A novel and potentially active dihydroorotate dehydrogenase (DHODH) inhibitor, namely 3-({(
E)-[(
E)-1-(biphenyl-4-yl)ethylidene]hydrazinylidene}methyl)-1
H-indole (BEHI) acetonitrile disolvate, C
23H
19N
3·2CH
3CN, has been designed and synthesized. The structure of BEHI was characterized by elemental analysis, Q-TOF (quadrupole time-of-flight) MS, NMR, UV–Vis and single-crystal X-ray diffraction. The antitumour activity of the target molecule was evaluated by the MTT method. Results indicated that BEHI exhibited rather potent cytotoxic activity against human A549 (IC
50 = 20.5 µ
M) and mouse breast 4T
1 (IC
50 = 18.5 µ
M) cancer cell lines. Meanwhile, to rationalize its potencies in the target, BEHI was docked into DHODH and the interactions with the active site residues were analyzed. Single-crystal structure analysis indicated that hydrogen bonds are present only between BEHI and acetonitrile solvent molecules in the asymmetric unit. The interplay of weak π–π stacking and weak C(N)—H
π interactions between neighbouring BEHI molecules play crucial roles in the formation of the final supramolecular frameworks.
Supporting information
CCDC reference: 1556543
Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXT2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: SHELXTL (Bruker, 2000), PLATON (Spek, 2009),
DIAMOND (Brandenburg & Putz, 1999) and ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).
3-({(
E)-[(
E)-1-(Biphenyl-4-yl)ethylidene]hydrazinylidene}methyl)-1
H-indole acetonitrile disolvate
top
Crystal data top
C23H19N3·2C2H3N | Dx = 1.171 Mg m−3 |
Mr = 419.52 | Melting point: 462.8(2) K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1493 (4) Å | Cell parameters from 380 reflections |
b = 8.5209 (5) Å | θ = 2.5–26.0° |
c = 34.4887 (14) Å | µ = 0.07 mm−1 |
β = 96.648 (4)° | T = 298 K |
V = 2378.8 (2) Å3 | Block, light yellow |
Z = 4 | 0.35 × 0.26 × 0.18 mm |
F(000) = 888 | |
Data collection top
Bruker SMART CCD area detector diffractometer | 5893 independent reflections |
Radiation source: fine-focus sealed tube | 3167 reflections with I > 2σ(I) |
Detector resolution: 10.24 pixels mm-1 | Rint = 0.076 |
phi and ω scans | θmax = 29.1°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −10→10 |
Tmin = 0.976, Tmax = 0.989 | k = −11→11 |
28460 measured reflections | l = −46→44 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: mixed |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.065P)2] where P = (Fo2 + 2Fc2)/3 |
5893 reflections | (Δ/σ)max < 0.001 |
368 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
