Literature DB >> 25553023

Crystal structure of 2-[12-methyl-14-phenyl-10,13,14,16-tetra-aza-tetra-cyclo[7.7.0.0(2,7).0(11,15)]hexa-deca-1(16),2,4,6,9,11(15),12-heptaen-8-yl-idene]propandi-nitrile.

Joel T Mague1, Shaaban K Mohamed2, Mehmet Akkurt3, Hussein M S El-Kashef4, Mustafa R Albayati5.   

Abstract

In the title mol-ecule, C22H12N6, the fused tetracyclic core shows a small lengthwise twist as indicated by the dihedral of 2.7 (2)° between the outer rings. In the crystal, mol-ecules stack along the b-axis direction via offset π-stacking [centroid-centroid distances = 3.5282 (13) and 3.5597 (14) Å] with the stacks weakly associated through C-H⋯N hydrogen bonds. The phenyl ring is rotationally disordered over two orientations with an occupancy ratio of 0.516 (4):0.484 (4).

Entities:  

Keywords:  crystal structure; fused tetracyclic core; hepta­ene; propandi­nitrile; pyrazine scaffold compound

Year:  2014        PMID： 25553023      PMCID： PMC4257392          DOI： 10.1107/S1600536814024167

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


Related literature

For the biological properties of pyrazine scaffold compounds, see: Kaliszan et al. (1985 ▶); Makino et al. (1990 ▶); Emary & Ibrahim (2006 ▶); Silva et al. (2010 ▶); Rusinov et al. (2005 ▶); Johnston & Kau (1993 ▶); Myadaraboina et al. (2010 ▶); Metobo et al. (2006 ▶). For use of pyrazines in industrial chemistry see: Rangnekar & Dhamnaskar, 1990 ▶). For the preparation of the title compound, see: El-Emary & El-Kashef (2013 ▶)

