Literature DB >> 21588259

1-{6-Chloro-2-[(2-chloro-8-methyl-3-quinol-yl)meth-oxy]-4-phenyl-quinolin-3-yl}ethanone.

F Nawaz Khan, Venkatesha R Hathwar, Rajesh Kumar, A Sudheer Kumar, Mehmet Akkurt.   

Abstract

In the title mol-ecule, C(28)H(20)Cl(2)N(2)O(2), the dihedral angle between the 2-chloro-quinoline and 6-chloro-quinoline rings is 7.55 (6)°. The dihedral angle between the phenyl ring and its attached quinoline ring is 62.59 (4)°. In the crystal, aromatic π-π stacking inter-actions [centroid-centroid distances = 3.771 (3) and 3.612 (3) Å] help to establish the packing.

Entities:  

Year:  2010        PMID： 21588259      PMCID： PMC3007527          DOI： 10.1107/S160053681002595X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the structures of related 2-quinolone compounds, see: Khan, Roopan, Hathwar et al. (2010 ▶); Khan, Roopan, Kumar et al. (2010 ▶). For the biological activity, see: Ukita & Mizuno (1960 ▶); Jayashree et al. (2010 ▶); Joseph et al. (2002 ▶); Xiao et al. (2001 ▶). For related literature, see: Roopan & Khan (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C28H20Cl2N2O2 M = 487.36 Triclinic, a = 9.7396 (4) Å b = 10.5520 (3) Å c = 13.0108 (4) Å α = 88.730 (3)° β = 68.127 (4)° γ = 71.105 (4)° V = 1166.62 (8) Å3 Z = 2 Mo Kα radiation μ = 0.31 mm−1 T = 295 K 0.24 × 0.18 × 0.15 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T min = 0.930, T max = 0.955 22437 measured reflections 4323 independent reflections 2707 reflections with I > 2σ(I) R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.099 S = 0.95 4323 reflections 309 parameters H-atom parameters constrained Δρmax = 0.17 e Å−3 Δρmin = −0.20 e Å−3 Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002595X/lx2158sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053681002595X/lx2158Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C28H20Cl2N2O2Z = 2
Mr = 487.36F(000) = 504
Triclinic, P1Dx = 1.387 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7396 (4) ÅCell parameters from 1523 reflections
b = 10.5520 (3) Åθ = 1.9–21.4°
c = 13.0108 (4) ŵ = 0.31 mm−1
α = 88.730 (3)°T = 295 K
β = 68.127 (4)°Block, colourless
γ = 71.105 (4)°0.24 × 0.18 × 0.15 mm
V = 1166.62 (8) Å3
Oxford Xcalibur Eos (Nova) CCD detector diffractometer4323 independent reflections
Radiation source: Enhance (Mo) X-ray Source2707 reflections with I > 2σ(I)
graphiteRint = 0.043
ω scansθmax = 25.5°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)h = −11→11
Tmin = 0.930, Tmax = 0.955k = −12→12
22437 measured reflectionsl = −15→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: difference Fourier map
wR(F2) = 0.099H-atom parameters constrained
