Study on the structure-activity relations of brominated hydroxy diphenyl ethers derivatives with anilines

Article abstract of DOI:10.14233/ajchem.2013.13823

In order to study the influence of anilines on antibacterial activity, eight novel brominated hydroxy diphenyl ethers derivatives were designed and synthesized. The antibacterial activities of the new compounds were tested via agar-well diffusion method in vitro under different concentrations. The results showed the derivatives had antibacterial activities at the concentration 50 μg/mL against Staphylococcus aureus SC and Staphylococcus aureus ATCC26112.

Full text of DOI:10.14233/ajchem.2013.13823

Asian Journal of Chemistry; Vol. 25, No. 7 (2013), 3863-3866
http://dx.doi.org/10.14233/ajchem.2013.13823
Study on the Structure-Activity Relations of Brominated
Hydroxy Diphenyl Ethers Derivatives with Anilines
1
2
1
1,*
1
BIN LUO , HUA-HONG ZHOU , KANG-KANG YU , KAI-QUN WU , TIAN CHEN2,** and YU-LIANG WANG
1Faculty of Chemistry, Sichuan University, Chengdu 610065, P.R. China
2Department of Pathogenic Biology, School of Biomedical Science, Chengdu Medical College, Chengdu 610083, P.R. China
*Corresponding author: Tel: +86 13708058490, E-mail: wukaiqun@tom.com; luobinhxscu@126.com
**Corresponding author (For biological activities assay): Tel: +86 13540047681, E-mail: tianchen66@gmail.com
(Received: 3 April 2012;
Accepted: 14 January 2013)
AJC-12712
In order to study the influence of anilines on antibacterial activity, eight novel brominated hydroxy diphenyl ethers derivatives were
designed and synthesized. The antibacterial activities of the new compounds were tested via agar-well diffusion method in vitro under
different concentrations. The results showed the derivatives had antibacterial activities at the concentration 50 µg/mL against Staphylococcus
aureus SC and Staphylococcus aureus ATCC26112.
Key Words: Brominated hydroxy diphenyl ethers, Structure-activity, Anilines, Antibacterial activity.
tested via the agar-well diffusion method in vitro. The results
showed that target compounds had some antibacterial activities
against Staphylococcus aureus SC, Staphylococcus aureus
ATCC26112. The synthetic route is shown in Scheme-I.
INTRODUCTION
Brominated 2-hydroxy diphenyl ethers was first isolated
from the marine sponge Dysidea herbacea by Sharma et al.1
(Fig. 1, 1) and it was reported that brominated 2-hydroxy
diphenyl ethers could inhibit gram positive bacteria and gram
negative bacteria1,2. Afterwards, many literatures have focued
on the isolation and synthesise new brominated hydroxy diphenyl
ethers and their antibacterial activities3-5. These studies showed
that the hydroxy was necessary for keeping antibacterial
activity6,7 and fluorine as well as nitro substituent were favou-
rable for enhancing antibacterial activity8,9. They also emplyed
that some synthetic derivatives had a special antibacterial
activities such as a series of brominated dihydroxy diphenyl
ethers derivatives have been designed and synthesized with
good antibacterial activities10,11 (Fig. 1, 2). However, dioxins
were found during the separation of natural brominated 2-
hydroxy diphenyl ethers12,13 (Fig. 1, 3). In order to avoid the
generation of dioxins a series of brominated 3-hydroxy (Fig.
1, 4) and 4-hydroxy (Fig. 1, 5) diphenyl ethers derivatives
were designed and synthesized. The results showed that bromi-
nated 3-hydroxy and 4-hydroxy diphenyl ethers derivatives
had also a good antibacterial activities and will never form
dioxins14,15
.
In order to avoid the generation of dioxins and to study
the influence of anilines on antibacterial activity systematically,
a series of novel brominated 4-hydroxy diphenyl ethers deri-
vatives containing aniline have been designed and synthesized.
The antibacterial activities of the target compounds have been
Fig. 1. Brominated hydroxy diphenyl ethers and related derivatives

3864 Luo et al.
Asian J. Chem.
