Literature DB >> 21580187

1-(6-Chloro-2-methyl-4-phenyl-quinolin-3-yl)-3-(3-methoxy-phen-yl)prop-2-en-1-one.

Wan-Sin Loh, Hoong-Kun Fun, S Sarveswari, V Vijayakumar, B Palakshi Reddy.

Abstract

In the title compound, C(26)H(20)ClNO(2), the quinoline ring system is approximately planar with a maximum deviation of 0.028 (2) Å and forms a dihedral angle of 73.84 (5)° with the phenyl ring. Two neighbouring mol-ecules are arranged into a centrosymmetric dimer through a pair of inter-molecular C-H⋯Cl inter-actions. A pair of inter-molecular C-H⋯O hydrogen bonds link two methoxy-phenyl groups into another centrosymmetric dimer, generating an R(2) (2)(8) ring motif. The structure is further stabilized by C-H⋯π inter-actions.

Entities: Chemical Disease Gene

Year: 2009 PMID： 21580187 PMCID： PMC2979994 DOI： 10.1107/S1600536809052179

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

Related literature

For background to and the biological activity of quinolines, see: Michael (1997 ▶); Markees et al. (1970 ▶); Kalluraya & Sreenivasa (1998 ▶); Chen et al. (2001 ▶). For the biological activity of chalcones, see: Dimmock et al. (1999 ▶); Zi & Simoneau (2005 ▶). For related structures, see: Fun et al. (2009 ▶); Loh et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C26H20ClNO2 M = 413.88 Monoclinic, a = 15.6338 (2) Å b = 14.0408 (2) Å c = 10.0321 (1) Å β = 108.462 (1)° V = 2088.82 (5) Å3 Z = 4 Mo Kα radiation μ = 0.21 mm−1 T = 100 K 0.33 × 0.25 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.936, T max = 0.967 51550 measured reflections 6303 independent reflections 5132 reflections with I > 2σ(I) R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.112 S = 1.05 6303 reflections 273 parameters H-atom parameters constrained Δρmax = 0.38 e Å−3 Δρmin = −0.41 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052179/is2501sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052179/is2501Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₆H₂₀ClNO₂	F(000) = 864
M_r = 413.88	D_x = 1.316 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9882 reflections
a = 15.6338 (2) Å	θ = 2.6–30.3°
b = 14.0408 (2) Å	µ = 0.21 mm⁻¹
c = 10.0321 (1) Å	T = 100 K
β = 108.462 (1)°	Block, colourless
V = 2088.82 (5) Å³	0.33 × 0.25 × 0.17 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6303 independent reflections
Radiation source: fine-focus sealed tube	5132 reflections with I > 2σ(I)
graphite	R_int = 0.042
φ and ω scans	θ_max = 30.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −22→22
T_min = 0.936, T_max = 0.967	k = −19→19
51550 measured reflections	l = −14→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0521P)² + 0.7676P] where P = (F_o² + 2F_c²)/3
6303 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