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 | −0.1478 (2) | 0.5352 (2) | 0.19965 (5) | 0.0698 (5) | |
C2 | −0.2959 (3) | 0.5409 (3) | 0.17606 (6) | 0.0826 (6) | |
C3 | −0.3384 (2) | 0.4245 (3) | 0.14926 (5) | 0.0806 (5) | |
C4 | −0.2312 (2) | 0.3026 (2) | 0.14580 (5) | 0.0713 (5) | |
C5 | −0.0833 (2) | 0.2950 (2) | 0.16929 (4) | 0.0613 (4) | |
C6 | −0.03821 (18) | 0.41080 (17) | 0.19707 (4) | 0.0545 (4) | |
C7 | 0.11989 (18) | 0.40273 (17) | 0.22314 (4) | 0.0540 (4) | |
C8 | 0.1358 (2) | 0.46886 (19) | 0.26043 (4) | 0.0583 (4) | |
C9 | 0.28366 (19) | 0.46591 (19) | 0.28434 (5) | 0.0593 (4) | |
C10 | 0.42390 (17) | 0.39544 (17) | 0.27222 (4) | 0.0540 (4) | |
C11 | 0.4069 (2) | 0.3258 (2) | 0.23536 (5) | 0.0635 (4) | |
C12 | 0.2587 (2) | 0.3302 (2) | 0.21148 (5) | 0.0619 (4) | |
C13 | 0.58273 (18) | 0.39466 (18) | 0.29784 (4) | 0.0560 (4) | |
C14 | 0.7227 (3) | 0.2999 (3) | 0.28593 (7) | 0.0842 (6) | |
C15 | 0.7367 (2) | 0.5542 (2) | 0.38395 (5) | 0.0662 (4) | |
C16 | 0.8766 (2) | 0.56975 (19) | 0.41290 (5) | 0.0633 (4) | |
C17 | 0.8737 (3) | 0.6521 (3) | 0.44720 (5) | 0.0792 (5) | |
C18 | 1.1287 (2) | 0.5547 (2) | 0.44929 (5) | 0.0728 (5) | |
C19 | 1.2920 (3) | 0.5148 (3) | 0.46008 (7) | 0.0911 (7) | |
C20 | 1.3703 (3) | 0.4266 (3) | 0.43478 (7) | 0.0945 (7) | |
C21 | 1.2857 (2) | 0.3770 (3) | 0.39924 (6) | 0.0846 (6) | |
C22 | 1.1233 (2) | 0.4149 (2) | 0.38867 (5) | 0.0696 (5) | |
C23 | 1.0405 (2) | 0.50537 (19) | 0.41393 (4) | 0.0629 (4) | |
C24 | 1.1844 (4) | 0.9272 (4) | 0.61211 (7) | 0.1166 (8) | |
H24A | 1.0799 | 0.9311 | 0.6224 | 0.231 (19)* | |
H24B | 1.2291 | 1.0312 | 0.6114 | 0.191 (14)* | |
H24C | 1.2593 | 0.8619 | 0.6285 | 0.221 (17)* | |
C25 | 1.1617 (3) | 0.8632 (3) | 0.57327 (6) | 0.0886 (6) | |
C26 | 0.2515 (4) | 1.0066 (4) | 0.45680 (10) | 0.1259 (9) | |
H26A | 0.2460 | 1.0430 | 0.4830 | 0.27 (3)* | |
H26B | 0.1669 | 0.9296 | 0.4502 | 0.26 (2)* | |
H26C | 0.2354 | 1.0935 | 0.4390 | 0.243 (19)* | |
C27 | 0.4108 (4) | 0.9374 (3) | 0.45413 (7) | 0.1073 (8) | |
N1 | 0.58785 (15) | 0.47591 (17) | 0.32937 (4) | 0.0663 (4) | |
N2 | 0.74129 (15) | 0.47184 (17) | 0.35301 (4) | 0.0666 (4) | |
N3 | 1.0229 (2) | 0.6429 (2) | 0.46890 (5) | 0.0873 (5) | |
N4 | 0.5344 (4) | 0.8839 (4) | 0.45153 (8) | 0.1572 (11) | |
N5 | 1.1409 (3) | 0.8135 (3) | 0.54300 (6) | 0.1304 (8) | |
H1 | −0.119 (2) | 0.621 (2) | 0.2191 (5) | 0.093 (6)* | |
H2 | −0.367 (2) | 0.624 (2) | 0.1781 (6) | 0.094 (6)* | |
H3 | −0.447 (2) | 0.427 (2) | 0.1330 (5) | 0.085 (5)* | |
H3N | 1.049 (3) | 0.691 (3) | 0.4924 (7) | 0.113 (7)* | |