S = 0.95w = 1/[σ2(Fo2) + (0.0508P)2] where P = (Fo2 + 2Fc2)/3
4323 reflections(Δ/σ)max < 0.001
309 parametersΔρmax = 0.17 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.
xyzUiso*/Ueq
Cl10.16697 (6)0.85124 (6)1.16788 (4)0.0619 (2)
Cl20.24300 (8)0.10446 (6)0.58993 (5)0.0766 (3)
O10.8426 (2)0.46569 (18)0.71113 (15)0.0882 (8)
O20.51617 (15)0.59876 (14)0.85708 (11)0.0569 (5)
N10.40686 (19)0.91617 (16)1.15591 (12)0.0469 (6)
N20.34893 (19)0.50251 (15)0.83264 (13)0.0467 (6)
C10.3644 (2)0.83966 (19)1.10679 (15)0.0442 (7)
C20.4616 (2)0.74620 (18)1.01018 (15)0.0439 (7)
C30.6156 (2)0.73538 (19)0.96840 (15)0.0478 (7)
C40.6722 (2)0.81378 (19)1.01774 (15)0.0453 (7)
C50.8312 (2)0.8047 (2)0.97723 (17)0.0556 (8)
C60.8776 (3)0.8850 (2)1.02774 (19)0.0640 (9)
C70.7671 (3)0.9777 (2)1.11959 (18)0.0610 (9)
C80.6118 (3)0.9910 (2)1.16341 (16)0.0514 (8)
C90.5621 (2)0.90695 (19)1.11163 (15)0.0441 (7)
C100.4943 (3)1.0894 (2)1.26265 (18)0.0675 (9)
C110.3932 (2)0.6686 (2)0.96029 (15)0.0522 (7)
C120.4862 (2)0.51534 (18)0.79707 (16)0.0442 (7)
C130.6141 (2)0.45183 (18)0.69549 (15)0.0421 (7)
C140.5961 (2)0.36140 (18)0.63171 (15)0.0404 (6)
C150.4501 (2)0.33709 (18)0.67024 (15)0.0413 (7)
C160.4214 (2)0.2410 (2)0.61547 (16)0.0477 (7)
C170.2772 (3)0.2266 (2)0.65504 (17)0.0514 (8)
C180.1544 (3)0.3075 (2)0.74891 (18)0.0577 (8)
C190.1802 (2)0.3982 (2)0.80495 (17)0.0529 (8)
C200.3284 (2)0.41356 (19)0.76929 (16)0.0430 (7)
C210.7258 (2)0.29310 (18)0.52394 (15)0.0411 (7)
C220.7071 (2)0.3150 (2)0.42376 (17)0.0540 (8)
C230.8307 (3)0.2580 (2)0.32397 (17)0.0645 (9)
C240.9741 (3)0.1765 (2)0.32318 (18)0.0651 (9)
C250.9930 (3)0.1522 (2)0.42123 (18)0.0635 (8)
C260.8697 (2)0.2107 (2)0.52146 (17)0.0536 (8)
C270.7577 (2)0.4940 (2)0.66076 (18)0.0524 (7)
C280.7825 (3)0.5774 (2)0.56593 (19)0.0723 (9)
H30.685300.674700.905700.0570*
H50.904700.743500.915800.0670*
H60.982800.878301.001200.0770*
H70.801101.032601.152200.0730*
H10A0.546101.138501.287200.1010*
H10B0.447701.041601.321700.1010*
H10C0.413801.151201.242600.1010*
H11A0.358800.605001.009700.0630*
H11B0.303700.729100.947200.0630*
H160.501100.187100.552000.0570*
H180.055400.299100.772900.0690*
H190.098500.451200.868000.0630*
H220.610100.368700.423900.0650*
H230.817500.274600.257200.0770*
H241.057700.138100.255900.0780*
H251.089200.096100.420700.0760*
H260.884100.194200.587900.0640*
H28A0.866500.610000.558900.1090*
H28B0.687700.652400.579500.1090*
H28C0.809200.523400.498300.1090*
U11U22U33U12U13U23
Cl10.0520 (3)0.0709 (4)0.0580 (4)−0.0276 (3)−0.0098 (3)−0.0047 (3)
Cl20.0897 (5)0.0851 (5)0.0828 (5)−0.0534 (4)−0.0430 (4)0.0057 (3)
O10.0757 (12)0.1028 (14)0.1176 (15)−0.0422 (10)−0.0617 (12)0.0225 (11)
O20.0572 (9)0.0598 (9)0.0529 (9)−0.0249 (7)−0.0152 (7)−0.0134 (7)
