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Two novel Schiff bases derived from indole and biphenyl have been designed and synthesized, namely 3-((
E)-{(
E)-[1-(biphenyl-4-yl)ethylidene]hydrazinylidene}methyl)-1-methyl-1
H-indole (
3-BEHMI) acetonitrile monosolvate, C
24H
21N
3·CH
3CN, and 3-((
E)-{(
E)-[1-(biphenyl-4-yl)ethylidene]hydrazinylidene}methyl)-1-methyl-1
H-indole (
3-BEHEI) acetonitrile monosolvate, C
24H
21N
3·CH
3CN. Their structures were characterized by elemental analysis, quadrupole time-of-flight MS, NMR and UV–Vis spectroscopy. The single-crystal packing structure of
3-BEHMI is largely dominated by C—H
π interactions and weak van der Waals interactions. The
in vitro cytotoxicity of the two title compounds have been evaluated against two tumour cell lines (A549 human lung cancer and 4T
1 mouse breast cancer) and two normal cell lines (MRC-5 normal lung cells and NIH 3T3 fibroblasts) by MTT assay. The results indicate that
3-BEHEI exhibits a slightly weaker antiproliferative capability (IC
50 = ∼50 µ
M) than the previously reported similar Schiff base
3-BEHI (IC
50 = ∼20 µ
M). This is in line with docking results.
3-BEHMI demonstrates a weak cytotoxic activity, with IC
50 values around 110 µ
M, which disagrees with its docking results. Overall, the tested compounds manifest relevant cytotoxicities on the selected cancer cell lines and normal cell lines. The UV–Vis and fluorescence spectra were recorded and reproduced through the TD-DFT method with four types of hybrid density functionals, including B3LYP, M062X, PBE1PBE and WB97XD.
Supporting information
CCDC reference: 1886316
Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: SHELXTL (Bruker, 2000) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).
3-((
E)-{(
E)-[1-(Biphenyl-4-yl)ethylidene]hydrazinylidene}methyl)-1-methyl-1
H-indole acetonitrile monosolvate
top
Crystal data top
C24H21N3·C2H3N | F(000) = 832 |
Mr = 392.49 | Dx = 1.184 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1280 (2) Å | Cell parameters from 380 reflections |
b = 8.2147 (1) Å | θ = 2.5–26.0° |
c = 32.9809 (6) Å | µ = 0.07 mm−1 |
β = 90.252 (2)° | T = 298 K |
V = 2202.08 (7) Å3 | Block, yellow |
Z = 4 | 0.30 × 0.27 × 0.20 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | 4300 independent reflections |
Radiation source: fine-focus sealed tube | 3623 reflections with I > 2σ(I) |
Detector resolution: 10.13 pixels mm-1 | Rint = 0.040 |