H4 | −0.259 (2) | 0.221 (2) | 0.1274 (5) | 0.082 (5)* | |
H5 | −0.0090 (18) | 0.204 (2) | 0.1671 (4) | 0.071 (5)* | |
H8 | 0.049 (2) | 0.5153 (19) | 0.2707 (5) | 0.069 (5)* | |
H9 | 0.2941 (19) | 0.513 (2) | 0.3102 (5) | 0.074 (5)* | |
H11 | 0.500 (2) | 0.277 (2) | 0.2264 (5) | 0.079 (5)* | |
H12 | 0.2510 (18) | 0.283 (2) | 0.1859 (5) | 0.076 (5)* | |
H14A | 0.751 (3) | 0.339 (3) | 0.2587 (8) | 0.126 (8)* | |
H14B | 0.696 (4) | 0.186 (4) | 0.2798 (9) | 0.167 (12)* | |
H14C | 0.820 (3) | 0.305 (3) | 0.3043 (6) | 0.107 (7)* | |
H15 | 0.633 (2) | 0.613 (2) | 0.3886 (5) | 0.083 (5)* | |
H17 | 0.785 (2) | 0.712 (3) | 0.4555 (6) | 0.096 (6)* | |
H19 | 1.348 (2) | 0.552 (2) | 0.4834 (6) | 0.093 (6)* | |
H20 | 1.489 (3) | 0.393 (2) | 0.4418 (5) | 0.096 (6)* | |
H21 | 1.344 (2) | 0.310 (2) | 0.3817 (6) | 0.091 (6)* | |
H22 | 1.0664 (19) | 0.382 (2) | 0.3637 (5) | 0.074 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0843 (12) | 0.0597 (11) | 0.0643 (10) | 0.0098 (9) | 0.0037 (8) | −0.0079 (8) |
C2 | 0.0895 (13) | 0.0822 (14) | 0.0740 (12) | 0.0282 (11) | −0.0002 (10) | −0.0089 (10) |
C3 | 0.0760 (12) | 0.0916 (15) | 0.0712 (12) | 0.0118 (11) | −0.0039 (9) | −0.0053 (10) |
C4 | 0.0805 (11) | 0.0673 (12) | 0.0637 (10) | 0.0010 (9) | −0.0011 (8) | −0.0101 (9) |
C5 | 0.0745 (10) | 0.0540 (10) | 0.0556 (9) | 0.0026 (8) | 0.0079 (7) | −0.0017 (7) |
C6 | 0.0664 (9) | 0.0480 (9) | 0.0502 (8) | −0.0020 (7) | 0.0112 (6) | 0.0027 (6) |
C7 | 0.0649 (9) | 0.0449 (8) | 0.0531 (8) | −0.0041 (7) | 0.0110 (7) | −0.0001 (6) |
C8 | 0.0610 (9) | 0.0568 (10) | 0.0587 (9) | −0.0001 (7) | 0.0132 (7) | −0.0075 (7) |
C9 | 0.0659 (10) | 0.0584 (10) | 0.0547 (9) | −0.0030 (8) | 0.0115 (7) | −0.0084 (7) |
C10 | 0.0617 (9) | 0.0467 (9) | 0.0546 (8) | −0.0025 (7) | 0.0116 (7) | 0.0012 (6) |
C11 | 0.0702 (10) | 0.0623 (11) | 0.0594 (9) | 0.0066 (8) | 0.0141 (8) | −0.0045 (7) |
C12 | 0.0744 (10) | 0.0586 (10) | 0.0530 (9) | 0.0036 (8) | 0.0093 (7) | −0.0082 (7) |
C13 | 0.0639 (9) | 0.0504 (9) | 0.0552 (9) | −0.0032 (7) | 0.0139 (7) | 0.0043 (7) |
C14 | 0.0711 (12) | 0.1059 (19) | 0.0751 (13) | 0.0178 (11) | 0.0068 (10) | −0.0137 (12) |
C15 | 0.0712 (11) | 0.0617 (11) | 0.0659 (10) | −0.0047 (9) | 0.0090 (8) | 0.0017 (8) |
C16 | 0.0733 (11) | 0.0586 (10) | 0.0582 (9) | −0.0081 (8) | 0.0092 (7) | −0.0006 (7) |
C17 | 0.0902 (13) | 0.0800 (14) | 0.0674 (11) | −0.0047 (11) | 0.0089 (10) | −0.0079 (9) |
C18 | 0.0828 (12) | 0.0729 (12) | 0.0612 (10) | −0.0135 (9) | 0.0017 (9) | 0.0036 (8) |
C19 | 0.0868 (14) | 0.1062 (18) | 0.0752 (13) | −0.0170 (12) | −0.0118 (11) | 0.0055 (12) |
