Literature DB >> 21577604

3-(2-Chloro-ethyl)-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium 2,4,6-trinitro-phenolate.

Jerry P Jasinski, Ray J Butcher, Q N M Hakim Al-Arique, H S Yathirajan, B Narayana.   

Abstract

In the cation of the title salt, C(11)H(12)ClN(2)O(+)·C(6)H(2)N(3)O(7) (-), the chloro-ethyl side chain is in a syn conformation, nearly orthogonal to the pyrimidine ring, with a dihedral angle of 78.9 (6)° between the plane of the chloro-ethyl chain and the pyrimidine ring. The dihedral angle between the fused rings is 4.3 (3)°. In the picrate anion, the benzene mean plane makes dihedral angles of 26.7 (1), 33.6 (2) and 5.3 (6)° with the two o-NO(2) groups and the p-NO(2) group, respectively. Extensive hydrogen-bond inter-actions occur between the cation-anion pair which help to establish the crystal packing. A three-center O⋯(H,H)-(N,C) acceptor hydrogen bond is observed between the phenolate O atom of the picrate anion and the amine and methyl groups of the cation. An N-H⋯(O,O) bifurcated hydrogen bond is observed between the amine group and two O atoms from the phenolate and o-NO(2) groups.

Entities:  

Year:  2009        PMID： 21577604      PMCID： PMC2970075          DOI： 10.1107/S1600536809032693

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


Related literature

For related structures, see: Blaton et al. (1995 ▶); Chen & He (2006 ▶); Peeters et al. (1993 ▶). For general background, see: Baraldi et al. (2002 ▶); Gabbert & Giannini (1997 ▶); Jasinski et al. (2009 ▶); White et al. (2004 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶) and for the program Mogul, see: Bruno et al. (2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C11H12ClN2O+·C6H2N3O7 − M = 451.78 Monoclinic, a = 7.2718 (5) Å b = 12.8159 (9) Å c = 19.940 (3) Å β = 97.642 (9)° V = 1841.8 (3) Å3 Z = 4 Cu Kα radiation μ = 2.41 mm−1 T = 110 K 0.44 × 0.37 × 0.23 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector Absorption correction: multi-scan (; Oxford Diffraction, 2007 ▶) T min = 0.309, T max = 0.575 6948 measured reflections 3616 independent reflections 3198 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.097 S = 1.03 3616 reflections 281 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.29 e Å−3 Data collection: CrysAlis Pro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032693/is2446sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032693/is2446Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C11H12ClN2O+·C6H2N3O7−F(000) = 928
Mr = 451.78Dx = 1.629 Mg m−3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ynCell parameters from 4324 reflections
a = 7.2718 (5) Åθ = 4.1–74.1°
b = 12.8159 (9) ŵ = 2.40 mm−1
c = 19.940 (3) ÅT = 110 K
β = 97.642 (9)°Chunk, pale yellow
V = 1841.8 (3) Å30.44 × 0.37 × 0.23 mm
Z = 4
Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector3616 independent reflections
Radiation source: Enhance (Cu) X-ray Source3198 reflections with I > 2σ(I)
graphiteRint = 0.017
Detector resolution: 10.5081 pixels mm-1θmax = 74.0°, θmin = 4.1°