Experimental

Crystal data

C22H12N6 M = 360.38 Monoclinic, a = 35.968 (5) Å b = 4.6483 (6) Å c = 26.596 (3) Å β = 129.6130 (12)° V = 3425.5 (8) Å3 Z = 8 Mo Kα radiation μ = 0.09 mm−1 T = 150 K 0.21 × 0.13 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2014 ▶) T min = 0.77, T max = 0.99 15751 measured reflections 3921 independent reflections 2489 reflections with I > 2σ(I) R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.136 S = 1.03 3921 reflections 249 parameters 1 restraint H-atom parameters constrained Δρmax = 0.31 e Å−3 Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2014 ▶); cell refinement: SAINT (Bruker, 2014 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814024167/su5012sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814024167/su5012Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814024167/su5012Isup3.cml Click here for additional data file. . DOI: 10.1107/S1600536814024167/su5012fig1.tif The mol­ecular structure of the title mol­ecule, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Click here for additional data file. . DOI: 10.1107/S1600536814024167/su5012fig2.tif Portions of two neighboring stacks showing the offset π-stacking and C—H⋯N inter­actions (Table 1) as green and blue dotted line, respectively. Click here for additional data file. b . DOI: 10.1107/S1600536814024167/su5012fig3.tif Crystal packing viewed along the b axis showing stacks of mol­ecules connected by the weak C—H⋯N inter­actions (blue dotted lines; see Table 1 for details). CCDC reference: 1032263 Additional supporting information: crystallographic information; 3D view; checkCIF report
C22H12N6F(000) = 1488
Mr = 360.38Dx = 1.398 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 35.968 (5) ÅCell parameters from 4540 reflections
b = 4.6483 (6) Åθ = 2.3–27.4°
c = 26.596 (3) ŵ = 0.09 mm−1
β = 129.6130 (12)°T = 150 K
V = 3425.5 (8) Å3Column, orange
Z = 80.21 × 0.13 × 0.07 mm
Bruker SMART APEX CCD diffractometer3921 independent reflections
Radiation source: fine-focus sealed tube2489 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 8.3660 pixels mm-1θmax = 27.5°, θmin = 2.0°
φ and ω scansh = −46→46
Absorption correction: multi-scan (SADABS; Bruker, 2014)k = −6→6
Tmin = 0.77, Tmax = 0.99l = −34→34
15751 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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0537P)2 + 1.9123P] where P = (Fo2 + 2Fc2)/3
3921 reflections(Δ/σ)max = 0.001
249 parametersΔρmax = 0.31 e Å−3
1 restraintΔρmin = −0.20 e Å−3
Experimental. The diffraction data were collected in three sets of 400 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 90 sec/frame was used.
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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. The phenyl ring attached to N1 is rotationally disordered over two sites in approximately equal amounts. The components of the disorder were refined as rigid hexagons.
xyzUiso*/UeqOcc. (<1)