phi and ω scans | θmax = 26.1°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −9→10 |
Tmin = 0.971, Tmax = 0.993 | k = −10→9 |
26680 measured reflections | l = −34→40 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | Only H-atom displacement parameters refined |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.0717P)2 + 0.4656P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.151 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.16 e Å−3 |
4300 reflections | Δρmin = −0.16 e Å−3 |
344 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.021 (2) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F2, conventional R-factors R are based
on F, with F set to zero for negative F2. The threshold expression of
F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 1.0305 (2) | −0.0658 (2) | 0.16179 (5) | 0.0580 (4) | |
C2 | 1.1581 (2) | −0.0543 (2) | 0.13436 (6) | 0.0695 (5) | |
C3 | 1.2654 (3) | 0.0741 (3) | 0.13619 (6) | 0.0781 (6) | |
C4 | 1.2440 (3) | 0.1923 (3) | 0.16526 (6) | 0.0819 (6) | |
C5 | 1.1167 (2) | 0.1816 (2) | 0.19267 (6) | 0.0680 (5) | |
C6 | 1.00710 (19) | 0.05118 (18) | 0.19154 (4) | 0.0510 (4) | |
C7 | 0.86788 (18) | 0.04172 (17) | 0.22050 (4) | 0.0493 (3) | |
C8 | 0.87657 (19) | 0.1149 (2) | 0.25885 (5) | 0.0537 (4) | |
C9 | 0.74443 (19) | 0.1122 (2) | 0.28499 (5) | 0.0535 (4) | |
C10 | 0.59637 (18) | 0.03798 (17) | 0.27413 (4) | 0.0482 (3) | |
C11 | 0.5885 (2) | −0.0368 (2) | 0.23637 (5) | 0.0574 (4) | |
C12 | 0.7214 (2) | −0.0350 (2) | 0.21020 (5) | 0.0570 (4) | |
C13 | 0.45344 (18) | 0.04005 (18) | 0.30195 (4) | 0.0501 (3) | |
C14 | 0.2979 (2) | −0.0395 (3) | 0.28876 (6) | 0.0825 (6) | |
H14A | 0.3158 | −0.1543 | 0.2857 | 0.179 (16)* | |
H14B | 0.2629 | 0.0060 | 0.2633 | 0.115 (9)* | |
H14C | 0.2145 | −0.0214 | 0.3088 | 0.094 (7)* | |
C15 | 0.3693 (2) | 0.1851 (2) | 0.39525 (5) | 0.0636 (4) | |
C16 | 0.2504 (2) | 0.2018 (2) | 0.42686 (5) | 0.0616 (4) | |
C17 | 0.0815 (2) | 0.1469 (2) | 0.42844 (5) | 0.0599 (4) | |
C18 | −0.0230 (2) | 0.0630 (2) | 0.40208 (6) | 0.0686 (5) | |
C19 | −0.1814 (3) | 0.0321 (3) | 0.41404 (8) | 0.0835 (6) | |
C20 | −0.2386 (3) | 0.0810 (3) | 0.45228 (9) | 0.0940 (8) | |
C21 | −0.1384 (3) | 0.1627 (3) | 0.47869 (7) | 0.0852 (7) | |
C22 | 0.0210 (2) | 0.1956 (2) | 0.46654 (5) | 0.0682 (5) | |
C23 | 0.2810 (3) | 0.2782 (3) | 0.46332 (6) | 0.0735 (5) | |
C24 | 0.1338 (4) | 0.3442 (4) | 0.52775 (6) | 0.0999 (9) | |
H24A | 0.0406 | 0.4156 | 0.5292 | 0.122 (9)* | |