ω scansh = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)k = −15→9
Tmin = 0.309, Tmax = 0.575l = −23→24
6948 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.063P)2 + 0.629P] where P = (Fo2 + 2Fc2)/3
3616 reflections(Δ/σ)max < 0.001
281 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
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.
xyzUiso*/Ueq
Cl1A0.86173 (5)0.88220 (3)0.687448 (19)0.02115 (12)
O1A0.51748 (16)0.63234 (9)0.76768 (5)0.0210 (2)
N1A0.37082 (17)0.50513 (9)0.69885 (6)0.0150 (3)
C1A0.5193 (2)0.58121 (11)0.71692 (8)0.0162 (3)
C2A0.6526 (2)0.58732 (11)0.66975 (7)0.0153 (3)
C3A0.6432 (2)0.52080 (11)0.61613 (7)0.0154 (3)
N4A0.50951 (17)0.44532 (10)0.60742 (6)0.0162 (3)
H4AA0.51240.40000.57440.019*
C5A0.3734 (2)0.43685 (11)0.64690 (7)0.0157 (3)
C6A0.2346 (2)0.35986 (12)0.63478 (8)0.0196 (3)
H6AA0.23780.31050.59940.024*
C7A0.0949 (2)0.35698 (13)0.67466 (9)0.0226 (3)
H7AA0.00180.30460.66770.027*
C8A0.0903 (2)0.43233 (13)0.72609 (8)0.0227 (3)
H8AA−0.00950.43280.75240.027*
C9A0.2275 (2)0.50377 (12)0.73803 (8)0.0190 (3)
H9AA0.22540.55320.77340.023*
C10A0.7963 (2)0.67205 (12)0.68363 (8)0.0171 (3)
H10A0.90370.65680.65950.021*
H10B0.84090.67540.73270.021*
C11A0.7098 (2)0.77552 (12)0.65971 (8)0.0187 (3)
H11A0.59040.78440.67780.022*
H11B0.68430.77570.60970.022*
C12A0.7717 (2)0.52487 (13)0.56313 (8)0.0202 (3)
H12A0.90030.51880.58480.030*
H12B0.75540.59140.53880.030*
H12C0.74330.46710.53120.030*
O1B0.57412 (15)0.30604 (8)0.51298 (5)0.0185 (2)
O21B0.81068 (17)0.36265 (9)0.42333 (6)0.0246 (3)
O22B0.75216 (16)0.25511 (9)0.33919 (6)0.0223 (3)
O41B0.88575 (16)−0.10609 (9)0.40701 (6)0.0233 (3)
O42B0.78903 (17)−0.16264 (9)0.49860 (6)0.0248 (3)
O61B0.52961 (16)0.07476 (10)0.64703 (6)0.0250 (3)
O62B0.61759 (18)0.23621 (9)0.64474 (6)0.0257 (3)
N2B0.76693 (17)0.27587 (10)0.40009 (7)0.0174 (3)
N4B0.81817 (17)−0.09140 (10)0.45962 (7)0.0175 (3)
N6B0.59534 (18)0.14919 (11)0.61918 (6)0.0180 (3)
C1B0.6503 (2)0.21995 (11)0.50651 (7)0.0145 (3)
C2B0.7355 (2)0.19261 (12)0.44702 (7)0.0153 (3)
C3B0.7866 (2)0.09381 (12)0.43082 (7)0.0158 (3)
H3BA0.83350.08040.38940.019*
C4B0.76828 (19)0.01382 (12)0.47634 (7)0.0156 (3)
C5B0.70412 (19)0.03312 (12)0.53788 (7)0.0157 (3)
H5BA0.6955−0.02200.56910.019*
C6B0.6534 (2)0.13254 (12)0.55290 (7)0.0151 (3)
U11U22U33U12U13U23
Cl1A0.0225 (2)0.0160 (2)0.0248 (2)−0.00529 (13)0.00290 (15)−0.00297 (14)
O1A0.0287 (6)0.0192 (6)0.0158 (5)−0.0004 (4)0.0054 (4)−0.0034 (4)
N1A0.0175 (6)0.0129 (6)0.0149 (6)0.0017 (5)0.0037 (5)0.0018 (5)
C1A0.0202 (7)0.0121 (7)0.0157 (7)0.0020 (6)0.0006 (6)0.0025 (6)
C2A0.0158 (7)0.0143 (7)0.0154 (7)0.0002 (6)0.0009 (5)0.0019 (5)
C3A0.0154 (7)0.0140 (7)0.0167 (7)0.0020 (5)0.0018 (5)0.0017 (6)
N4A0.0189 (6)0.0144 (6)0.0159 (6)0.0004 (5)0.0044 (5)−0.0028 (5)
C5A0.0187 (7)0.0128 (7)0.0156 (7)0.0032 (6)0.0023 (6)0.0027 (5)
C6A0.0218 (8)0.0136 (7)0.0232 (8)0.0012 (6)0.0023 (6)0.0006 (6)
C7A0.0205 (8)0.0169 (7)0.0303 (9)−0.0027 (6)0.0035 (7)0.0057 (6)
C8A0.0225 (8)0.0234 (8)0.0237 (8)0.0017 (6)0.0089 (6)0.0076 (7)