C20 | 0.0773 (13) | 0.1102 (18) | 0.0932 (15) | −0.0061 (12) | −0.0015 (12) | 0.0142 (13) |
C21 | 0.0811 (13) | 0.0898 (15) | 0.0847 (13) | 0.0006 (11) | 0.0174 (11) | 0.0083 (11) |
C22 | 0.0752 (11) | 0.0710 (12) | 0.0628 (11) | −0.0079 (9) | 0.0087 (9) | 0.0029 (9) |
C23 | 0.0732 (10) | 0.0586 (10) | 0.0564 (9) | −0.0163 (8) | 0.0052 (7) | 0.0067 (7) |
C24 | 0.151 (2) | 0.120 (2) | 0.0767 (14) | −0.0237 (19) | 0.0050 (15) | −0.0135 (13) |
C25 | 0.1088 (14) | 0.0845 (15) | 0.0727 (13) | −0.0190 (11) | 0.0108 (10) | −0.0018 (11) |
C26 | 0.114 (2) | 0.133 (3) | 0.132 (2) | 0.0109 (19) | 0.0189 (15) | 0.027 (2) |
C27 | 0.1092 (19) | 0.118 (2) | 0.0920 (15) | −0.0079 (17) | −0.0014 (13) | 0.0032 (13) |
N1 | 0.0635 (8) | 0.0700 (9) | 0.0641 (8) | 0.0022 (7) | 0.0022 (6) | −0.0071 (7) |
N2 | 0.0672 (8) | 0.0686 (9) | 0.0630 (8) | 0.0004 (7) | 0.0031 (6) | −0.0042 (7) |
N3 | 0.1024 (12) | 0.0956 (13) | 0.0617 (10) | −0.0098 (9) | 0.0000 (9) | −0.0142 (9) |
N4 | 0.1214 (18) | 0.180 (3) | 0.165 (2) | 0.0192 (18) | −0.0043 (16) | −0.033 (2) |
N5 | 0.181 (2) | 0.1318 (19) | 0.0803 (13) | −0.0445 (15) | 0.0230 (12) | −0.0219 (13) |
Geometric parameters (Å, º) top
C1—C2 | 1.376 (3) | C15—C16 | 1.432 (2) |
C1—C6 | 1.395 (2) | C15—H15 | 1.013 (19) |
C1—H1 | 1.00 (2) | C16—C17 | 1.378 (2) |
C2—C3 | 1.372 (3) | C16—C23 | 1.440 (2) |
C2—H2 | 0.92 (2) | C17—N3 | 1.354 (3) |
C3—C4 | 1.372 (3) | C17—H17 | 0.96 (2) |
C3—H3 | 0.990 (18) | C18—N3 | 1.379 (3) |
C4—C5 | 1.374 (2) | C18—C19 | 1.382 (3) |
C4—H4 | 0.952 (19) | C18—C23 | 1.406 (2) |
C5—C6 | 1.394 (2) | C19—C20 | 1.364 (3) |
C5—H5 | 0.991 (17) | C19—H19 | 0.93 (2) |
C6—C7 | 1.485 (2) | C20—C21 | 1.400 (3) |
C7—C12 | 1.389 (2) | C20—H20 | 1.01 (2) |
C7—C8 | 1.396 (2) | C21—C22 | 1.370 (3) |
C8—C9 | 1.379 (2) | C21—H21 | 0.99 (2) |
C8—H8 | 0.915 (17) | C22—C23 | 1.395 (2) |
C9—C10 | 1.397 (2) | C22—H22 | 0.971 (17) |
C9—H9 | 0.974 (18) | C24—C25 | 1.438 (3) |
C10—C11 | 1.395 (2) | C24—H24A | 0.9600 |
C10—C13 | 1.480 (2) | C24—H24B | 0.9600 |
C11—C12 | 1.381 (2) | C24—H24C | 0.9600 |
C11—H11 | 0.947 (18) | C25—N5 | 1.121 (2) |
C12—H12 | 0.966 (17) | C26—C27 | 1.438 (4) |
C13—N1 | 1.2855 (18) | C26—H26A | 0.9600 |
C13—C14 | 1.493 (2) | C26—H26B | 0.9600 |
C14—H14A | 1.05 (3) | C26—H26C | 0.9600 |
C14—H14B | 1.01 (4) | C27—N4 | 1.118 (3) |
C14—H14C | 0.96 (2) | N1—N2 | 1.4119 (17) |
C15—N2 | 1.281 (2) | N3—H3N | 0.91 (2) |
| | | |
C2—C1—C6 | 120.91 (17) | N2—C15—H15 | 120.6 (10) |
C2—C1—H1 | 119.6 (10) | C16—C15—H15 | 117.1 (10) |
C6—C1—H1 | 119.5 (10) | C17—C16—C15 | 123.67 (17) |
C3—C2—C1 | 120.52 (19) | C17—C16—C23 | 106.31 (15) |