	x	y	z	U_iso*/U_eq
Cl1	0.33917 (2)	0.33164 (3)	0.58574 (4)	0.03525 (10)
O1	0.89366 (6)	0.37834 (7)	0.92588 (10)	0.0275 (2)
O2	0.99503 (6)	0.88427 (6)	1.10271 (9)	0.02503 (19)
N1	0.69406 (7)	0.37222 (7)	0.50187 (10)	0.0202 (2)
C1	0.76533 (8)	0.39716 (8)	0.60758 (12)	0.0194 (2)
C2	0.61229 (8)	0.36683 (8)	0.52489 (12)	0.0186 (2)
C3	0.53676 (9)	0.33562 (9)	0.41238 (13)	0.0232 (2)
H3A	0.5437	0.3220	0.3257	0.028*
C4	0.45373 (9)	0.32536 (9)	0.42991 (13)	0.0245 (3)
H4A	0.4046	0.3044	0.3560	0.029*
C5	0.44385 (8)	0.34703 (10)	0.56185 (13)	0.0230 (2)
C6	0.51471 (8)	0.37833 (9)	0.67275 (12)	0.0208 (2)
H6A	0.5063	0.3926	0.7583	0.025*
C7	0.60098 (8)	0.38886 (8)	0.65627 (11)	0.0175 (2)
C8	0.67867 (8)	0.41709 (8)	0.76909 (11)	0.0170 (2)
C9	0.76028 (7)	0.41997 (8)	0.74412 (12)	0.0174 (2)
C10	0.84595 (8)	0.44340 (9)	0.86210 (12)	0.0195 (2)
C11	0.87075 (8)	0.54318 (9)	0.89574 (13)	0.0217 (2)
H11A	0.9200	0.5564	0.9744	0.026*
C12	0.82630 (8)	0.61647 (9)	0.81913 (13)	0.0204 (2)
H12A	0.7752	0.6020	0.7441	0.024*
C13	0.85050 (7)	0.71727 (9)	0.84237 (12)	0.0191 (2)
C14	0.91311 (8)	0.74920 (9)	0.96894 (12)	0.0196 (2)
H14A	0.9381	0.7067	1.0420	0.024*
C15	0.93706 (8)	0.84453 (9)	0.98366 (12)	0.0198 (2)
C16	0.90136 (8)	0.90856 (9)	0.87281 (13)	0.0226 (2)
H16A	0.9193	0.9720	0.8824	0.027*
C17	0.83926 (8)	0.87700 (9)	0.74883 (13)	0.0227 (2)
H17A	0.8152	0.9195	0.6753	0.027*
C18	0.81280 (8)	0.78194 (9)	0.73403 (13)	0.0214 (2)
H18A	0.7699	0.7614	0.6517	0.026*
C19	0.67020 (7)	0.43834 (9)	0.91020 (11)	0.0177 (2)
C20	0.70262 (9)	0.37333 (9)	1.01947 (13)	0.0233 (2)
H20A	0.7325	0.3187	1.0058	0.028*
C21	0.69045 (9)	0.38998 (10)	1.14923 (13)	0.0269 (3)
H21A	0.7115	0.3461	1.2217	0.032*
C22	0.64704 (9)	0.47190 (10)	1.17049 (13)	0.0260 (3)
H22A	0.6389	0.4829	1.2571	0.031*
C23	0.61572 (9)	0.53749 (10)	1.06250 (13)	0.0257 (3)
H23A	0.5872	0.5928	1.0772	0.031*
C24	0.62681 (8)	0.52078 (9)	0.93238 (12)	0.0221 (2)
H24A	0.6053	0.5646	0.8600	0.027*
C25	0.85421 (9)	0.40069 (11)	0.57958 (14)	0.0269 (3)
H25A	0.8444	0.3918	0.4810	0.040*
H25B	0.8928	0.3511	0.6316	0.040*
H25C	0.8822	0.4614	0.6083	0.040*
C26	1.04176 (9)	0.82146 (10)	1.21483 (13)	0.0257 (3)
H26A	1.0808	0.8579	1.2908	0.038*
H26B	1.0769	0.7769	1.1815	0.038*
H26C	0.9988	0.7875	1.2472	0.038*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01933 (15)	0.0596 (2)	0.02639 (17)	−0.01311 (14)	0.00657 (12)	−0.01568 (15)
O1	0.0238 (4)	0.0259 (5)	0.0278 (5)	0.0019 (4)	0.0009 (4)	0.0005 (4)
O2	0.0280 (5)	0.0226 (4)	0.0205 (4)	−0.0053 (3)	0.0019 (4)	−0.0048 (3)
N1	0.0225 (5)	0.0224 (5)	0.0164 (4)	−0.0023 (4)	0.0071 (4)	−0.0014 (4)
C1	0.0212 (5)	0.0193 (5)	0.0189 (5)	−0.0015 (4)	0.0079 (4)	0.0005 (4)
C2	0.0210 (5)	0.0197 (5)	0.0143 (5)	−0.0027 (4)	0.0047 (4)	−0.0011 (4)
C3	0.0262 (6)	0.0283 (6)	0.0141 (5)	−0.0031 (5)	0.0050 (4)	−0.0037 (4)
C4	0.0238 (6)	0.0308 (7)	0.0156 (5)	−0.0056 (5)	0.0015 (4)	−0.0043 (5)
C5	0.0179 (5)	0.0307 (7)	0.0192 (5)	−0.0043 (4)	0.0042 (4)	−0.0045 (5)
C6	0.0197 (5)	0.0263 (6)	0.0157 (5)	−0.0039 (4)	0.0046 (4)	−0.0050 (4)
C7	0.0189 (5)	0.0187 (5)	0.0139 (5)	−0.0022 (4)	0.0038 (4)	−0.0014 (4)
C8	0.0190 (5)	0.0170 (5)	0.0140 (5)	−0.0016 (4)	0.0036 (4)	−0.0008 (4)
C9	0.0177 (5)	0.0165 (5)	0.0172 (5)	−0.0019 (4)	0.0045 (4)	−0.0005 (4)
C10	0.0167 (5)	0.0230 (6)	0.0182 (5)	−0.0017 (4)	0.0046 (4)	−0.0018 (4)
C11	0.0166 (5)	0.0241 (6)	0.0220 (6)	−0.0034 (4)	0.0026 (4)	−0.0044 (5)
C12	0.0169 (5)	0.0238 (6)	0.0202 (5)	−0.0043 (4)	0.0054 (4)	−0.0043 (4)
C13	0.0155 (5)	0.0223 (6)	0.0199 (5)	−0.0024 (4)	0.0060 (4)	−0.0034 (4)
C14	0.0181 (5)	0.0221 (6)	0.0183 (5)	−0.0025 (4)	0.0053 (4)	−0.0018 (4)
C15	0.0174 (5)	0.0231 (6)	0.0189 (5)	−0.0030 (4)	0.0057 (4)	−0.0055 (4)
C16	0.0235 (6)	0.0193 (6)	0.0254 (6)	−0.0012 (4)	0.0083 (5)	−0.0026 (5)
C17	0.0213 (5)	0.0241 (6)	0.0224 (6)	0.0009 (4)	0.0065 (5)	0.0004 (5)
C18	0.0173 (5)	0.0256 (6)	0.0199 (5)	−0.0007 (4)	0.0040 (4)	−0.0033 (4)
C19	0.0157 (5)	0.0229 (6)	0.0134 (5)	−0.0045 (4)	0.0029 (4)	−0.0025 (4)
C20	0.0273 (6)	0.0230 (6)	0.0187 (5)	−0.0007 (5)	0.0059 (5)	0.0003 (4)
C21	0.0320 (7)	0.0307 (7)	0.0169 (5)	−0.0034 (5)	0.0062 (5)	0.0030 (5)
C22	0.0281 (6)	0.0350 (7)	0.0160 (5)	−0.0076 (5)	0.0086 (5)	−0.0051 (5)
C23	0.0262 (6)	0.0297 (7)	0.0217 (6)	0.0005 (5)	0.0084 (5)	−0.0056 (5)
C24	0.0226 (5)	0.0257 (6)	0.0168 (5)	0.0007 (4)	0.0042 (4)	−0.0011 (4)
C25	0.0232 (6)	0.0355 (7)	0.0248 (6)	−0.0028 (5)	0.0115 (5)	−0.0004 (5)
C26	0.0249 (6)	0.0303 (7)	0.0192 (6)	−0.0043 (5)	0.0034 (5)	−0.0038 (5)