C9A0.0226 (7)0.0190 (7)0.0165 (7)0.0039 (6)0.0069 (6)0.0048 (6)
C10A0.0176 (7)0.0171 (7)0.0163 (7)−0.0007 (6)0.0010 (6)−0.0011 (6)
C11A0.0180 (7)0.0150 (7)0.0221 (8)−0.0044 (6)−0.0002 (6)−0.0017 (6)
C12A0.0213 (7)0.0221 (8)0.0183 (7)−0.0019 (6)0.0063 (6)−0.0027 (6)
O1B0.0219 (5)0.0163 (5)0.0175 (5)0.0027 (4)0.0037 (4)−0.0018 (4)
O21B0.0309 (6)0.0177 (6)0.0261 (6)−0.0055 (5)0.0071 (5)−0.0003 (5)
O22B0.0257 (6)0.0268 (6)0.0149 (5)0.0026 (5)0.0045 (4)0.0025 (5)
O41B0.0264 (6)0.0222 (6)0.0226 (6)0.0026 (5)0.0085 (5)−0.0070 (5)
O42B0.0296 (6)0.0152 (5)0.0313 (7)0.0001 (5)0.0103 (5)0.0018 (5)
O61B0.0266 (6)0.0304 (7)0.0199 (6)−0.0034 (5)0.0096 (5)0.0024 (5)
O62B0.0412 (7)0.0208 (6)0.0149 (5)0.0088 (5)0.0029 (5)−0.0030 (4)
N2B0.0148 (6)0.0188 (7)0.0190 (6)0.0009 (5)0.0039 (5)0.0017 (5)
N4B0.0141 (6)0.0172 (6)0.0210 (7)−0.0015 (5)0.0018 (5)−0.0039 (5)
N6B0.0177 (6)0.0220 (7)0.0143 (6)0.0041 (5)0.0027 (5)0.0012 (5)
C1B0.0129 (6)0.0157 (7)0.0148 (7)−0.0008 (5)0.0010 (5)−0.0021 (6)
C2B0.0141 (6)0.0178 (7)0.0140 (7)−0.0020 (5)0.0016 (5)0.0011 (6)
C3B0.0131 (7)0.0198 (7)0.0145 (7)−0.0007 (6)0.0025 (5)−0.0026 (6)
C4B0.0138 (7)0.0155 (7)0.0175 (7)−0.0005 (5)0.0019 (5)−0.0036 (6)
C5B0.0125 (7)0.0166 (7)0.0178 (7)−0.0014 (5)0.0011 (5)0.0007 (6)
C6B0.0136 (7)0.0186 (7)0.0133 (7)−0.0003 (5)0.0028 (5)−0.0011 (6)
Cl1A—C11A1.7979 (15)C11A—H11A0.9900
O1A—C1A1.2073 (19)C11A—H11B0.9900
N1A—C5A1.3582 (19)C12A—H12A0.9800
N1A—C9A1.3835 (19)C12A—H12B0.9800
N1A—C1A1.4636 (19)C12A—H12C0.9800
C1A—C2A1.440 (2)O1B—C1B1.2489 (18)
C2A—C3A1.362 (2)O21B—N2B1.2303 (18)
C2A—C10A1.507 (2)O22B—N2B1.2337 (17)
C3A—N4A1.3659 (19)O41B—N4B1.2307 (17)
C3A—C12A1.502 (2)O42B—N4B1.2355 (18)
N4A—C5A1.3485 (19)O61B—N6B1.2317 (18)
N4A—H4AA0.8800O62B—N6B1.2279 (18)
C5A—C6A1.409 (2)N2B—C2B1.4572 (19)
C6A—C7A1.372 (2)N4B—C4B1.4469 (19)
C6A—H6AA0.9500N6B—C6B1.4559 (19)
C7A—C8A1.412 (2)C1B—C6B1.451 (2)
C7A—H7AA0.9500C1B—C2B1.452 (2)
C8A—C9A1.352 (2)C2B—C3B1.370 (2)
C8A—H8AA0.9500C3B—C4B1.387 (2)
C9A—H9AA0.9500C3B—H3BA0.9500
C10A—C11A1.517 (2)C4B—C5B1.392 (2)
C10A—H10A0.9900C5B—C6B1.371 (2)
C10A—H10B0.9900C5B—H5BA0.9500
C5A—N1A—C9A120.69 (13)Cl1A—C11A—H11A109.5
C5A—N1A—C1A122.17 (12)C10A—C11A—H11B109.5
C9A—N1A—C1A117.12 (13)Cl1A—C11A—H11B109.5
O1A—C1A—C2A126.96 (14)H11A—C11A—H11B108.1
O1A—C1A—N1A118.57 (14)C3A—C12A—H12A109.5
C2A—C1A—N1A114.47 (13)C3A—C12A—H12B109.5
C3A—C2A—C1A120.70 (14)H12A—C12A—H12B109.5
C3A—C2A—C10A123.83 (14)C3A—C12A—H12C109.5
C1A—C2A—C10A115.46 (13)H12A—C12A—H12C109.5
C2A—C3A—N4A120.25 (13)H12B—C12A—H12C109.5
C2A—C3A—C12A124.01 (14)O21B—N2B—O22B123.36 (13)
N4A—C3A—C12A115.73 (13)O21B—N2B—C2B118.35 (13)
C5A—N4A—C3A123.23 (13)O22B—N2B—C2B118.27 (13)
C5A—N4A—H4AA118.4O41B—N4B—O42B122.99 (13)
C3A—N4A—H4AA118.4O41B—N4B—C4B118.67 (13)
N4A—C5A—N1A118.62 (13)O42B—N4B—C4B118.33 (13)
N4A—C5A—C6A121.39 (14)O62B—N6B—O61B123.63 (13)
N1A—C5A—C6A119.99 (14)O62B—N6B—C6B118.15 (13)
C7A—C6A—C5A119.23 (15)O61B—N6B—C6B118.20 (13)
C7A—C6A—H6AA120.4O1B—C1B—C6B125.86 (14)
C5A—C6A—H6AA120.4O1B—C1B—C2B122.74 (13)
C6A—C7A—C8A119.56 (15)C6B—C1B—C2B111.23 (13)