N10.0549 (11)0.0459 (10)0.0428 (10)−0.0199 (8)−0.0197 (8)0.0048 (8)
N20.0471 (10)0.0458 (10)0.0478 (10)−0.0193 (8)−0.0161 (8)0.0052 (8)
C10.0488 (12)0.0439 (11)0.0408 (12)−0.0193 (10)−0.0156 (10)0.0086 (10)
C20.0510 (13)0.0422 (11)0.0408 (11)−0.0184 (10)−0.0181 (10)0.0062 (9)
C30.0511 (13)0.0486 (12)0.0386 (11)−0.0150 (10)−0.0134 (10)0.0014 (9)
C40.0524 (13)0.0504 (12)0.0379 (11)−0.0206 (10)−0.0202 (10)0.0116 (9)
C50.0545 (14)0.0657 (15)0.0462 (13)−0.0266 (12)−0.0140 (11)0.0126 (11)
C60.0617 (15)0.0831 (18)0.0611 (15)−0.0396 (14)−0.0269 (13)0.0222 (13)
C70.0809 (17)0.0671 (15)0.0625 (15)−0.0458 (14)−0.0407 (14)0.0208 (12)
C80.0672 (15)0.0516 (13)0.0487 (13)−0.0302 (12)−0.0286 (11)0.0145 (10)
C90.0558 (13)0.0446 (12)0.0395 (11)−0.0217 (10)−0.0229 (10)0.0114 (9)
C100.0873 (17)0.0623 (15)0.0627 (15)−0.0309 (13)−0.0346 (13)−0.0014 (12)
C110.0544 (13)0.0519 (12)0.0483 (13)−0.0168 (11)−0.0183 (11)−0.0042 (10)
C120.0500 (13)0.0403 (11)0.0458 (12)−0.0172 (10)−0.0207 (10)0.0025 (9)
C130.0418 (11)0.0413 (11)0.0450 (12)−0.0144 (9)−0.0185 (9)0.0062 (9)
C140.0448 (11)0.0386 (11)0.0411 (11)−0.0144 (9)−0.0201 (9)0.0060 (9)
C150.0486 (12)0.0386 (11)0.0418 (11)−0.0174 (9)−0.0212 (10)0.0098 (9)
C160.0550 (13)0.0499 (12)0.0447 (12)−0.0227 (11)−0.0222 (10)0.0075 (9)
C170.0618 (14)0.0523 (13)0.0585 (14)−0.0310 (12)−0.0337 (12)0.0147 (11)
C180.0505 (13)0.0629 (15)0.0703 (16)−0.0301 (12)−0.0261 (12)0.0192 (12)
C190.0463 (13)0.0521 (13)0.0592 (14)−0.0206 (11)−0.0161 (11)0.0068 (10)
C200.0474 (12)0.0401 (11)0.0464 (12)−0.0196 (10)−0.0197 (10)0.0118 (9)
C210.0455 (12)0.0387 (11)0.0418 (12)−0.0178 (9)−0.0168 (10)0.0040 (9)
C220.0565 (13)0.0517 (13)0.0523 (14)−0.0123 (11)−0.0245 (11)0.0033 (10)
C230.0849 (18)0.0627 (15)0.0420 (13)−0.0204 (14)−0.0241 (13)0.0041 (11)
C240.0752 (17)0.0533 (14)0.0475 (14)−0.0153 (13)−0.0081 (12)−0.0024 (11)
C250.0551 (14)0.0559 (14)0.0611 (16)−0.0030 (11)−0.0159 (12)0.0009 (12)
C260.0556 (14)0.0545 (13)0.0464 (13)−0.0124 (11)−0.0205 (11)0.0053 (10)
C270.0436 (12)0.0462 (12)0.0654 (14)−0.0130 (10)−0.0201 (11)−0.0070 (10)
C280.0627 (15)0.0676 (15)0.0818 (17)−0.0323 (13)−0.0143 (13)0.0140 (13)
Cl1—C11.749 (2)C18—C191.354 (3)
Cl2—C171.740 (3)C19—C201.405 (3)
O1—C271.199 (3)C21—C221.386 (3)
O2—C111.433 (2)C21—C261.378 (3)
O2—C121.355 (2)C22—C231.378 (3)
N1—C11.291 (3)C23—C241.379 (4)
N1—C91.373 (3)C24—C251.363 (3)
N2—C121.294 (3)C25—C261.383 (3)
N2—C201.371 (3)C27—C281.491 (3)
C1—C21.419 (3)C3—H30.9300
C2—C31.357 (3)C5—H50.9300
C2—C111.495 (3)C6—H60.9300
C3—C41.408 (3)C7—H70.9300
C4—C51.408 (3)C10—H10A0.9600
C4—C91.415 (3)C10—H10B0.9600
C5—C61.359 (3)C10—H10C0.9600
C6—C71.398 (3)C11—H11A0.9700
C7—C81.362 (4)C11—H11B0.9700
C8—C91.422 (3)C16—H160.9300