N10.69392 (6)0.2255 (4)0.36211 (8)0.0427 (4)
N20.66369 (7)0.0716 (4)0.36798 (9)0.0482 (5)
N30.68329 (6)0.5915 (3)0.28798 (8)0.0385 (4)
N40.58234 (6)0.5174 (4)0.23053 (8)0.0418 (4)
N50.46527 (7)0.6261 (5)0.12918 (10)0.0679 (6)
N60.46809 (7)1.2638 (5)0.01592 (10)0.0657 (6)
C10.74396 (18)0.1886 (11)0.4101 (2)0.0444 (5)0.516 (4)
C20.7750 (3)0.2928 (12)0.4002 (2)0.0565 (14)0.516 (4)
H20.76240.38760.36050.068*0.516 (4)
C30.8246 (2)0.2582 (13)0.4482 (3)0.0568 (13)0.516 (4)
H30.84580.32940.44140.068*0.516 (4)
C40.84309 (16)0.1195 (12)0.5063 (3)0.0611 (7)0.516 (4)
H40.87700.09590.53910.073*0.516 (4)
C50.81201 (19)0.0153 (11)0.5163 (2)0.0596 (12)0.516 (4)
H50.8246−0.07950.55590.072*0.516 (4)
C60.76244 (18)0.0498 (11)0.4682 (2)0.0551 (11)0.516 (4)
H60.7412−0.02140.47500.066*0.516 (4)
C1A0.74487 (19)0.1788 (12)0.4091 (2)0.0444 (5)0.484 (4)
C2A0.7774 (3)0.3742 (10)0.4168 (3)0.0565 (14)0.484 (4)
H2A0.76600.53500.38840.068*0.484 (4)
C3A0.8267 (3)0.3344 (11)0.4661 (4)0.0568 (13)0.484 (4)
H3A0.84900.46790.47140.068*0.484 (4)
C4A0.84344 (17)0.0991 (13)0.5077 (3)0.0611 (7)0.484 (4)
H4A0.87710.07190.54140.073*0.484 (4)
C5A0.8109 (2)−0.0963 (11)0.5000 (2)0.0596 (12)0.484 (4)
H5A0.8223−0.25710.52840.072*0.484 (4)
C6A0.76159 (19)−0.0564 (11)0.4507 (3)0.0551 (11)0.484 (4)
H6A0.7393−0.19000.44540.066*0.484 (4)
C70.66759 (7)0.4096 (4)0.31061 (9)0.0385 (5)
C80.61906 (7)0.3724 (4)0.28314 (10)0.0395 (5)
C90.61930 (8)0.1579 (4)0.32169 (11)0.0458 (5)
C100.57752 (8)0.0445 (5)0.31473 (12)0.0575 (6)
H10A0.5884−0.11180.34610.086*
H10B0.5530−0.02860.27030.086*
H10C0.56360.19910.32320.086*
C110.64643 (7)0.7328 (4)0.23600 (9)0.0360 (4)
C120.64814 (7)0.9456 (4)0.19683 (9)0.0368 (4)
C130.68659 (7)1.0487 (4)0.20208 (10)0.0424 (5)
H130.71850.98340.23590.051*
C140.67732 (8)1.2503 (5)0.15671 (10)0.0470 (5)
H140.70321.32280.15940.056*
C150.63093 (8)1.3466 (5)0.10772 (10)0.0480 (5)
H150.62551.48500.07740.058*
C160.59220 (7)1.2445 (4)0.10213 (10)0.0440 (5)
H160.56041.31250.06840.053*
C170.60064 (7)1.0419 (4)0.14650 (9)0.0387 (5)
C180.56731 (7)0.8908 (4)0.15189 (9)0.0389 (5)
C190.59741 (7)0.6983 (4)0.20825 (9)0.0379 (4)
C200.51870 (7)0.9165 (4)0.11397 (10)0.0421 (5)
C210.49030 (8)0.7526 (5)0.12444 (11)0.0499 (5)
C220.49111 (8)1.1104 (5)0.05965 (11)0.0491 (5)
U11U22U33U12U13U23
N10.0487 (10)0.0408 (9)0.0452 (10)0.0038 (8)0.0331 (9)0.0037 (8)
N20.0606 (12)0.0437 (10)0.0563 (11)0.0011 (9)0.0447 (11)0.0022 (9)
N30.0421 (9)0.0351 (9)0.0406 (9)0.0017 (7)0.0274 (8)−0.0007 (7)
N40.0452 (10)0.0383 (9)0.0471 (10)−0.0017 (8)0.0318 (9)−0.0063 (8)
N50.0494 (12)0.0848 (16)0.0745 (15)−0.0056 (11)0.0418 (12)−0.0071 (12)
N60.0538 (12)0.0703 (14)0.0579 (13)0.0127 (11)0.0287 (11)0.0066 (12)
C10.0527 (13)0.0398 (12)0.0459 (12)0.0081 (10)0.0339 (11)0.0016 (9)
C20.0545 (17)0.058 (3)0.060 (3)0.018 (2)0.037 (2)0.020 (3)
C30.0543 (17)0.058 (3)0.063 (4)0.015 (2)0.040 (2)0.006 (2)
C40.0583 (15)0.0649 (17)0.0510 (14)0.0200 (13)0.0306 (13)0.0071 (13)
C50.073 (2)0.056 (3)0.047 (3)0.017 (3)0.038 (2)0.008 (2)