C6A—C7A—H7AA120.2C3B—C2B—C1B125.03 (13)
C8A—C7A—H7AA120.2C3B—C2B—N2B117.04 (13)
C9A—C8A—C7A120.20 (15)C1B—C2B—N2B117.92 (13)
C9A—C8A—H8AA119.9C2B—C3B—C4B118.42 (14)
C7A—C8A—H8AA119.9C2B—C3B—H3BA120.8
C8A—C9A—N1A120.20 (15)C4B—C3B—H3BA120.8
C8A—C9A—H9AA119.9C3B—C4B—C5B121.21 (14)
N1A—C9A—H9AA119.9C3B—C4B—N4B119.28 (13)
C2A—C10A—C11A108.90 (12)C5B—C4B—N4B119.51 (13)
C2A—C10A—H10A109.9C6B—C5B—C4B119.29 (14)
C11A—C10A—H10A109.9C6B—C5B—H5BA120.4
C2A—C10A—H10B109.9C4B—C5B—H5BA120.4
C11A—C10A—H10B109.9C5B—C6B—C1B124.09 (14)
H10A—C10A—H10B108.3C5B—C6B—N6B116.97 (13)
C10A—C11A—Cl1A110.85 (11)C1B—C6B—N6B118.92 (13)
C10A—C11A—H11A109.5
C5A—N1A—C1A—O1A−172.72 (13)C2A—C10A—C11A—Cl1A170.43 (10)
C9A—N1A—C1A—O1A6.0 (2)O1B—C1B—C2B—C3B−165.97 (15)
C5A—N1A—C1A—C2A8.26 (19)C6B—C1B—C2B—C3B9.5 (2)
C9A—N1A—C1A—C2A−173.04 (12)O1B—C1B—C2B—N2B13.0 (2)
O1A—C1A—C2A—C3A176.59 (15)C6B—C1B—C2B—N2B−171.52 (12)
N1A—C1A—C2A—C3A−4.5 (2)O21B—N2B—C2B—C3B−145.18 (14)
O1A—C1A—C2A—C10A−4.5 (2)O22B—N2B—C2B—C3B33.30 (19)
N1A—C1A—C2A—C10A174.42 (12)O21B—N2B—C2B—C1B35.76 (19)
C1A—C2A—C3A—N4A−1.8 (2)O22B—N2B—C2B—C1B−145.77 (14)
C10A—C2A—C3A—N4A179.40 (13)C1B—C2B—C3B—C4B−4.6 (2)
C1A—C2A—C3A—C12A177.36 (14)N2B—C2B—C3B—C4B176.39 (13)
C10A—C2A—C3A—C12A−1.5 (2)C2B—C3B—C4B—C5B−1.6 (2)
C2A—C3A—N4A—C5A5.2 (2)C2B—C3B—C4B—N4B178.83 (13)
C12A—C3A—N4A—C5A−174.00 (13)O41B—N4B—C4B—C3B4.1 (2)
C3A—N4A—C5A—N1A−1.5 (2)O42B—N4B—C4B—C3B−175.13 (13)
C3A—N4A—C5A—C6A177.89 (14)O41B—N4B—C4B—C5B−175.43 (13)
C9A—N1A—C5A—N4A175.85 (13)O42B—N4B—C4B—C5B5.3 (2)
C1A—N1A—C5A—N4A−5.5 (2)C3B—C4B—C5B—C6B1.8 (2)
C9A—N1A—C5A—C6A−3.5 (2)N4B—C4B—C5B—C6B−178.67 (13)
C1A—N1A—C5A—C6A175.12 (13)C4B—C5B—C6B—C1B4.3 (2)
N4A—C5A—C6A—C7A−177.42 (14)C4B—C5B—C6B—N6B−177.30 (13)
N1A—C5A—C6A—C7A2.0 (2)O1B—C1B—C6B—C5B166.06 (15)
C5A—C6A—C7A—C8A1.3 (2)C2B—C1B—C6B—C5B−9.2 (2)
C6A—C7A—C8A—C9A−3.1 (2)O1B—C1B—C6B—N6B−12.4 (2)
C7A—C8A—C9A—N1A1.6 (2)C2B—C1B—C6B—N6B172.34 (12)
C5A—N1A—C9A—C8A1.8 (2)O62B—N6B—C6B—C5B152.45 (14)
C1A—N1A—C9A—C8A−176.96 (13)O61B—N6B—C6B—C5B−26.3 (2)
C3A—C2A—C10A—C11A100.58 (17)O62B—N6B—C6B—C1B−29.02 (19)
C1A—C2A—C10A—C11A−78.29 (16)O61B—N6B—C6B—C1B152.23 (13)
D—H···AD—HH···AD···AD—H···A
N4A—H4AA···O1B0.881.822.6811 (16)167
N4A—H4AA···O62B0.882.582.8632 (17)100
C5B—H5BA···Cl1Ai0.952.793.6112 (16)146
C7A—H7AA···O1Aii0.952.573.2446 (19)128
C12A—H12C···O1B0.982.413.2477 (19)144
C9A—H9AA···O61Biii0.952.613.2734 (19)127
C12A—H12A···O21Biv0.982.623.340 (2)131
C10A—H10B···O62Bv0.992.543.494 (2)161
C11A—H11A···O22Bvi0.992.523.385 (2)146
C11A—H11B···O42Bvii0.992.563.431 (2)147
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N4A—H4AA⋯O1B0.881.822.6811 (16)167
N4A—H4AA⋯O62B0.882.582.8632 (17)100
C5B—H5BA⋯Cl1Ai0.952.793.6112 (16)146
C7A—H7AA⋯O1Aii0.952.573.2446 (19)128
C12A—H12C⋯O1B0.982.413.2477 (19)144
C9A—H9AA⋯O61Biii0.952.613.2734 (19)127
C12A—H12A⋯O21Biv0.982.623.340 (2)131
C10A—H10B⋯O62Bv0.992.543.494 (2)161
C11A—H11A⋯O22Bvi0.992.523.385 (2)146
C11A—H11B⋯O42Bvii0.992.563.431 (2)147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