C3—C2—H2 | 119.8 (12) | C15—C16—C23 | 130.00 (15) |
C1—C2—H2 | 119.7 (12) | N3—C17—C16 | 109.97 (19) |
C4—C3—C2 | 119.52 (18) | N3—C17—H17 | 121.9 (12) |
C4—C3—H3 | 119.9 (10) | C16—C17—H17 | 128.1 (12) |
C2—C3—H3 | 120.6 (10) | N3—C18—C19 | 129.75 (18) |
C3—C4—C5 | 120.54 (18) | N3—C18—C23 | 107.61 (16) |
C3—C4—H4 | 120.5 (10) | C19—C18—C23 | 122.6 (2) |
C5—C4—H4 | 119.0 (10) | C20—C19—C18 | 118.0 (2) |
C4—C5—C6 | 121.04 (17) | C20—C19—H19 | 121.5 (12) |
C4—C5—H5 | 119.5 (9) | C18—C19—H19 | 120.4 (12) |
C6—C5—H5 | 119.4 (9) | C19—C20—C21 | 120.5 (2) |
C5—C6—C1 | 117.46 (15) | C19—C20—H20 | 120.7 (11) |
C5—C6—C7 | 121.63 (14) | C21—C20—H20 | 118.8 (11) |
C1—C6—C7 | 120.91 (14) | C22—C21—C20 | 121.6 (2) |
C12—C7—C8 | 117.02 (14) | C22—C21—H21 | 119.5 (11) |
C12—C7—C6 | 121.61 (13) | C20—C21—H21 | 118.9 (11) |
C8—C7—C6 | 121.38 (14) | C21—C22—C23 | 119.10 (18) |
C9—C8—C7 | 121.66 (15) | C21—C22—H22 | 121.1 (10) |
C9—C8—H8 | 115.8 (10) | C23—C22—H22 | 119.8 (10) |
C7—C8—H8 | 122.5 (10) | C22—C23—C18 | 118.13 (17) |
C8—C9—C10 | 121.15 (15) | C22—C23—C16 | 135.19 (15) |
C8—C9—H9 | 121.2 (9) | C18—C23—C16 | 106.66 (16) |
C10—C9—H9 | 117.7 (9) | C25—C24—H24A | 109.5 |
C11—C10—C9 | 117.18 (14) | C25—C24—H24B | 109.5 |
C11—C10—C13 | 121.99 (14) | H24A—C24—H24B | 109.5 |
C9—C10—C13 | 120.82 (13) | C25—C24—H24C | 109.5 |
C12—C11—C10 | 121.31 (16) | H24A—C24—H24C | 109.5 |
C12—C11—H11 | 119.8 (10) | H24B—C24—H24C | 109.5 |
C10—C11—H11 | 118.9 (10) | N5—C25—C24 | 178.7 (3) |
C11—C12—C7 | 121.64 (15) | C27—C26—H26A | 109.5 |
C11—C12—H12 | 119.6 (9) | C27—C26—H26B | 109.5 |
C7—C12—H12 | 118.8 (9) | H26A—C26—H26B | 109.5 |
N1—C13—C10 | 116.29 (13) | C27—C26—H26C | 109.5 |
N1—C13—C14 | 124.95 (15) | H26A—C26—H26C | 109.5 |
C10—C13—C14 | 118.75 (15) | H26B—C26—H26C | 109.5 |
C13—C14—H14A | 109.0 (13) | N4—C27—C26 | 179.1 (3) |
C13—C14—H14B | 115.1 (17) | C13—N1—N2 | 114.52 (13) |
H14A—C14—H14B | 101 (2) | C15—N2—N1 | 111.00 (13) |
C13—C14—H14C | 113.0 (13) | C17—N3—C18 | 109.44 (16) |
H14A—C14—H14C | 109.3 (18) | C17—N3—H3N | 124.7 (14) |
H14B—C14—H14C | 109 (2) | C18—N3—H3N | 125.8 (14) |
N2—C15—C16 | 122.29 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14C···N2 | 0.96 (2) | 2.34 (2) | 2.728 (3) | 103.3 (15) |
C9—H9···N1 | 0.974 (18) | 2.430 (15) | 2.770 (2) | 100.0 (11) |
C17—H17···N4 | 0.96 (2) | 2.50 (2) | 3.416 (4) | 159.6 (16) |
N3—H3N···N5 | 0.91 (2) | 2.10 (2) | 3.000 (3) | 171.2 (19) |
Table 2. Selected π–π interaction geometry for BEHI topd is the the centroid–centroid distance;
α is the dihedral angle;