Cl1—C5	1.7410 (12)	C13—C14	1.4087 (16)
O1—C10	1.2239 (15)	C14—C15	1.3852 (17)
O2—C15	1.3687 (14)	C14—H14A	0.9300
O2—C26	1.4340 (16)	C15—C16	1.4012 (18)
N1—C1	1.3192 (15)	C16—C17	1.3860 (17)
N1—C2	1.3713 (15)	C16—H16A	0.9300
C1—C9	1.4331 (16)	C17—C18	1.3913 (18)
C1—C25	1.5030 (16)	C17—H17A	0.9300
C2—C7	1.4184 (15)	C18—H18A	0.9300
C2—C3	1.4200 (16)	C19—C20	1.3927 (17)
C3—C4	1.3717 (18)	C19—C24	1.3947 (17)
C3—H3A	0.9300	C20—C21	1.3938 (17)
C4—C5	1.4135 (17)	C20—H20A	0.9300
C4—H4A	0.9300	C21—C22	1.386 (2)
C5—C6	1.3703 (16)	C21—H21A	0.9300
C6—C7	1.4176 (16)	C22—C23	1.3876 (19)
C6—H6A	0.9300	C22—H22A	0.9300
C7—C8	1.4291 (15)	C23—C24	1.3901 (17)
C8—C9	1.3765 (15)	C23—H23A	0.9300
C8—C19	1.4931 (15)	C24—H24A	0.9300
C9—C10	1.5163 (16)	C25—H25A	0.9600
C10—C11	1.4643 (17)	C25—H25B	0.9600
C11—C12	1.3395 (17)	C25—H25C	0.9600
C11—H11A	0.9300	C26—H26A	0.9600
C12—C13	1.4644 (17)	C26—H26B	0.9600
C12—H12A	0.9300	C26—H26C	0.9600
C13—C18	1.3956 (17)