General preparation procedure of 6a-g: A mixture of
5a-g (1 mmol) and 40 % HBr (6 mmol) in acetic acid (20 mL)
was refluxed at 125 ºC for 9~11 h, cooled, the pH was adjusted
to 7 with saturated NaHCO3 solution and the mixture was
extracted with ethyl acetate. The organic layer was filtered,
dried and evaporated in vacuo to give the crude product. The
crude product was chromatographed on silica gel using petro-
leum ether/ethyl acetate (4:1) as eluent to afford a pure product
(yield 45-85 %).
General preparation procedure of 7a-h: 6a-g (1 mmol)
was dissolved in ethyl acetate/dichloromethane (1:1, 20 mL)
and the mixture was heated to reflux. Liquid bromide (6 mmol
) was dissolved in ethyl acetate/dichloromethane (1:1, 4 mL)
and the solution was added dropwise. The reaction mixture
was refluxed for 7 h, cooled, the reaction mixture was washed
by 5 % Na2S2O3, saturated NaHCO3 solution, water. The organic
layer was filtered, dried and evaporated in vacuo to give the
crude product. The crude product was chromatographed on
silica gel using petroleum ether/ethyl acetate (20:1) as eluent
to afford a pure product (yield 45-55 %).
5a, 5c are known compounds reported in literature17 and
were identified by melting point test, 1H NMR and IR, all data
was the same with the literature.
3-Chloro-4-(4-methoxyphenoxy)-N,N-dimethyl-
benzen-amine (5b): Yellow solid; yield:52.3 %, m.p.: 52-54
ºC; 1H NMR spectrum (400 MHz; d1-CDCl3; TMS): δ (ppm)
= 2.93 (6H, s), 3.77 (3H, s), 6.58 (1H, dd, J1= 8.8 Hz, J2= 2.8
Hz), 6.77 (1H, d, J= 2.8 Hz), 6.81-7.03 (5H, m); IR (KBr,
Scheme-I: Synthetic route of compounds 7a-7h
EXPERIMENTAL
Melting points were recorded on an XRC-1 melting point
apparatus (Sichuan University Instrument Inc., Chengdu,
China) without being corrected. 1H NMR spectra were run on
aVarian INOVA-400 spectrometer (Varian Inc., PaloAlto, CA,
USA) with CDCl3 as the solvent and TMS as the internal
standard. Mass spectra were recorded with an Agilent 6210
(DOF-MAS) spectrometer (Agilent Inc., Santa Clara, CA,
USA) using the electrospray ionization (ESI) method. IR spectra
were recorded with a Perkin-Elmer 16PC-FT instrument
(Perkin-Elmer Inc., Norwalk Conn, CA, USA). Compounds 1
and 2 were commercially available, compounds 3 and 4 were
synthesized according to the literature16.
ν
1202, 1039, 961, 879, 828, 772.
max, cm-1) 3040, 2936, 2834, 1607, 1562, 1499, 1443, 1234,
3-Chloro-4-(4-methoxyphenoxy)-N,N-diethyl-
benzenamine (5d): Yellow oilyliquid; yield: 80.2 %;1H NMR
spectrum (400 MHz; d1-CDCl3; TMS): δ (ppm) = 0.93 (6H, t,
J = 7.6 Hz), 3.19 (4H, q, J = 7.6 Hz), 3.77 (3H, s), 6.53 (1H, dd,
J1 = 8.8 Hz, J2 = 2.8 Hz), 6.66 (1H, d, J = 2.8 Hz), 6.81-7.00
(5H, m); IR (KBr, νmax, cm-1) 3046, 2970, 2835, 1607, 1556,
1498, 1376, 1356, 1232, 1200, 1039, 874, 826, 794, 756.
4-(4-Methoxyphenoxy)-N,N-dipropylbenzenamine
(5e):Yellow oilyliquid; yield: 65.3 %; 1H NMR spectrum (400
MHz; d1-CDCl3; TMS): δ (ppm) = 0.92 (6H, t, J = 7.6 Hz),
1.59 (4H, m), 3.19 (4H, t, J = 7.6 Hz), 3.83 (3H, s), 6.60 (2H, d,
J = 8.8 Hz); 6.81-6.92 (6H, m); IR (KBr, νmax, cm-1): 3045,
2960, 2873, 2835, 1612, 1500, 1462, 1370, 1225, 1100, 1037,
873, 824,746.