C60.0618 (18)0.054 (3)0.050 (3)0.006 (2)0.036 (2)0.006 (2)
C1A0.0527 (13)0.0398 (12)0.0459 (12)0.0081 (10)0.0339 (11)0.0016 (9)
C2A0.0545 (17)0.058 (3)0.060 (3)0.018 (2)0.037 (2)0.020 (3)
C3A0.0543 (17)0.058 (3)0.063 (4)0.015 (2)0.040 (2)0.006 (2)
C4A0.0583 (15)0.0649 (17)0.0510 (14)0.0200 (13)0.0306 (13)0.0071 (13)
C5A0.073 (2)0.056 (3)0.047 (3)0.017 (3)0.038 (2)0.008 (2)
C6A0.0618 (18)0.054 (3)0.050 (3)0.006 (2)0.036 (2)0.006 (2)
C70.0458 (11)0.0339 (10)0.0412 (11)0.0034 (9)0.0302 (10)−0.0016 (9)
C80.0460 (12)0.0344 (10)0.0469 (12)0.0009 (9)0.0337 (10)−0.0038 (9)
C90.0551 (13)0.0421 (11)0.0521 (13)−0.0012 (10)0.0398 (12)−0.0045 (10)
C100.0674 (15)0.0569 (14)0.0712 (16)−0.0045 (12)0.0548 (14)−0.0006 (12)
C110.0381 (11)0.0328 (10)0.0377 (10)0.0001 (8)0.0245 (9)−0.0044 (8)
C120.0396 (11)0.0326 (10)0.0381 (10)−0.0005 (8)0.0247 (9)−0.0043 (8)
C130.0393 (11)0.0429 (11)0.0410 (11)−0.0017 (9)0.0238 (10)−0.0040 (9)
C140.0468 (12)0.0497 (12)0.0511 (13)−0.0024 (10)0.0342 (11)−0.0006 (10)
C150.0541 (13)0.0479 (12)0.0446 (12)0.0024 (10)0.0327 (11)0.0035 (10)
C160.0442 (12)0.0431 (11)0.0404 (11)0.0038 (10)0.0249 (10)−0.0008 (9)
C170.0392 (11)0.0352 (10)0.0407 (11)0.0004 (8)0.0250 (9)−0.0051 (9)
C180.0410 (11)0.0352 (10)0.0409 (11)−0.0011 (8)0.0262 (10)−0.0088 (9)
C190.0394 (11)0.0345 (10)0.0409 (11)0.0003 (8)0.0261 (10)−0.0042 (8)
C200.0391 (11)0.0420 (11)0.0411 (11)0.0023 (9)0.0238 (10)−0.0052 (9)
C210.0392 (12)0.0558 (13)0.0516 (13)−0.0009 (11)0.0274 (11)−0.0101 (11)
C220.0412 (12)0.0528 (13)0.0481 (13)0.0026 (11)0.0261 (11)−0.0072 (11)
N1—C71.361 (2)C4A—C5A1.3900
N1—N21.391 (2)C4A—H4A0.9500
N1—C11.403 (5)C5A—C6A1.3900
N1—C1A1.430 (5)C5A—H5A0.9500
N2—C91.311 (3)C6A—H6A0.9500
N3—C111.328 (2)C7—C81.409 (3)
N3—C71.353 (2)C8—C91.426 (3)
N4—C191.327 (2)C9—C101.489 (3)
N4—C81.342 (3)C10—H10A0.9800
N5—C211.147 (3)C10—H10B0.9800
N6—C221.148 (3)C10—H10C0.9800
C1—C21.3900C11—C191.421 (3)
C1—C61.3900C11—C121.466 (3)
C2—C31.3900C12—C131.384 (3)
C2—H20.9500C12—C171.413 (3)
C3—C41.3900C13—C141.390 (3)
C3—H30.9500C13—H130.9500
C4—C51.3900C14—C151.382 (3)
C4—H40.9500C14—H140.9500
C5—C61.3900C15—C161.387 (3)
C5—H50.9500C15—H150.9500
C6—H60.9500C16—C171.384 (3)
C1A—C2A1.3900C16—H160.9500
C1A—C6A1.3900C17—C181.474 (3)
C2A—C3A1.3900C18—C201.356 (3)
C2A—H2A0.9500C18—C191.466 (3)
C3A—C4A1.3900C20—C221.434 (3)
C3A—H3A0.9500C20—C211.437 (3)
C7—N1—N2110.14 (16)N1—C7—C8106.37 (17)
C7—N1—C1131.2 (3)N4—C8—C7123.33 (18)
N2—N1—C1118.4 (3)N4—C8—C9130.67 (19)
C7—N1—C1A131.0 (3)C7—C8—C9105.99 (18)
N2—N1—C1A118.8 (3)N2—C9—C8109.54 (18)
C9—N2—N1107.95 (16)N2—C9—C10122.5 (2)
C11—N3—C7110.46 (16)C8—C9—C10128.0 (2)
C19—N4—C8111.93 (16)C9—C10—H10A109.5
C2—C1—C6120.0C9—C10—H10B109.5
C2—C1—N1120.3 (4)H10A—C10—H10B109.5
C6—C1—N1119.7 (4)C9—C10—H10C109.5
C3—C2—C1120.0H10A—C10—H10C109.5
C3—C2—H2120.0H10B—C10—H10C109.5
C1—C2—H2120.0N3—C11—C19124.72 (17)
C2—C3—C4120.0N3—C11—C12127.38 (17)
C2—C3—H3120.0C19—C11—C12107.90 (16)
C4—C3—H3120.0C13—C12—C17120.84 (18)