H24B | 0.2323 | 0.4040 | 0.5339 | 0.21 (2)* | |
H24C | 0.1211 | 0.2573 | 0.5469 | 0.140 (11)* | |
C25 | 0.2584 (5) | 0.7005 (5) | 0.39055 (10) | 0.1204 (10) | |
H25A | 0.2202 | 0.8091 | 0.3853 | 0.32 (3)* | |
H25B | 0.1659 | 0.6307 | 0.3956 | 0.21 (2)* | |
H25C | 0.3180 | 0.6611 | 0.3675 | 0.198 (19)* | |
C26 | 0.3626 (3) | 0.7014 (4) | 0.42481 (8) | 0.0950 (7) | |
N1 | 0.47564 (16) | 0.11150 (19) | 0.33626 (4) | 0.0608 (4) | |
N2 | 0.33775 (17) | 0.11183 (19) | 0.36187 (4) | 0.0608 (4) | |
N3 | 0.1452 (2) | 0.2767 (2) | 0.48697 (4) | 0.0763 (5) | |
N4 | 0.4440 (3) | 0.7039 (6) | 0.45186 (9) | 0.1703 (16) | |
H1 | 0.959 (2) | −0.153 (2) | 0.1602 (5) | 0.066 (5)* | |
H2 | 1.169 (2) | −0.140 (3) | 0.1140 (6) | 0.077 (6)* | |
H3 | 1.359 (3) | 0.077 (3) | 0.1186 (6) | 0.086 (6)* | |
H4 | 1.323 (3) | 0.283 (3) | 0.1675 (6) | 0.088 (6)* | |
H5 | 1.105 (3) | 0.266 (3) | 0.2116 (7) | 0.092 (7)* | |
H8 | 0.977 (2) | 0.176 (2) | 0.2677 (5) | 0.063 (5)* | |
H9 | 0.753 (2) | 0.159 (2) | 0.3112 (6) | 0.067 (5)* | |
H11 | 0.489 (2) | −0.082 (2) | 0.2283 (5) | 0.065 (5)* | |
H12 | 0.707 (2) | −0.081 (2) | 0.1825 (6) | 0.075 (6)* | |
H15 | 0.477 (3) | 0.236 (3) | 0.3994 (6) | 0.080 (6)* | |
H18 | 0.011 (2) | 0.029 (2) | 0.3748 (6) | 0.061 (5)* | |
H19 | −0.255 (3) | −0.020 (3) | 0.3967 (8) | 0.098 (8)* | |
H20 | −0.343 (3) | 0.055 (3) | 0.4605 (8) | 0.110 (8)* | |
H21 | −0.178 (3) | 0.200 (3) | 0.5051 (7) | 0.087 (6)* | |
H23 | 0.382 (3) | 0.330 (3) | 0.4728 (7) | 0.085 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0615 (9) | 0.0530 (8) | 0.0596 (9) | −0.0038 (7) | 0.0094 (7) | −0.0029 (7) |
C2 | 0.0754 (12) | 0.0713 (11) | 0.0619 (10) | −0.0031 (9) | 0.0181 (9) | −0.0093 (8) |
C3 | 0.0750 (12) | 0.0913 (14) | 0.0682 (11) | −0.0166 (10) | 0.0258 (9) | −0.0039 (10) |
C4 | 0.0851 (14) | 0.0897 (14) | 0.0711 (12) | −0.0353 (11) | 0.0204 (10) | −0.0111 (10) |
C5 | 0.0772 (12) | 0.0658 (10) | 0.0610 (10) | −0.0173 (9) | 0.0134 (8) | −0.0101 (8) |
C6 | 0.0539 (8) | 0.0511 (8) | 0.0482 (8) | 0.0003 (6) | 0.0034 (6) | 0.0025 (6) |
C7 | 0.0534 (8) | 0.0451 (7) | 0.0494 (8) | 0.0011 (6) | 0.0043 (6) | 0.0013 (6) |
C8 | 0.0489 (8) | 0.0601 (9) | 0.0521 (8) | −0.0023 (7) | 0.0017 (6) | −0.0053 (7) |
C9 | 0.0513 (8) | 0.0612 (9) | 0.0481 (8) | 0.0003 (7) | 0.0012 (6) | −0.0064 (7) |
C10 | 0.0494 (8) | 0.0467 (7) | 0.0485 (7) | 0.0017 (6) | 0.0025 (6) | 0.0025 (6) |