C8—C101.498 (3)C18—H180.9300
C12—C131.421 (3)C19—H190.9300
C13—C141.372 (3)C22—H220.9300
C13—C271.511 (3)C23—H230.9300
C14—C151.428 (3)C24—H240.9300
C14—C211.489 (3)C25—H250.9300
C15—C161.406 (3)C26—H260.9300
C15—C201.416 (3)C28—H28A0.9600
C16—C171.363 (4)C28—H28B0.9600
C17—C181.396 (3)C28—H28C0.9600
Cl1···C24i3.563 (2)C13···H263.0100
Cl1···H11A2.9500C15···H223.0600
Cl1···H11B2.8100C16···H10Biii3.0600
Cl1···H24i2.9600C16···H223.0700
Cl1···H18ii2.9500C21···H162.6700
Cl1···H26iii3.0800C21···H28C2.7800
Cl2···H25iv3.1100C22···H28C3.0000
O1···O22.901 (2)C22···H162.7900
O1···C18v3.169 (4)C24···H5ix3.0900
O2···O12.901 (2)C27···H263.0300
O1···H18v2.6200H3···O22.3300
O2···H32.3300H3···H52.5200
N1···H10B2.7700H5···H32.5200
N1···H10C2.7800H5···C24ix3.0900
N2···H11A2.6100H5···H24ix2.5000
N2···H11B2.6700H7···H10A2.3500
N2···H23vi2.8900H10A···H72.3500
C2···C8vii3.598 (3)H10B···N12.7700
C4···C19iii3.543 (3)H10B···C16iii3.0600
C5···C19iii3.504 (3)H10C···N12.7800
C6···C18iii3.484 (3)H10C···C3vii3.0400
C7···C18iii3.439 (3)H11A···Cl12.9500
C7···C17iii3.579 (3)H11A···N22.6100
C8···C2vii3.598 (3)H11B···Cl12.8100
C8···C17iii3.475 (3)H11B···N22.6700
C16···C223.275 (3)H16···C212.6700
C17···C7iii3.579 (3)H16···C222.7900
C17···C8iii3.475 (3)H18···O1iv2.6200
C18···O1iv3.169 (4)H18···Cl1ii2.9500
C18···C6iii3.484 (3)H22···C153.0600
C18···C7iii3.439 (3)H22···C163.0700
C19···C5iii3.504 (3)H23···N2vi2.8900
C19···C4iii3.543 (3)H24···Cl1viii2.9600
C21···C283.313 (3)H24···C5ix2.9400
C22···C163.275 (3)H24···H5ix2.5000
C24···Cl1viii3.563 (2)H25···Cl2v3.1100
C26···C273.173 (3)H26···C133.0100
C27···C263.173 (3)H26···C273.0300
C28···C213.313 (3)H26···Cl1iii3.0800
C3···H10Cvii3.0400H28B···C10vii3.0300
C5···H24ix2.9400H28C···C212.7800
C10···H28Bvii3.0300H28C···C223.0000
C11—O2—C12118.02 (17)C22—C23—C24120.0 (2)
C1—N1—C9117.56 (16)C23—C24—C25119.9 (2)
C12—N2—C20116.71 (17)C24—C25—C26120.3 (2)
Cl1—C1—N1116.13 (15)C21—C26—C25120.7 (2)
Cl1—C1—C2117.06 (16)O1—C27—C13120.6 (2)
N1—C1—C2126.8 (2)O1—C27—C28122.5 (2)
C1—C2—C3115.30 (18)C13—C27—C28116.8 (2)
C1—C2—C11120.44 (18)C2—C3—H3119.00
C3—C2—C11124.26 (17)C4—C3—H3119.00
C2—C3—C4121.56 (17)C4—C5—H5120.00
C3—C4—C5123.17 (18)C6—C5—H5120.00
C3—C4—C9117.67 (19)C5—C6—H6120.00
C5—C4—C9119.16 (19)C7—C6—H6120.00
C4—C5—C6120.2 (2)C6—C7—H7119.00
C5—C6—C7120.0 (3)C8—C7—H7119.00
C6—C7—C8122.8 (2)C8—C10—H10A109.00
C7—C8—C9117.67 (19)C8—C10—H10B109.00
C7—C8—C10122.6 (2)C8—C10—H10C109.00
C9—C8—C10119.8 (2)H10A—C10—H10B110.00
N1—C9—C4121.05 (18)H10A—C10—H10C109.00
N1—C9—C8118.75 (18)H10B—C10—H10C109.00
C4—C9—C8120.2 (2)O2—C11—H11A110.00
O2—C11—C2106.18 (17)O2—C11—H11B110.00
O2—C12—N2119.90 (17)C2—C11—H11A111.00
O2—C12—C13114.06 (18)C2—C11—H11B111.00