C15—O2—C26	117.77 (10)	C13—C14—H14A	120.3
C1—N1—C2	118.32 (10)	O2—C15—C14	124.67 (11)
N1—C1—C9	122.65 (10)	O2—C15—C16	114.72 (11)
N1—C1—C25	117.00 (10)	C14—C15—C16	120.61 (11)
C9—C1—C25	120.35 (11)	C17—C16—C15	119.79 (11)
N1—C2—C7	122.80 (10)	C17—C16—H16A	120.1
N1—C2—C3	117.91 (10)	C15—C16—H16A	120.1
C7—C2—C3	119.27 (11)	C16—C17—C18	120.17 (12)
C4—C3—C2	120.87 (11)	C16—C17—H17A	119.9
C4—C3—H3A	119.6	C18—C17—H17A	119.9
C2—C3—H3A	119.6	C17—C18—C13	120.21 (11)
C3—C4—C5	119.07 (11)	C17—C18—H18A	119.9
C3—C4—H4A	120.5	C13—C18—H18A	119.9
C5—C4—H4A	120.5	C20—C19—C24	119.51 (11)
C6—C5—C4	121.97 (11)	C20—C19—C8	119.73 (11)
C6—C5—Cl1	118.79 (9)	C24—C19—C8	120.72 (10)
C4—C5—Cl1	119.24 (9)	C19—C20—C21	120.13 (12)
C5—C6—C7	119.55 (11)	C19—C20—H20A	119.9
C5—C6—H6A	120.2	C21—C20—H20A	119.9
C7—C6—H6A	120.2	C22—C21—C20	120.08 (12)
C6—C7—C2	119.26 (10)	C22—C21—H21A	120.0
C6—C7—C8	122.54 (10)	C20—C21—H21A	120.0
C2—C7—C8	118.14 (10)	C21—C22—C23	119.98 (11)
C9—C8—C7	117.92 (10)	C21—C22—H22A	120.0
C9—C8—C19	122.16 (10)	C23—C22—H22A	120.0
C7—C8—C19	119.86 (10)	C22—C23—C24	120.20 (12)
C8—C9—C1	120.15 (10)	C22—C23—H23A	119.9
C8—C9—C10	120.32 (10)	C24—C23—H23A	119.9
C1—C9—C10	119.48 (10)	C23—C24—C19	120.10 (12)
O1—C10—C11	121.37 (11)	C23—C24—H24A	120.0
O1—C10—C9	119.18 (11)	C19—C24—H24A	120.0
C11—C10—C9	119.44 (10)	C1—C25—H25A	109.5
C12—C11—C10	123.47 (11)	C1—C25—H25B	109.5
C12—C11—H11A	118.3	H25A—C25—H25B	109.5
C10—C11—H11A	118.3	C1—C25—H25C	109.5
C11—C12—C13	126.17 (11)	H25A—C25—H25C	109.5
C11—C12—H12A	116.9	H25B—C25—H25C	109.5
C13—C12—H12A	116.9	O2—C26—H26A	109.5
C18—C13—C14	119.77 (11)	O2—C26—H26B	109.5
C18—C13—C12	118.73 (11)	H26A—C26—H26B	109.5
C14—C13—C12	121.45 (11)	O2—C26—H26C	109.5
C15—C14—C13	119.40 (11)	H26A—C26—H26C	109.5
C15—C14—H14A	120.3	H26B—C26—H26C	109.5