General preparation procedure of 5a-b: A mixture of
4 (1 mmol) and NaOH (5 mmol) in solvent (20 mL, dry
ethanol:water = 3:1) was stirred at 0-5 ºC, then dimethyl sulfate
(6 mmol) was added dropwise. Reaction solution was stirred
at 0-15 ºC for 24 h. Then the pH was adjusted to 7 with diluted
hydrochloric acid, 20 mL water was added and the mixture
was extracted with ethyl acetate. The organic layer was filtered,
dried and evaporated in vacuo to give the crude product. The
crude product was chromatographed on silica gel using petro-
leum ether/ethyl acetate (16:1) as eluent to afford a pure product
(yield 50-55 %).
4-(4-Methoxyphenoxy)-N,N-dibutyl-benzenamine (5f):
1
Yellow oily liquid; yield: 60.3 %; H NMR spectrum (400
MHz; d1-CDCl3; TMS): δ (ppm) = 0.95 (6H, t, J = 7.2 Hz),
1.34 (4H, m), 1.50 (4H, m), 3.22 (4H, t, J = 7.6 Hz), 3.80 (3H,
s), 6.60 (2H, d, J = 8.8 Hz), 6.81-6.90 (6H, m); IR (KBr, νmax
,
cm-1): 3044, 2957, 2868, 1611, 1500, 1462, 1369, 1277, 1227,
1105, 1037, 824.
General preparation procedure of 5c-g: A mixture of
4 (1 mmol), dry Na2CO3 (3 mmol) and RBr (3-6 mmol) in dry
DMF (20 mL) was stirred at 60~110 ºC for 3~24 h, cooled.
20 mL water was added and the mixture was extracted with
ethyl acetate. The organic layer was filtered, dried and evapo-
rated in vacuo to give the crude product. The crude product
was chromatographed on silica gel using petroleum ether/ethyl
acetate (16:1) as eluent to afford a pure product (yield 60-
92 %).
3-Chloro-4-(4-methoxyphenoxy)-N,N-dibenzyl-
benzenamine (5g): Colourless oilyliquid; yield: 91.3 %; 1H
NMR spectrum (400 MHz; d1-CDCl3; TMS): δ (ppm) = 3.77
(3H, s), 4.67 (4H, s), 6.56 (1H, dd, J1 = 8.8 Hz, J2 = 3.2 Hz),
6.79-6.91 (6H, m), 7.07-7.39 (10H, m); IR (KBr, νmax, cm-1):
3029, 2946, 2833, 1604, 1497, 1452, 1393, 1361, 1230, 1200,
1030, 957, 883, 821, 733, 696.

Vol. 25, No. 7 (2013) Study on the Structure-Activity Relations of Brominated Hydroxy Diphenyl Ethers Derivatives with Anilines 3865
4-[4-(Dimethylamino)phenoxy]phenol (6a): White
1
solid; yield: 84.7 %, m.p.: 133-135 ºC; H NMR spectrum
2,6-Dibromo-4-[3-bromo-5-chloro-4-(dimethylamino)-
phenoxy]phenol (7b): White solid; yield: 47.7 %, m.p.: 109-
1
111 ºC; H NMR spectrum (400 MHz; d1-CDCl3; TMS): δ
(400 MHz; d1-CDCl3; TMS): δ (ppm) = 2.93 (6H, s), 4.61
(1H, s), 6.76 (2H, d, J = 8.4 Hz), 6.85 (4H, d, J = 8.8 Hz), 6.92
(2H, d, J = 8.8 Hz); IR (KBr, νmax, cm-1): 3430, 3043, 2895,
2813, 1603, 1502, 1451, 1366, 1303, 1227, 1145, 1096, 1051,
932, 871, 826.