N2—C12—C13126.01 (19)H11A—C11—H11B109.00
C12—C13—C14117.91 (19)C15—C16—H16120.00
C12—C13—C27118.15 (17)C17—C16—H16120.00
C14—C13—C27123.84 (17)C17—C18—H18120.00
C13—C14—C15118.45 (17)C19—C18—H18120.00
C13—C14—C21120.10 (19)C18—C19—H19119.00
C15—C14—C21121.44 (17)C20—C19—H19119.00
C14—C15—C16123.51 (17)C21—C22—H22120.00
C14—C15—C20117.99 (18)C23—C22—H22120.00
C16—C15—C20118.50 (19)C22—C23—H23120.00
C15—C16—C17120.23 (18)C24—C23—H23120.00
Cl2—C17—C16120.35 (16)C23—C24—H24120.00
Cl2—C17—C18118.4 (2)C25—C24—H24120.00
C16—C17—C18121.3 (2)C24—C25—H25120.00
C17—C18—C19119.7 (3)C26—C25—H25120.00
C18—C19—C20121.1 (2)C21—C26—H26120.00
N2—C20—C15122.68 (19)C25—C26—H26120.00
N2—C20—C19118.18 (18)C27—C28—H28A110.00
C15—C20—C19119.14 (19)C27—C28—H28B109.00
C14—C21—C22121.01 (18)C27—C28—H28C109.00
C14—C21—C26120.45 (17)H28A—C28—H28B109.00
C22—C21—C26118.49 (18)H28A—C28—H28C109.00
C21—C22—C23120.7 (2)H28B—C28—H28C109.00
C12—O2—C11—C2177.13 (15)N2—C12—C13—C27171.72 (18)
C11—O2—C12—N21.1 (3)C12—C13—C14—C150.5 (3)
C11—O2—C12—C13179.27 (16)C12—C13—C14—C21179.35 (17)
C9—N1—C1—Cl1178.38 (14)C27—C13—C14—C15−175.59 (18)
C9—N1—C1—C2−0.4 (3)C27—C13—C14—C213.2 (3)
C1—N1—C9—C4−2.0 (3)C12—C13—C27—O169.7 (3)
C1—N1—C9—C8179.39 (18)C12—C13—C27—C28−107.3 (2)
C20—N2—C12—O2−178.21 (16)C14—C13—C27—O1−114.2 (2)
C20—N2—C12—C133.9 (3)C14—C13—C27—C2868.9 (3)
C12—N2—C20—C150.8 (3)C13—C14—C15—C16−176.10 (18)
C12—N2—C20—C19−179.37 (18)C13—C14—C15—C203.5 (3)
Cl1—C1—C2—C3−176.91 (14)C21—C14—C15—C165.1 (3)
Cl1—C1—C2—C113.7 (2)C21—C14—C15—C20−175.27 (17)
N1—C1—C2—C31.9 (3)C13—C14—C21—C22−115.6 (2)
N1—C1—C2—C11−177.46 (18)C13—C14—C21—C2661.7 (3)
C1—C2—C3—C4−0.9 (3)C15—C14—C21—C2263.2 (3)
C11—C2—C3—C4178.43 (18)C15—C14—C21—C26−119.5 (2)
C1—C2—C11—O2172.29 (16)C14—C15—C16—C17−177.72 (19)
C3—C2—C11—O2−7.0 (2)C20—C15—C16—C172.7 (3)
C2—C3—C4—C5179.57 (19)C14—C15—C20—N2−4.4 (3)
C2—C3—C4—C9−1.3 (3)C14—C15—C20—C19175.73 (18)
C3—C4—C5—C6178.91 (19)C16—C15—C20—N2175.24 (18)
C9—C4—C5—C6−0.2 (3)C16—C15—C20—C19−4.6 (3)
C3—C4—C9—N12.8 (3)C15—C16—C17—Cl2−178.09 (15)
C3—C4—C9—C8−178.59 (18)C15—C16—C17—C181.1 (3)
C5—C4—C9—N1−177.99 (18)Cl2—C17—C18—C19176.30 (17)
C5—C4—C9—C80.6 (3)C16—C17—C18—C19−2.9 (3)
C4—C5—C6—C7−0.5 (3)C17—C18—C19—C200.8 (3)
C5—C6—C7—C81.0 (3)C18—C19—C20—N2−176.95 (19)
C6—C7—C8—C9−0.6 (3)C18—C19—C20—C152.9 (3)
C6—C7—C8—C10179.3 (2)C14—C21—C22—C23176.0 (2)
C7—C8—C9—N1178.44 (18)C26—C21—C22—C23−1.4 (3)
C7—C8—C9—C4−0.2 (3)C14—C21—C26—C25−176.8 (2)
C10—C8—C9—N1−1.5 (3)C22—C21—C26—C250.6 (3)
C10—C8—C9—C4179.92 (19)C21—C22—C23—C241.0 (3)
O2—C12—C13—C14177.38 (17)C22—C23—C24—C250.2 (4)
O2—C12—C13—C27−6.3 (2)C23—C24—C25—C26−1.1 (4)
N2—C12—C13—C14−4.6 (3)C24—C25—C26—C210.7 (3)
  6 in total

