ACS Combinatorial Science
ARTICLE
8.18 (1H, s, -N=CH), 8.09 (2H, d, J = 7.6 Hz, ArH), 8.04 (1H, s, ArH),
7.60 (2H, d, J = 8.0 Hz, ArH), 7.55-7.47 (3H, m, ArH), 7.31 (1H,
s, =CH), 7.24-7.20 (2H, m, ArH), 6.99 (1H, d, J = 8.4 Hz, ArH), 3.76
(3H, s, -OCH3), 3.55 (3H, s, -OCH3). 13C NMR (100 MHz, DMSO-
d6): 165.9, 164.3, 149.4, 148.3, 146.4, 137.0, 133.6, 133.4, 132.2, 131.7,
129.3, 128.7, 128.3, 127.9, 126.9 123.5, 122.7, 121.5, 112.5, 111.6, 111.0,
109.8, 55.6, 55.1. HRMS (ESI): m/z calcd for C25H23N4O4: 443.1714
[MþH]þ; found: 443.1731 [MþH]þ.
for another 24 h. The fresh 1640 medium containing no tested
compounds was used as the blank control. An aliquot of 20 μL of
MTT tetrazolium salt dissolved in Hank's balanced salt solution at a final
concentration of 5 mg/mL was added to each well and incubated in the
CO2 incubator for 4 h. Finally, the medium was aspirated from each well
and 150 μL of DMSO was added to dissolve the formazan crystals. The
absorbance of each well was obtained using a Dynatech MR5000 plate
counter at a wavelength of 570 nm. The inhibition rate was calculated
according to the following formula: Inhibition rate = (OD570 blank control
- OD570 tested compounds) /OD570 blank control ꢀ 100%, where OD stands
for optical density at 570 nm.
N-(1-(2-methylbenzo[d]thiazol-5-ylcarbamoyl)-2-p-tolylvinyl)-
benzamide (3{6,2}). Pale yellow solid, mp: 255-258 °C. IR (KBr,
ν, cm-1): 3230, 3067, 1646, 1576, 1520, 1466, 1323, 1294, 1256,
1183, 804, 696. 1H NMR (400 MHz, DMSO-d6): 10.38 (1H, s, NH),
10.13 (1H, s, NH), 8.39 (1H, s, ArH), 8.04 (2H, d, J = 7.6 Hz, ArH),
7.95 (1H, d, J = 8.4 Hz, ArH), 7.73 (1H, d, J = 8.4 Hz, ArH),
7.62-7.51 (5H, m, ArH), 7.21 (2H, d, J = 7.6 Hz, ArH), 7.17 (1H, s,
=CH), 2.79 (3H, s, -CH3), 2.31 (3H, s, -CH3). 13C NMR (100
MHz, DMSO-d6): 167.7, 164.6. 153.4, 138.4, 137.8, 136.4, 133.6,
133.5, 133.1, 131.7, 131.4, 130.1, 129.6, 129.5, 129.1, 128.7, 128.3,
127.9, 121.5, 118.1, 112.9, 112.7, 20.9, 19.8. HRMS (ESI): m/z calcd
for C25H22N3O2S: 428.1428 [MþH]þ; found: 428.1442 [MþH]þ.
N-(1-(9H-fluoren-7-ylcarbamoyl)-2-(4-nitrophenyl)vinyl)benzamide
(3{3,3}). Yellow solid, mp: 285-287 °C. IR (KBr, ν, cm-1): 3257,
3107, 2944, 1637, 1616, 1547, 1519, 1466, 1343, 1317, 1256, 865, 802,
’ ASSOCIATED CONTENT
S
Supporting Information. Experimental procedures, char-
b
acterization data, and 1H and 13C NMR spectra of compounds 3.
This material is available free of charge via the Internet at http://
pubs.acs.org.