C11 | 0.0564 (9) | 0.0603 (9) | 0.0556 (9) | −0.0122 (7) | 0.0036 (7) | −0.0050 (7) |
C12 | 0.0634 (9) | 0.0587 (9) | 0.0490 (8) | −0.0097 (7) | 0.0067 (7) | −0.0066 (7) |
C13 | 0.0493 (8) | 0.0507 (8) | 0.0502 (8) | 0.0022 (6) | 0.0024 (6) | 0.0048 (6) |
C14 | 0.0559 (10) | 0.1263 (19) | 0.0655 (11) | −0.0202 (11) | 0.0096 (8) | −0.0145 (11) |
C15 | 0.0576 (10) | 0.0771 (11) | 0.0562 (9) | 0.0025 (8) | 0.0027 (7) | −0.0002 (8) |
C16 | 0.0635 (10) | 0.0715 (10) | 0.0498 (8) | 0.0101 (8) | 0.0038 (7) | 0.0021 (7) |
C17 | 0.0630 (9) | 0.0626 (9) | 0.0542 (8) | 0.0175 (7) | 0.0099 (7) | 0.0112 (7) |
C18 | 0.0685 (11) | 0.0664 (10) | 0.0709 (11) | 0.0105 (8) | 0.0068 (9) | 0.0065 (9) |
C19 | 0.0694 (12) | 0.0785 (13) | 0.1027 (16) | 0.0024 (10) | 0.0053 (12) | 0.0108 (12) |
C20 | 0.0701 (14) | 0.0964 (16) | 0.1156 (19) | 0.0116 (12) | 0.0287 (13) | 0.0255 (15) |
C21 | 0.0844 (14) | 0.0926 (15) | 0.0789 (13) | 0.0264 (12) | 0.0319 (12) | 0.0192 (11) |
C22 | 0.0747 (11) | 0.0717 (11) | 0.0583 (9) | 0.0230 (9) | 0.0146 (8) | 0.0125 (8) |
C23 | 0.0758 (12) | 0.0872 (13) | 0.0574 (10) | 0.0115 (10) | 0.0012 (9) | −0.0036 (9) |
C24 | 0.135 (2) | 0.1115 (18) | 0.0537 (11) | 0.0424 (18) | 0.0092 (12) | −0.0068 (12) |
C25 | 0.125 (2) | 0.129 (3) | 0.107 (2) | 0.014 (2) | −0.0211 (19) | −0.0079 (18) |
C26 | 0.0777 (14) | 0.124 (2) | 0.0833 (15) | 0.0088 (13) | 0.0163 (12) | −0.0233 (14) |
N1 | 0.0506 (7) | 0.0789 (9) | 0.0530 (7) | −0.0036 (6) | 0.0094 (6) | −0.0055 (6) |
N2 | 0.0523 (7) | 0.0771 (9) | 0.0529 (7) | −0.0003 (6) | 0.0087 (6) | −0.0022 (6) |
N3 | 0.0914 (12) | 0.0889 (11) | 0.0487 (8) | 0.0250 (9) | 0.0101 (7) | −0.0006 (7) |
N4 | 0.1039 (19) | 0.301 (5) | 0.1065 (19) | 0.023 (2) | −0.0050 (16) | −0.055 (2) |
Geometric parameters (Å, º) top
C1—C2 | 1.383 (2) | C15—N2 | 1.280 (2) |
C1—C6 | 1.387 (2) | C15—C16 | 1.431 (2) |
C1—H1 | 0.924 (19) | C15—H15 | 0.98 (2) |
C2—C3 | 1.370 (3) | C16—C23 | 1.378 (3) |
C2—H2 | 0.98 (2) | C16—C17 | 1.446 (2) |
C3—C4 | 1.376 (3) | C17—C18 | 1.395 (3) |
C3—H3 | 0.96 (2) | C17—C22 | 1.409 (2) |
C4—C5 | 1.380 (3) | C18—C19 | 1.372 (3) |
C4—H4 | 0.99 (2) | C18—H18 | 0.982 (18) |
C5—C6 | 1.394 (2) | C19—C20 | 1.405 (4) |
C5—H5 | 0.94 (2) | C19—H19 | 0.93 (3) |
C6—C7 | 1.486 (2) | C20—C21 | 1.366 (4) |
C7—C12 | 1.388 (2) | C20—H20 | 0.92 (3) |
C7—C8 | 1.402 (2) | C21—C22 | 1.384 (3) |
C8—C9 | 1.380 (2) | C21—H21 | 0.98 (2) |
C8—H8 | 1.000 (19) | C22—N3 | 1.382 (3) |
C9—C10 | 1.395 (2) | C23—N3 | 1.354 (2) |