(ppm) = 2.80 (6H, s), 5.68 (1H, s), 7.08 (1H, s), 7.15 (1H, s),
7.20 (1H, s), 7.30 (1H, s); IR (KBr, νmax, cm-1): 3284, 3081,
2960, 2873, 2841, 2797, 1593, 1564, 1464, 1400, 1355, 1317,
1216, 1184, 1134, 1072, 1045, 970, 932, 887, 852, 801, 768,
733, 681, 580, 517, 466, 422; HR-MS (ESI): Calcd. for
C14H12NO2Br3Cl [M+H]+: 497.8107, 499.8087, 501.8067;
Found: 497.8091,499.8069, 501.8048.
4-[2-Chloro-4-(dimethylamino)phenoxy]phenol (6b):
White solid; yield: 83.6 %, m.p.: 127-129 ºC; 1H NMR spec-
trum (400 MHz; d1-CDCl3; TMS): δ (ppm) = 2.94 (6H, s),
4.53 (1H, s), 6.61-6.83 (5H, m), 6.91 (2H, d, J = 8.8 Hz); IR
(KBr, νmax, cm-1) 3097, 2921, 2821, 1600, 1495, 1443, 1355,
1237, 1142, 1052, 948, 879, 822, 782, 509.
2,6-Dibromo-4-[4-(diethylamino)phenoxy]phenol (7c):
White solid; yield: 48.9 %, m.p.: 103-105 ºC; 1H NMR spec-
trum (400 MHz; d1-CDCl3; TMS): δ (ppm) = 1.17 (6H, t, J =
6.8 Hz), 3.34 (4H, q, J = 6.8 Hz), 5.58 (1H, s), 6.66 (2H, d, J
4-[4-(Diethylamino)phenoxy]phenol (6c): White solid;
yield: 82.0 %, m.p.: 113-115 ºC; 1H NMR spectrum (400 MHz;
d1-CDCl3; TMS): δ (ppm) = 1.16 (6H, t, J = 3.6 Hz), 3.31 (4H,
q, J = 6.8Hz), 4.87 (1H, s), 6.76 (2H, d, J = 8.8 Hz), 6.86 (4H,
d, J = 8.8 Hz), 6.89 (2H, d, J = 9.2 Hz); IR (KBr, νmax, cm-1):
3385, 3041, 2972, 2931, 1607, 1500, 1448, 1354, 1224, 1094,
1010, 872, 820.
= 8.8 Hz), 6.88 (2H, d, J = 9.2 Hz), 7.08 (2H, s); IR (KBr, νmax
,
cm-1): 3501, 3076, 2970, 2928, 1606, 1510, 1465, 1402, 1320,
1263, 1218, 1150, 1011, 934, 820, 792, 742, 576; HR-MS
(ESI): Calcd. for C16H18NO2Br2 [M+H]+: 413.9705, 415.9685,
417.9664; Found: 413.9698, 415.9706, 417.9661.
2,6-Dibromo-4-[2-chloro-4-(diethylamino)phenoxy]-
phenol (7d): Yellow solid; yield: 54.3 %; m.p.: 106-108 ºC;
1H NMR spectrum (400 MHz; d1-CDCl3; TMS): δ (ppm) =
1.18 (6H, t, J = 7.2 Hz), 3.33 (4H, q, J = 7.2 Hz), 5.57 (1H, s),
6.53 (1H, d, J = 8.8 Hz), 6.68 (1H, d, J = 2.4 Hz), 6.91 (1H, d,
J = 8.8 Hz), 7.02 (2H, s); IR (KBr, νmax, cm-1): 3517, 3073,
2969, 2927, 1607, 1562, 1503, 1466, 1403, 1356, 1318, 1276,
1233, 1196, 1150, 1071, 1042, 1016, 930, 800, 752, 695, 580,
436; HR-MS (ESI): Calcd. for C16H17NO2Br2Cl [M+H]+:
447.9315, 449.9295, 451.9274; Found: 447.9305, 449.9284,
451.9267.
4-[2-Chloro-4-(diethylamino)phenoxy]phenol (6d):
Yellow oilyliquid; yield: 79.5 %; 1H NMR spectrum (400 MHz;
d1-CDCl3; TMS): δ (ppm) = 1.16 (6H, t, J = 7.2 Hz), 3.32 (4H,
q, J = 7.2Hz), 4.58 (1H, s), 6.53 (1H, dd, J1 = 8.8 Hz, J2 = 2.8
Hz), 6.70 (1H, d, J = 2.8 Hz), 6.75 (1H, d, J = 9.2 Hz), 6.80
(2H, d, J = 8.8 Hz), 6.89 (2H, d, J = 8.8 Hz); IR (KBr, νmax
,
cm-1): 3390, 3033, 2972, 2931, 1605, 1557, 1505, 1356, 1233,
1096, 1045, 1013, 924, 874, 828, 768, 693, 607, 512.