β is the slippage angles between the centroid–centroid distance and the
normal to plane I;
γ is the slippage angles between the centroid–centroid distance and the
normal to tplane J;
e is the the perpendicular distance of centroid I to
plane J;
f is the perpendicular distance of centroid J to plane I. |
π–π interactions (I → J) | d (Å) | α (°) | β (°) | γ (°) | e (Å) | f (Å) |
Cg1→Cg1#1 | 4.4695 (11) | 0.00 | 44.63 | 44.63 | 3.181 | 3.181 |
Cg1→Cg2#2 | 5.1886 (11) | 86.42 | 23.31 | 64.57 | 2.228 | 4.765 |
Cg1→Cg4#1 | 5.1826 (12) | 0.78 | 51.94 | 52.53 | 3.153 | 3.195 |
Cg2→Cg3#3 | 5.3543 (10) | 29.17 | 36.81 | 60.77 | 2.614 | 4.287 |
Cg2→Cg3#4 | 5.2907 (11) | 89.12 | 28.70 | 62.19 | 2.469 | 4.641 |
Cg2→Cg4#2 | 5.7358 (12) | 87.13 | 33.37 | 66.05 | 2.328 | 4.790 |
Cg3→Cg2#4 | 5.0087 (11) | 89.12 | 11.28 | 86.91 | 0.270 | 4.912 |
Cg3→Cg3#2 | 5.6496 (10) | 59.96 | 32.06 | 62.68 | 2.593 | 4.788 |
Cg4→Cg1#1 | 5.1827 (12) | 0.78 | 52.53 | 51.94 | 3.195 | 3.153 |
Cg4→Cg2#2 | 5.1006 (12) | 87.13 | 21.09 | 85.28 | 0.420 | 4.759 |
Notes: ring 1 is N3—C17—C16—C23—C18, ring 2 is C1–C6,
ring 3 is C7–C12 and ring 4 is C18–C23. Symmetry codes:
(#1) -x, -y+2, -z;
(#2) -x+1, y+1/2, -z+1/2;
(#3) x+1, y, z;
(#4) -x+2, y-1/2, -z+1/2. |
Selected C—H···π and N—H···π interaction geometry for BEHI. topH···Cg is the distance between a H atom and the centroid of the benzene
ring; H-Perp is the perpendicular distances of a H atom to the benzene-ring
plane; γ is the slipping angle between the X—H distance and the
normal to the benzene plane; X—H···Cg is the
X—H···centroid angle; X···Cg is the X—centroid
distance. |
C—H···π interactions | H···Cg (Å) | H-Perp (Å) | γ (°) | X—H···Cg (°) | X···Cg (Å) |
C1—H1···Cg3#1 | 2.958 (17) | 2.917 | 9.61 | 139.9 (12) | 3.7795 (18) |
C4—H4···Cg4#2 | 2.877 (17) | 2.805 | 12.83 | 157.8 (13) | 3.7748 (19) |
C14—H14A···Cg2#3 | 3.13 (3) | 2.785 | 27.15 | 172.7 (18) | 4.170 (3) |
C14—H14B···Cg3#2 | 2.66 (3) | 2.619 | 10.54 | 159 (2) | 3.618 (3) |
N3—H3N···Cg1#4 | 3.39 (2) | 3.198 | 19.29 | 106.5 (17) | 3.7496 (19) |
C24—H24A···Cg2#2 | 3.220 | 3.086 | 16.60 | 154.40 | 4.107 (3) |
C26—H26C···Cg4#5 | 3.215 | 2.800 | 29.42 | 149.58 | 4.072 (4) |
Notes: ring 1 is N3—C17—C16—C23—C18;
ring 2 is C1–C6;
ring 3 is C7–C12;
ring 4 is C18–C23.
Symmetry codes:
(#1) -x+2, y+1/2, -z+1/2;
(#2) -x+1, y-1/2, -z+1/2;
(#3) x-1, y, z;
(#4) -x, -y+2, -z;
(#5) x+1, y, z. |
Inhibition of A549 and 4T1 cells growth by BEHI compared with
Brequinar sodium topCompound | A549 cells, IC50 | 4T1 cells, IC50 |
BEHI | 20.5±0.6 µM | 18.5±0.4 µM |
Brequinar sodium | 12.3±0.5 nM | 9.5±0.4 nM |