C9—H9 | 0.949 (19) | C23—H23 | 0.98 (2) |
C10—C11 | 1.390 (2) | C24—N3 | 1.458 (3) |
C10—C13 | 1.4836 (19) | C24—H24A | 0.9600 |
C11—C12 | 1.386 (2) | C24—H24B | 0.9600 |
C11—H11 | 0.927 (18) | C24—H24C | 0.9600 |
C12—H12 | 0.99 (2) | C25—C26 | 1.410 (4) |
C13—N1 | 1.287 (2) | C25—H25A | 0.9600 |
C13—C14 | 1.487 (2) | C25—H25B | 0.9600 |
C14—H14A | 0.9600 | C25—H25C | 0.9600 |
C14—H14B | 0.9600 | C26—N4 | 1.108 (3) |
C14—H14C | 0.9600 | N1—N2 | 1.4063 (17) |
| | | |
C2—C1—C6 | 121.41 (16) | N2—C15—C16 | 122.58 (17) |
C2—C1—H1 | 119.2 (11) | N2—C15—H15 | 119.7 (12) |
C6—C1—H1 | 119.4 (11) | C16—C15—H15 | 117.7 (12) |
C3—C2—C1 | 120.21 (17) | C23—C16—C15 | 124.00 (18) |
C3—C2—H2 | 121.6 (12) | C23—C16—C17 | 106.18 (16) |
C1—C2—H2 | 118.2 (12) | C15—C16—C17 | 129.82 (16) |
C2—C3—C4 | 119.46 (17) | C18—C17—C22 | 118.83 (18) |
C2—C3—H3 | 120.0 (13) | C18—C17—C16 | 135.01 (16) |
C4—C3—H3 | 120.4 (13) | C22—C17—C16 | 106.16 (17) |
C3—C4—C5 | 120.57 (18) | C19—C18—C17 | 118.8 (2) |
C3—C4—H4 | 120.0 (13) | C19—C18—H18 | 118.4 (11) |
C5—C4—H4 | 119.4 (13) | C17—C18—H18 | 122.7 (11) |
C4—C5—C6 | 120.84 (17) | C18—C19—C20 | 121.3 (3) |
C4—C5—H5 | 117.6 (14) | C18—C19—H19 | 120.7 (15) |
C6—C5—H5 | 121.5 (14) | C20—C19—H19 | 117.9 (15) |
C1—C6—C5 | 117.51 (15) | C21—C20—C19 | 120.9 (2) |
C1—C6—C7 | 121.71 (14) | C21—C20—H20 | 118.4 (17) |
C5—C6—C7 | 120.76 (14) | C19—C20—H20 | 120.7 (17) |
C12—C7—C8 | 117.10 (14) | C20—C21—C22 | 117.9 (2) |
C12—C7—C6 | 121.40 (13) | C20—C21—H21 | 121.7 (13) |
C8—C7—C6 | 121.46 (13) | C22—C21—H21 | 120.4 (13) |
C9—C8—C7 | 121.35 (14) | N3—C22—C21 | 129.5 (2) |
C9—C8—H8 | 117.7 (10) | N3—C22—C17 | 108.34 (17) |
C7—C8—H8 | 120.9 (10) | C21—C22—C17 | 122.2 (2) |
C8—C9—C10 | 121.31 (14) | N3—C23—C16 | 110.70 (19) |
C8—C9—H9 | 120.3 (11) | N3—C23—H23 | 120.4 (13) |
C10—C9—H9 | 118.4 (11) | C16—C23—H23 | 128.9 (13) |
C11—C10—C9 | 117.35 (14) | N3—C24—H24A | 109.5 |
C11—C10—C13 | 121.76 (14) | N3—C24—H24B | 109.5 |
C9—C10—C13 | 120.89 (13) | H24A—C24—H24B | 109.5 |
C12—C11—C10 | 121.38 (15) | N3—C24—H24C | 109.5 |
C12—C11—H11 | 120.4 (11) | H24A—C24—H24C | 109.5 |
C10—C11—H11 | 118.0 (11) | H24B—C24—H24C | 109.5 |
C11—C12—C7 | 121.49 (14) | C26—C25—H25A | 109.5 |
C11—C12—H12 | 118.4 (11) | C26—C25—H25B | 109.5 |
C7—C12—H12 | 119.8 (11) | H25A—C25—H25B | 109.5 |
N1—C13—C10 | 116.23 (13) | C26—C25—H25C | 109.5 |
N1—C13—C14 | 125.00 (15) | H25A—C25—H25C | 109.5 |
C10—C13—C14 | 118.77 (14) | H25B—C25—H25C | 109.5 |