4-[4-(Dipropylamino)phenoxy]phenol (6e): Yellow
1
oilyliquid; yield: 73.8 %; H NMR spectrum (400 MHz; d1-
CDCl3; TMS): δ (ppm) = 0.92 (6H, t, J = 7.6 Hz), 1.59 (4H,
m), 3.19 (4H, t, J = 7.6 Hz), 4.60 (1H, s), 6.60 (2H, d, J = 8.8
Hz); 6.75 (2H, d, J = 8.8 Hz), 6.84-6.87 (4H, m); IR (KBr,
2,6-Dibromo-4-[4-(dipropylamino)phenoxy]phenol
1
(7e): Yellow oilyliquid; yield: 48.7 %; H NMR spectrum
(400 MHz; d1-CDCl3; TMS): δ (ppm) = 0.93 (6H, t, J = 7.2
Hz), 1.63 (4H, m, J = 7.6 Hz), 3.22 (4H, t, J = 7.6 Hz), 5.55
(1H, s), 6.60 (2H, d, J = 9.2 Hz), 6.86 (2H, d, J = 9.2 Hz),
7.07 (2H, s); IR (KBr, νmax, cm-1): 3505, 3077, 2960, 2872,
1607, 1565, 1510, 1465, 1402, 1321, 1218, 1150, 1101, 1047,
932, 819, 744, 549; HR-MS (ESI): Calcd. for C18H22NO2Br2
[M+H]+: 442.0018, 443.9998, 445.9977; Found: 442.0013,
443.9999, 445.9976.
ν
1364, 1222, 1098, 1046, 873, 818,757.
4-[4-(Dibutylamino)phenoxy]phenol (6f): Yellow
max, cm-1): 3404, 3046, 2962, 2931, 2873, 1608, 1500, 1460,
1
oilyliquid; yield: 70.1 %; H NMR spectrum (400 MHz; d1-
CDCl3; TMS): δ (ppm) = 0.95 (6H, t, J = 7.2 Hz), 1.34 (4H,
m), 1.50 (4H, m), 3.22 (4H, t, J = 7.6 Hz), 6.61 (2H, d, J = 8.4
Hz), 6.75 (2H, d, J = 8.8 Hz), 6.85-6.89 (4H, m); IR (KBr,
ν
1227, 1105, 1037, 824.
max, cm-1): 3044, 2957, 2868, 1611, 1500, 1462, 1369, 1277,
2,6-Dibromo-4-[4-(dibutylamino)phenoxy]phenol (7f):
Yellow oilyliquid; yield: 40.2 %; 1H NMR spectrum (400 MHz;
d1-CDCl3; TMS): δ (ppm) = 0.96 (6H, t, J = 7.6 Hz), 1.36 (4H,
m), 1.57 (4H, m), 3.24 (4H, t, J = 7.6 Hz), 5.56 (1H, s), 6.60
(2H, d, J = 8.8 Hz), 6.86 (2H, d, J = 8.8 Hz), 7.08 (2H, s); IR
(KBr, νmax, cm-1): 3511, 3078, 3044, 2956, 2866, 1608, 1565,
1510, 1465, 1402, 1369, 1321, 1215, 1149, 1109, 1051, 1008,
931, 818, 782, 744, 697, 578; HR-MS (ESI): Calcd. for
C20H26NO2Br2 [M+H]+: 470.0331, 472.0311, 474.0290; Found:
470.0334, 472.0306, 474.0297.