C5—C4—C3120.0C13—C12—C11130.85 (18)
C5—C4—H4120.0C17—C12—C11108.30 (16)
C3—C4—H4120.0C12—C13—C14118.35 (19)
C6—C5—C4120.0C12—C13—H13120.8
C6—C5—H5120.0C14—C13—H13120.8
C4—C5—H5120.0C15—C14—C13120.9 (2)
C5—C6—C1120.0C15—C14—H14119.5
C5—C6—H6120.0C13—C14—H14119.5
C1—C6—H6120.0C14—C15—C16121.1 (2)
C2A—C1A—C6A120.0C14—C15—H15119.4
C2A—C1A—N1121.3 (4)C16—C15—H15119.4
C6A—C1A—N1118.5 (4)C17—C16—C15118.82 (19)
C1A—C2A—C3A120.0C17—C16—H16120.6
C1A—C2A—H2A120.0C15—C16—H16120.6
C3A—C2A—H2A120.0C16—C17—C12119.95 (18)
C4A—C3A—C2A120.0C16—C17—C18131.13 (18)
C4A—C3A—H3A120.0C12—C17—C18108.91 (17)
C2A—C3A—H3A120.0C20—C18—C19125.14 (18)
C5A—C4A—C3A120.0C20—C18—C17128.95 (19)
C5A—C4A—H4A120.0C19—C18—C17105.91 (16)
C3A—C4A—H4A120.0N4—C19—C11124.33 (18)
C4A—C5A—C6A120.0N4—C19—C18126.69 (17)
C4A—C5A—H5A120.0C11—C19—C18108.98 (17)
C6A—C5A—H5A120.0C18—C20—C22122.7 (2)
C5A—C6A—C1A120.0C18—C20—C21123.22 (19)
C5A—C6A—H6A120.0C22—C20—C21114.06 (18)
C1A—C6A—H6A120.0N5—C21—C20176.0 (2)
N3—C7—N1128.40 (18)N6—C22—C20178.4 (2)
N3—C7—C8125.22 (18)
C7—N1—N2—C9−0.6 (2)N3—C7—C8—C9178.93 (17)
C1—N1—N2—C9174.4 (2)N1—C7—C8—C90.0 (2)
C1A—N1—N2—C9177.4 (3)N1—N2—C9—C80.6 (2)
C7—N1—C1—C2−18.7 (4)N1—N2—C9—C10−177.98 (18)
N2—N1—C1—C2167.6 (2)N4—C8—C9—N2178.80 (19)
C1A—N1—C1—C269 (11)C7—C8—C9—N2−0.3 (2)
C7—N1—C1—C6160.6 (3)N4—C8—C9—C10−2.8 (4)
N2—N1—C1—C6−13.1 (4)C7—C8—C9—C10178.1 (2)
C1A—N1—C1—C6−112 (11)C7—N3—C11—C190.2 (3)
C6—C1—C2—C30.0C7—N3—C11—C12−179.09 (17)
N1—C1—C2—C3179.3 (4)N3—C11—C12—C131.4 (3)
C1—C2—C3—C40.0C19—C11—C12—C13−177.97 (19)
C2—C3—C4—C50.0N3—C11—C12—C17−179.69 (18)
C3—C4—C5—C60.0C19—C11—C12—C170.9 (2)
C4—C5—C6—C10.0C17—C12—C13—C140.2 (3)
C2—C1—C6—C50.0C11—C12—C13—C14178.95 (19)
N1—C1—C6—C5−179.3 (4)C12—C13—C14—C150.3 (3)
C7—N1—C1A—C2A14.8 (4)C13—C14—C15—C16−0.3 (3)
N2—N1—C1A—C2A−162.6 (3)C14—C15—C16—C17−0.3 (3)
C1—N1—C1A—C2A−80 (11)C15—C16—C17—C120.8 (3)
C7—N1—C1A—C6A−169.9 (3)C15—C16—C17—C18−178.22 (19)
N2—N1—C1A—C6A12.7 (4)C13—C12—C17—C16−0.8 (3)
C1—N1—C1A—C6A95 (11)C11—C12—C17—C16−179.76 (17)
C6A—C1A—C2A—C3A0.0C13—C12—C17—C18178.45 (17)
N1—C1A—C2A—C3A175.2 (4)C11—C12—C17—C18−0.6 (2)
C1A—C2A—C3A—C4A0.0C16—C17—C18—C20−0.9 (3)
C2A—C3A—C4A—C5A0.0C12—C17—C18—C20179.99 (19)
C3A—C4A—C5A—C6A0.0C16—C17—C18—C19179.1 (2)
C4A—C5A—C6A—C1A0.0C12—C17—C18—C190.0 (2)
C2A—C1A—C6A—C5A0.0C8—N4—C19—C110.8 (3)
N1—C1A—C6A—C5A−175.3 (4)C8—N4—C19—C18−179.82 (17)
C11—N3—C7—N1179.02 (18)N3—C11—C19—N4−0.8 (3)
C11—N3—C7—C80.3 (3)C12—C11—C19—N4178.58 (17)
N2—N1—C7—N3−178.56 (18)N3—C11—C19—C18179.68 (17)
C1—N1—C7—N37.3 (4)C12—C11—C19—C18−0.9 (2)
C1A—N1—C7—N33.8 (4)C20—C18—C19—N41.1 (3)
N2—N1—C7—C80.4 (2)C17—C18—C19—N4−178.91 (18)
C1—N1—C7—C8−173.8 (3)C20—C18—C19—C11−179.43 (18)
C1A—N1—C7—C8−177.2 (3)C17—C18—C19—C110.6 (2)
C19—N4—C8—C7−0.3 (3)C19—C18—C20—C22179.49 (18)
C19—N4—C8—C9−179.28 (19)C17—C18—C20—C22−0.5 (3)
N3—C7—C8—N4−0.3 (3)C19—C18—C20—C21−0.6 (3)
N1—C7—C8—N4−179.24 (17)C17—C18—C20—C21179.43 (18)
D—H···AD—HH···AD···AD—H···A
C10—H10A···N5i0.982.693.362 (3)126
Table 1