1.  Design and synthesis of Pfmrk inhibitors as potential antimalarial agents.

Authors:  Z Xiao; N C Waters; C L Woodard; Z Li; P K Li
Journal:  Bioorg Med Chem Lett       Date:  2001-11-05       Impact factor: 2.823

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  3-Aryl-2-quinolone derivatives: synthesis and characterization of in vitro and in vivo antitumor effects with emphasis on a new therapeutical target connected with cell migration.

Authors:  Benoît Joseph; Francis Darro; Aurélie Béhard; Brigitte Lesur; Françoise Collignon; Christine Decaestecker; Armand Frydman; Gérald Guillaumet; Robert Kiss
Journal:  J Med Chem       Date:  2002-06-06       Impact factor: 7.446

4.  1-{6-Chloro-2-[(2-chloro-3-quinol-yl)meth-oxy]-4-phenyl-3-quinol-yl}ethan-1-one.

Authors:  F Nawaz Khan; S Mohana Roopan; Rajesh Kumar; Venkatesha R Hathwar; Mehmet Akkurt
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-09

5.  Ethyl 6-chloro-2-[(2-chloro-7,8-dimethyl-quinolin-3-yl)meth-oxy]-4-phenyl-quinoline-3-carboxyl-ate.

Authors:  F Nawaz Khan; S Mohana Roopan; Venkatesha R Hathwar; Mehmet Akkurt
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-27

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  6 in total
  1 in total

1.  Crystal structure, DFT study and Hirshfeld surface analysis of ethyl 6-chloro-2-eth-oxy-quinoline-4-carboxyl-ate.

Authors:  Younos Bouzian; Khalid Karrouchi; El Hassane Anouar; Rachid Bouhfid; Suhana Arshad; El Mokhtar Essassi
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-05-31
  1 in total

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