4-[2-Chloro-4-(dibenzylamino)phenoxy]phenol (6g):
Colourless oilyliquid; yield: 45.3 %; 1H NMR spectrum (400
MHz; d1-CDCl3; TMS): δ (ppm) = 4.30 (4H, s), 4.60 (1H, s),
6.63 (1H, d, J = 8.8 Hz ), 6.76 (1H, d, J = 3.2 Hz), 6.88-7.01
(5H, m), 7.28-7.39 (10H, m); IR (KBr, νmax, cm-1): 3335, 3030,
2874, 1604, 1504, 1449, 1357, 1250, 1095, 1053, 1006, 959,
884, 836, 801, 737, 698, 405.
2,6-Dibromo-4-[4-(dimethylamino)phenoxy]phenol
(7a): Yellow solid; yield:15.3%; m.p.: 126-128 ºC; 1H NMR
spectrum (400 MHz; d1-CDCl3; TMS): δ (ppm) = 2.78 (6H,
s), 5.36 (1H, s), 6.88 (2H, d, J = 2.8 Hz), 7.01 (2H, d, J = 5.6
Hz), 7.16 (2H, s); IR (KBr, νmax, cm-1) 3503, 3069, 2929, 2866,
2784, 1592, 1498, 1415, 1324, 1267, 1212, 1185, 1034, 916,
883, 817, 781, 569; HR-MS (ESI): Calcd. for C14H14NO2Br2
[M+H]+: 385.9392, 387.9372, 389.9351; Found: 385.9381,
387.9363, 389.9345.
2,6-Dibromo-4-[5-bromo-2-chloro-4-(dibenzylamino)-
phenoxy]phenol (7g): White solid; yield: 49.9 %, m.p.: 180-
1
182 ºC; H NMR spectrum (400 MHz; d1-CDCl3; TMS): δ
(ppm) = 4.67 (4H, s), 5.64 (1H, s), 7.02 (1H, s), 7.08 (3H, d, J
= 6.8 Hz), 7.15-7.29 (10H, m); IR (KBr, νmax, cm-1): 3476,
3381, 3074, 2923, 2853, 1605, 1568, 1451, 1409, 1383, 1309,
1278, 1218, 1189, 1155, 1067, 973, 922, 848, 779, 737, 713,
582, 532, 493, 454; HR-MS (ESI): Calcd. for C26H20NO2Br2Cl

3866 Luo et al.
Asian J. Chem.
[M+H]+: 649.8733, 651.8713, 653.8693; Found: 649.8718,
651.8699, 653.8683.
During the preparation of 5a-g, by-products increased as
the reduction of activities of RBr. So it's necessary to increase
reaction temperature and time. Otherwise, RBr were vapourized
along with long-playing heating, so more RBr needed during
reaction process.
2,6-Dibromo-4-[2-bromo-4-(dimethylamino)phenoxy]-
phenol (7h): White solid; yield: 45.4 %, m.p.: 120-122 ºC; 1H
NMR spectrum (400 MHz; d1-CDCl3; TMS): δ (ppm) = 2.78
(6H, s), 5.70 (1H, s), 6.90 (1H, dd, J1 = 8.8 Hz, J2 = 2.8 Hz),
7.08 (1H, d, J = 8.8 Hz), 7.14 (1H, s), 7.2 (2H, d, J = 2.8 Hz);
IR (KBr, νmax, cm-1): 3418, 3078, 2954, 1586, 1559, 1464,
1403, 1338, 1263, 1213, 1153, 1034, 937, 864, 789, 752,
669,584, 544; HR-MS (ESI): Calcd. for C14H13NO2Br3 [M+H]+:
463.8497, 465.8477, 466.8456; Found: 463.8488, 465.8466,
466.8443.
As shown in Scheme-I, the intermediates 6a-g were
synthesized by 5a-g with HBr in HAc. On this condition the
benzyl located in the nitrogen would fall off partially, so the
yield of the intermediate 6g was very low.
Conclusion
In conclusion, eight novel brominated hydroxy diphenyl
ethers derivatives were designed and synthesized. Compared
to 4-hydroxy (Fig. 1, 5) diphenyl ethers derivatives15 with
nitro group which exhibited good antibacterial activity at the
concentration of 10 µg/mL, all target compounds have similar
structures with them, but their antibacterial activities are much
worse. This made a further proof that nitro group is important
for enhancing antibacterial activitiy. We will continue to study
structure-activity relations of brominated hydroxy diphenyl
ethers derivatives.