C13—C14—H14A | 109.5 | N4—C26—C25 | 179.2 (4) |
C13—C14—H14B | 109.5 | C13—N1—N2 | 114.83 (13) |
H14A—C14—H14B | 109.5 | C15—N2—N1 | 111.13 (14) |
C13—C14—H14C | 109.5 | C23—N3—C22 | 108.62 (16) |
H14A—C14—H14C | 109.5 | C23—N3—C24 | 125.6 (2) |
H14B—C14—H14C | 109.5 | C22—N3—C24 | 125.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···N1 | 0.949 (19) | 2.440 (18) | 2.769 (2) | 100.1 (13) |
C14—H14C···N2 | 0.96 | 2.29 | 2.731 (2) | 107 |
Crystallographic data and structure refinements summary for 3-BEHMI topCompound | 3-BEHMI |
Chemical formula | C24H21N3.C2H3N |
Mr | 392.49 |
Crystal habit | block/yellow |
Crystal system | Monoclinic |
Space group | P21/c |
a (Å) | 8.1280 (2) |
b (Å) | 8.21470 (10) |
c (Å) | 32.9809 (6) |
α (°) | 90.00 |
β (°) | 90.252 (2) |
γ (°) | 90.00 |
V /Å3 | 2202.08 (7) |
Z | 4 |
Dcalc. (Mg m-3) | 1.184 |
µ (mm-1) | 0.071 |
T (K) | 298 |
F(000) | 832 |
Rint | 0.0395 |
R1 [I>2σ(I)] | 0.0525 |
wR2/reflections | 0.151/4300 |
S | 1.024 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000),
SHELXT2016 (Sheldrick, 2015a), SHELXL2016 (Sheldrick, 2015b),
SHELXTL (Bruker, 2000), PLATON (Spek, 2009), DIAMOND
(Brandenburg &
Putz, 1999) and ORTEP-3 (Farrugia, 2012). |
Selected C—H···π interaction geometry for 3-BEHEI [the H–centroid
distance (H···Cg), the perpendicular distance of H to plane I
(H-Perp), slippage angles between H···Cg and the normal to the plane
I (γ), the C—H···Cg angles (C—H···Cg), the
C–centroid distance (C···Cg), the angles between C—H bond line
and plane I (C—H···π)] (Å, °) topNotation | C—H···π (plane I) | H···Cg | H-Perp | γ | C—H···Cg | C···Cg | C—H···π |
a | C2—H2···Cg1i | 2.80 (2) | 2.679 | 16.69 | 159.7 (13) | 3.729 (2) | 60.31 |
b | C24—H24C···Cg1ii | 3.0934 | 2.713 | 28.71 | 146.48 | 3.930 (3) | 60.80 |
Ring 1 consists of atoms C17–C22
Symmetry codes: (i) -x+1, y-1/2, -z+1/2;
(ii) -x+2, -y+1, -. |
Inhibition of A549, 4T1 and MRC-5, NIH 3T3 cells growth by the title
compounds, compared with 3-BEHEI and Brequinar sodium topCompound | A549 cells, IC50 | 4T1 cells, IC50 | MRC-5 cells, IC50 | NIH 3T3 fibroblasts, IC50 |
3-BEHMI | 108.5±0.9 µM | 112.0±1.0 µM | 145.0±1.5 µM | 159.0±1.5 µM |
3-BEHEI | 50.5±0.7 µM | 52.0±0.9 µM | 78.5±0.9 µM | 79.0±1.2 µM |
3-BEHI | 21.5±0.6 µM | 18.0±0.6 µM | 28.0±0.7 µM | 22.0±0.8 µM |
Brequinar sodium | 12.6±0.5 nM | 9.9±0.4 nM | 18.0±0.3 nM | 15.5±0.5 nM |
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