C2—N1—C1—C9	−0.89 (17)	C8—C9—C10—C11	−84.74 (14)
C2—N1—C1—C25	178.93 (11)	C1—C9—C10—C11	97.70 (13)
C1—N1—C2—C7	1.39 (17)	O1—C10—C11—C12	172.29 (12)
C1—N1—C2—C3	−177.10 (11)	C9—C10—C11—C12	−6.60 (18)
N1—C2—C3—C4	177.64 (12)	C10—C11—C12—C13	−176.37 (11)
C7—C2—C3—C4	−0.90 (19)	C11—C12—C13—C18	163.13 (12)
C2—C3—C4—C5	0.5 (2)	C11—C12—C13—C14	−14.47 (18)
C3—C4—C5—C6	0.2 (2)	C18—C13—C14—C15	−0.56 (17)
C3—C4—C5—Cl1	−178.61 (10)	C12—C13—C14—C15	177.02 (11)
C4—C5—C6—C7	−0.5 (2)	C26—O2—C15—C14	7.01 (17)
Cl1—C5—C6—C7	178.35 (10)	C26—O2—C15—C16	−173.30 (11)
C5—C6—C7—C2	0.07 (18)	C13—C14—C15—O2	178.05 (11)
C5—C6—C7—C8	−177.16 (12)	C13—C14—C15—C16	−1.62 (17)
N1—C2—C7—C6	−177.85 (11)	O2—C15—C16—C17	−177.59 (11)
C3—C2—C7—C6	0.61 (17)	C14—C15—C16—C17	2.11 (18)
N1—C2—C7—C8	−0.50 (17)	C15—C16—C17—C18	−0.38 (18)
C3—C2—C7—C8	177.97 (11)	C16—C17—C18—C13	−1.81 (18)
C6—C7—C8—C9	176.38 (11)	C14—C13—C18—C17	2.28 (17)
C2—C7—C8—C9	−0.88 (16)	C12—C13—C18—C17	−175.37 (11)
C6—C7—C8—C19	−1.07 (17)	C9—C8—C19—C20	−71.87 (15)
C2—C7—C8—C19	−178.33 (10)	C7—C8—C19—C20	105.47 (13)
C7—C8—C9—C1	1.36 (16)	C9—C8—C19—C24	110.80 (13)
C19—C8—C9—C1	178.75 (11)	C7—C8—C19—C24	−71.86 (15)
C7—C8—C9—C10	−176.19 (10)	C24—C19—C20—C21	1.01 (18)
C19—C8—C9—C10	1.20 (17)	C8—C19—C20—C21	−176.35 (11)
N1—C1—C9—C8	−0.50 (18)	C19—C20—C21—C22	−0.8 (2)
C25—C1—C9—C8	179.69 (11)	C20—C21—C22—C23	0.0 (2)
N1—C1—C9—C10	177.07 (11)	C21—C22—C23—C24	0.7 (2)
C25—C1—C9—C10	−2.74 (17)	C22—C23—C24—C19	−0.54 (19)
C8—C9—C10—O1	96.34 (14)	C20—C19—C24—C23	−0.33 (18)
C1—C9—C10—O1	−81.22 (15)	C8—C19—C24—C23	177.01 (11)

Cg1 and Cg2 are the centroids of the C13–C18 and C19–C24 rings, resepctively.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2ⁱ	0.93	2.40	3.3005 (15)	163
C18—H18A···Cl1ⁱⁱ	0.93	2.78	3.6948 (13)	169
C26—H26B···O1ⁱⁱⁱ	0.96	2.54	3.4329 (17)	155
C26—H26C···Cg1^iv	0.96	2.88	3.8412 (15)	177
C17—H17A···Cg2^v	0.93	2.97	3.7592 (14)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2ⁱ	0.93	2.40	3.3005 (15)	163
C18—H18A⋯Cl1ⁱⁱ	0.93	2.78	3.6948 (13)	169
C26—H26B⋯O1ⁱⁱⁱ	0.96	2.54	3.4329 (17)	155
C26—H26C⋯Cg1^iv	0.96	2.88	3.8412 (15)	177
C17—H17A⋯Cg2^v	0.93	2.97	3.7592 (14)	144

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 and Cg2 are the centroids of the C13–C18 and C19–C24 rings, respectively.

9 in total

Review 1. Bioactivities of chalcones.

Authors: J R Dimmock; D W Elias; M A Beazely; N M Kandepu
Journal: Curr Med Chem Date: 1999-12 Impact factor: 4.530

2. A short history of SHELX.

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

3. Antiprotozoal 4-aryloxy-2-aminoquinolines and related compounds.

Authors: D G Markees; V C Dewey; G W Kidder
Journal: J Med Chem Date: 1970-03 Impact factor: 7.446

4. Flavokawain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice.

Authors: Xiaolin Zi; Anne R Simoneau
Journal: Cancer Res Date: 2005-04-15 Impact factor: 12.701

5. Synthesis and antibacterial evaluation of certain quinolone derivatives.

Authors: Y L Chen; K C Fang; J Y Sheu; S L Hsu; C C Tzeng
Journal: J Med Chem Date: 2001-07-05 Impact factor: 7.446

6. 3-Acetyl-6-chloro-2-methyl-4-phenyl-quinolinium hydrogen sulfate.

Authors: Wan-Sin Loh; Hoong-Kun Fun; S Sarveswari; V Vijayakumar; B Palakshi Reddy
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-11-21

7. 1-(6-Chloro-2-methyl-4-phenyl-3-quinol-yl)ethanone.

Authors: Hoong-Kun Fun; Wan-Sin Loh; S Sarveswari; V Vijayakumar; B Palakshi Reddy
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-10-10

8. Synthesis and pharmacological properties of some quinoline derivatives.

Authors: B Kalluraya; S Sreenivasa
Journal: Farmaco Date: 1998-06-30

9. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20