’ AUTHOR INFORMATION
Corresponding Author
*Phone: 0086-516-83500065. Fax: 0086-516-83500065. E-mail:
1
768, 736, 712. H NMR (400 MHz, DMSO-d6): 10.47 (1H, s, NH),
10.34 (1H, s, NH), 8.27 (2H, d, J = 8.8 Hz, ArH), 8.07 (1H, s, ArH), 8.03
(2H, d, J = 7.6 Hz, ArH), 7.89 (2H, d, J = 8.8 Hz, ArH), 7.85 (2H, t, J =
7.6 Hz, ArH), 7.73 (1H, d, J = 7.6 Hz, ArH), 7.65-7.52 (4H, m, ArH),
7.37 (1H, t, J = 7.6 Hz, ArH), 7.28 (1H, t, J = 7.6 Hz, ArH), 7.18 (1H, s,
=CH), 3.93 (2H, s, -CH2). 13C NMR (100 MHz, DMSO-d6): 166.0,
163.9, 146.5, 143.6, 142.9, 141.6, 141.0, 138.2, 136.6, 134.6, 133.2, 132.0,
130.3, 128.4, 128.0, 126.7, 126.2, 125.0, 124.5, 123.7, 120.0, 119.5, 118.8,
116.7, 36.5. HRMS (ESI): m/z calcd for C29H22N3O4: 476.1605
[MþH]þ; found: 476.1606 [MþH]þ.
Funding Sources
We are grateful for the financial support from the Natural Science
Foundation of China (No. 21002083 and 21072163), the Natural
Science Foundation (09KJB150011) and Qing Lan Project
(08QL001) of Jiangsu Education Committee, and the Interdis-
ciplinary Key Item of Xuzhou Normal University (09XKXK01).
N-(1-(methylcarbamoyl)-2-(2,4-dichlorophenyl)vinyl)benzamide
(3{12,4}). Pale yellow solid, mp: 218-219 °C. IR (KBr, ν, cm-1):
’ REFERENCES
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3313, 3238, 3067, 1637, 1551, 1483, 1279, 868, 788, 693. H NMR
(400 MHz, DMSO-d6): 9.91 (1H, s, NH), 8.24 (1H, d, J = 4.4 Hz, NH),
7.91 (2H, d, J = 7.6 Hz, ArH), 7.70 (1H, s, ArH), 7.57-7.47 (4H, m,
ArH), 7.37 (1H, d, J = 8.4 Hz, ArH), 7.16 (1H, s, =CH), 2.70 (3H, d,
J = 4.4 Hz, -CH3). 13C NMR (100 MHz, DMSO-d6): 164.8, 134.0,
133.5, 133.3, 132.1, 131.7, 130.8, 130.6, 128.9, 128.2, 127.8, 127.3, 112.7,
26.3. HRMS (ESI): m/z calcd for C17H14Cl2N2O2Na: 371.0325
[MþNa]þ; found: 371.0326 [MþNa]þ.
N-(1-(cyclopropylcarbamoyl)-2-(4-chlorophenyl)vinyl)benzamide
(3{2,5}). White solid, mp: 211-212 °C. IR (KBr, ν, cm-1): 3231,
2998, 1669, 1644, 1524, 1486, 1311, 887, 810, 714. 1H NMR (400 MHz,
DMSO-d6): 9.87 (1H, s, NH), 8.23 (1H, d, J = 4.0 Hz, NH), 7.97 (2H, d,
J = 7.6 Hz, ArH), 7.59-7.48 (5H, m, ArH), 7.41 (2H, d, J = 8.8 Hz,
ArH), 7.03 (1H, s, =CH), 2.78-2.73 (1H, m, -CH), 0.68-0.63 (2H,
m, -CH2), 0.54-0.51 (2H, m, -CH2). 13C NMR (100 MHz, DMSO-
d6): 166.3, 133.6, 133.4, 132.7, 131.6, 131.1, 130.8, 128.4, 128.3, 127.9,
126.4, 112.7, 23.0, 5.7. HRMS (ESI): m/z calcd for C19H17ClN2O2Na:
363.0871 [MþNa]þ; found: 363.0880 [MþNa]þ.
Cytotoxic Assay to Colon Carcinoma Cell Line SW1116.
SW1116 cell was maintained in RMPI 1640 (HyClone) with 10% fetal
bovine serum (FBS), 50 μg/mL streptomycin, and 50 μg/mL of
penicillin in a humidified atmosphere of 5% CO2 at 37 °C. The
cytotoxicity of the tested compounds 3 to SW1116 cells was assayed
using the MTT (methyl thiazolyl tetrazolium) method. Briefly, SW1116
cells were collected and seeded in 96-well plates at a density of 4.5 ꢀ
105 cells/mL. After incubation in a humidified atmosphere of 5% CO2 at
37 °C for 24 h, cells were exposed to fresh 1640 medium containing
tested compounds in the concentration of 10 μg/mL or three different
concentrations of 0.1, 1, and 10 μg/mL at 37 °C and allowed to culture
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dx.doi.org/10.1021/co1000458 |ACS Comb. Sci. 2011, 13, 147–153