Biological assay: Wild Staphylcoccus aures SC and standard
Staphylcoccus aures ATCC26112 were used in the studies.
The antibacterial activities of the target compounds in vitro
were tested via agar-well diffusion method. Every sample
(1000 µg) was dissolved with ethanol (1 mL) and diluted to
50 µg/mL with ethanol. The resulting solution was added to
the flat plate of an Oxford cup which was covered with culture
and kept at 37 ºC for 24 h. The results of average diameters of
the bacteriostatic circle are listed in Table-1.
ACKNOWLEDGEMENTS
RESULTS AND DISCUSSION
The authors appreciated the financial support from the
National Science Foundation of China (No. 21072135), the
antibacterial activity test of Chengdu Medical College
(cx20100037) and the 1H NMR analysis by Sichuan University
Analytical & Testing Center.
The bioactivities of compounds 7a-h against S. aureus
ATCC26112 and S. aureus SC are shown in Table-1. The results
showed that all target compounds exhibited antibacterial
activity at the concentration of 50.0 µg/mL.
REFERENCES
1. G.M. Sharma, B. Vig and P.R. Burkholder, Marine Technology Society,
Washington D.C. (1969).
TABLE-1
ANTIBACTERIAL ACTIVITY OF THE TARGET COMPOUNDS
(7a-h) AT THE CONCENTRATION OF 50.0 µg/mL TOWARD
S. aureus ATCC26112 and S. aureus SC
2. G.M. Sharma and B. Vig, Tetrahedron Lett., 13, 1715 (1972).
3. B. Carté and D.J. Faulkner, Tetrahedron, 37, 2335 (1981).
4. R.S. Norton, K.D. Croft and R.J. Wells, Tetrahedron, 37, 2341 (1981).
5. E.N. Segraves, R.R. Shah, N.L. Segraves, T.A. Johnson, S. Whitman,
J.K. Sui, V.A. Kenyon, R.H. Cichewicz, P. Crews and T.R. Holman, J.
Med. Chem., 47, 4060 (2004).
Diameter of inhibition zone (mm)
Compound
S. aureus ATCC26112
S. aureus SC
11
13
7a
7b
7c
7d
7e
7f
6. J. Salvá and D.J. Faulkner, J. Nat. Prod., 53, 757 (1990).
7. D. Handayani, R.A. Edrada, P. Proksch, V. Wray, L. Witte, R.W.M.
Van Soest and A. Kunzmann, J. Nat. Prod., 60, 1313 (1997).
8. Y.L. Wang, M.L. Ma and S.H. Chen, Youji Huaxue, 25, 734 (2005).
9. K.Q. Wu, Y.L. Wang and H. Zheng, CN 1597657 (2005).
10. H. Jin, S. Chen and R.T. Hou, Youji Huaxue, 26, 1424 (2006).
11. S. Chen, Y. Xin and Y. Zhan, Youji Huaxue, 3, 498 (2008).
12. N.K. Utkina, V,A. Denisenko, O.V. Scholokova, M.V. Virovaya, A.V.
Gerasimenko, D.Y. Popov, V.B. Krasokhin and A.M. Popov, J. Nat.
Prod., 64, 151 (2001).
9
8
10
8
11.5
13
7
11
12
9
7
9
7g
7h
13. N.K. Utkina, V.A. Denisenko, M,V. Virovaya, O,V. Scholokova and
N.G. Prokof'eva, J. Nat. Prod., 65, 1213 (2002).
8.5
10
14. X. Tang, M. Xie, Y.X. Sun, J.H. Liu, Z.C. Zhong and Y.L. Wang, Chin.
Chem. Lett., 20, 435 (2009).
Triclosan
Ethanolb
22
-
20
-
15. Y. Zou, J. Wu and R.T. Hou, Youji Huaxue, 1, 111( 2008).
16. Z.X. Yang, H. Chen and Y.L. Wang, Youji Huaxue, 3, 432 (2008).
17. T. Saitoh and J. Ichikawa, J. Am. Chem. Soc., 127, 9696 (2005).
a: Concentration of triclosan: 20.0 µg/mL; as the positive control;
b: negative control: ethanol; diameter of the well in each plate: 6 mm