bioreactor Engineering.
3.2.10. (2E)-1-(3-Hydroxyfuran-2-yl)-3-(3-nitrophenyl)prop-2-
en-1-one (10)
Yield: 73%. Pale yellow solid, mp 186–188 °C; IR (KBr) mmax
:
2816, 2021, 1849, 1552, 1376, 1187, 768 cmꢀ1 1H NMR
;
(400 MHz, CDCl3): d 8.48 (s, 1H), 8.23 (d, J 8.0 Hz, 1H), 8.13 (d, J
7.6 Hz, 1H), 7.71–7.82 (m, 4H), 6.41 (s, 1H); 13C NMR (100 MHz,
CDCl3): d 174.6, 155.1, 149.0, 148.8, 138.6, 137.3, 137.1, 134.5,
131.0, 126.2, 124.7, 122.8, 106.8; HREIMS: calcd for C13H9NO5
(M+), 259.0481; found: 259.0482.
Supplementary data
Supplementary data (1H NMR spectra for compounds 1–12)
associated with this article can be found, in the online version, at
doi:10.1016/j.carres.2010.05.017.
3.2.11. (2E)-1-(3-Hydroxyfuran-2-yl)-3-(naphthalen-2-yl)prop-
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