  6 in total

1.  Clinical Therapeutic Conference: dopaminergic/serotonergic actions of phencyclidine as a model for schizophreniform psychosis.

Authors:  J F Gabbert; A J Giannini
Journal:  Am J Ther       Date:  1997-04       Impact factor: 2.688

2.  The Cambridge Structural Database: a quarter of a million crystal structures and rising.

Authors:  Frank H Allen
Journal:  Acta Crystallogr B       Date:  2002-05-29

3.  Retrieval of crystallographically-derived molecular geometry information.

Authors:  Ian J Bruno; Jason C Cole; Magnus Kessler; Jie Luo; W D Sam Motherwell; Lucy H Purkis; Barry R Smith; Robin Taylor; Richard I Cooper; Stephanie E Harris; A Guy Orpen
Journal:  J Chem Inf Comput Sci       Date:  2004 Nov-Dec

4.  A short history of SHELX.

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

5.  7-Substituted 5-amino-2-(2-furyl)pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines as A2A adenosine receptor antagonists: a study on the importance of modifications at the side chain on the activity and solubility.

Authors:  Pier Giovanni Baraldi; Barbara Cacciari; Romeo Romagnoli; Giampiero Spalluto; Angela Monopoli; Ennio Ongini; Katia Varani; Pier Andrea Borea
Journal:  J Med Chem       Date:  2002-01-03       Impact factor: 7.446

6.  Synthesis and anticonvulsant evaluation of some new 2-substituted-3-arylpyrido[2,3-d]pyrimidinones.

Authors:  David C White; Thomas D Greenwood; Aaron L Downey; Jeffrey R Bloomquist; James F Wolfe
Journal:  Bioorg Med Chem       Date:  2004-11-01       Impact factor: 3.641
  6 in total

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