Hydrogen-bond geometry (, )

DHA DHHA D A DHA
C10H10AN5i 0.982.693.362(3)126

Symmetry code: (i) .

  7 in total

1.  Design, synthesis, and biological evaluation of novel tricyclic HIV-1 integrase inhibitors by modification of its pyridine ring.

Authors:  Sammy E Metobo; Haolun Jin; Manuel Tsiang; Choung U Kim
Journal:  Bioorg Med Chem Lett       Date:  2006-05-24       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.  Analgesic activity of new pyrazine CH and NH acids and their hydrophobic and electron donating properties.

Authors:  R Kaliszan; B Pilarski; K Ośmiałowski; H Strzałkowska-Grad; E Hać
Journal:  Pharm Weekbl Sci       Date:  1985-08-23

4.  First synthesis and biological evaluation of indeno[2,1-e]pyrazolo[3,4-b]pyrazin-5-one and related derivatives.

Authors:  Talaat El-Emary; Hussein El-Kashef
Journal:  Eur J Med Chem       Date:  2013-01-26       Impact factor: 6.514

5.  Structure activity relationship studies of imidazo[1,2-a]pyrazine derivatives against cancer cell lines.

Authors:  Shailaja Myadaraboina; Manjula Alla; Venkateshwarlu Saddanapu; Vittal Rao Bommena; Anthony Addlagatta
Journal:  Eur J Med Chem       Date:  2010-08-18       Impact factor: 6.514

6.  Studies on antiallergic agents. I. Synthesis and antiallergic activity of novel pyrazine derivatives.

Authors:  E Makino; N Iwasaki; N Yagi; T Ohashi; H Kato; Y Ito; H Azuma
Journal:  Chem Pharm Bull (Tokyo)       Date:  1990-01       Impact factor: 1.645

7.  A micropuncture study on the renal site of action of ICI 206,970, a unique eukalemic diuretic.

Authors:  P A Johnston; S T Kau
Journal:  J Pharmacol Exp Ther       Date:  1993-02       Impact factor: 4.030
  7 in total
  1 in total

1.  Crystal structure of N-[(8E)-12-methyl-14-phenyl-10,13,14,16-tetra-aza-tetra-cyclo-[7.7.0.0(2,7).0(11,15)]hexa-deca-1(16),2,4,6,9,11(15),12-heptaen-8-yl-idene]hydroxyl-amine 1,4-dioxane hemisolvate.

Authors:  Shaaban K Mohamed; Joel T Mague; Mehmet Akkurt; Talaat I El-Emary; Mustafa R Albayati
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-01-03
  1 in total

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