3-Acetyl-5-phenyl-1-p-tolyl-1H-pyrazole-4-carbonitrile

Abdel-Aziz, H.A.; Ghabbour, H.A.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536812011762

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1167

doi:10.1107/S1600536812011762

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3-Acetyl-5-phenyl-1-p-tolyl-1H-pyrazole-4-carbonitrile

Hatem A. Abdel-Aziz,^a Hazem A. Ghabbour,^a Suchada Chantrapromma ^b ‡ and Hoong-Kun Fun ^c ^*§

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 16 March 2012; accepted 19 March 2012; online 24 March 2012)

In the title pyrazole derivative, C₁₉H₁₅N₃O, the central pyrazole ring makes dihedral angles of 42.71 (9) and 61.34 (9)°, respectively, with the phenyl and p-tolyl rings. The dihedral angle between the phenyl and p-tolyl rings is 58.22 (9)°. The 3-acetyl-1H-pyrazole-4-carbonitrile unit is essentially planar, with an r.m.s. deviation of 0.0295 (1) Å for the ten non-H atoms.

Related literature

For bond-length data, see: Allen et al. (1987 ). For background to and the bioactivity of pyrazole derivatives, see: Abdel-Aziz et al. (2009 , 2010 ); Abdel-Wahab et al. (2009 ); Dawood et al. (2003 ). For a related structure, see: Abdel-Aziz et al. (2012 ).

Experimental

Crystal data

C₁₉H₁₅N₃O
M_r = 301.34
Monoclinic, P 2₁ /c
a = 10.2433 (2) Å
b = 10.6467 (2) Å
c = 15.7547 (3) Å
β = 109.684 (1)°
V = 1617.76 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.63 mm⁻¹
T = 296 K
0.57 × 0.28 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.718, T_max = 0.876
10344 measured reflections
2720 independent reflections
2427 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.118
S = 1.05
2720 reflections
213 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812011762/is5093sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812011762/is5093Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812011762/is5093Isup3.cml

checkCIF report

Comment top

During the course of our medicinal chemistry research on pyrazole derivatives (Abdel-Aziz et al., 2009, 2010; Abdel-Wahab et al., 2009), we previously reported the crystal structure of 3-acetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile (I) (Abdel-Aziz et al., 2012). The title compound (II), was synthesized by retaining the core part but changing the phenyl group which was attached to N atom at position 1 of the pyrazole ring in compound (I) to the p-tolyl in order to investigate the influence of the substituents to their biological properties. Herein, the crystal structure of (II) was reported.

The molecule of (II), C₁₉H₁₅N₃O, has the same butterfly-like structure as in (I) (Abdel-Aziz et al., 2012). However there are differences in the dihedral angles between the equivalent moieties and the crystal packing of (I) and (II). In (II), the pyrazole ring forms dihedral angles of 42.71 (9) and 61.34 (9)°, respectively, with the C5–C10 and C11-C16 benzene rings [the corresponding values in (I) are 59.31 (8) and 57.24 (8)° ] and the dihedral angle between these two benzene rings is 58.22 (9)° [the corresponding value in (I) is 64.03 (8)°]. The cabonitrile and acetyl substituents in (II) lie essentially on the same plane with the pyrazole ring with the r.m.s. 0.0295 (1) Å for the ten non H atoms (C1–C4/C17/C18/N1–N3/O1) and the dihedral angle between the C-C=O planes of the acetyl unit and pyrazole ring is 4.8 (2)° [whereas in (I) the acetyl moiety is slightly deviated from the pyrazole ring with the dihedral angle between the C-C=O planes of the acetyl and pyrazole moieties being 7.95 (18)°]. The bond distances in (II) are within normal ranges (Allen et al., 1987) and are comparable to the closely related structure (Abdel-Aziz et al., 2012). The crystal packing of (II) is stabilized by van der Waals interactions. Even there is no hydrogen bonds, the crystal packing of (II) was shown in Fig. 2 for comparison with that of (I).

Related literature top

For bond-length data, see: Allen et al. (1987). For background to and the bioactivity of pyrazole derivatives, see: Abdel-Aziz et al. (2009, 2010); Abdel-Wahab et al. (2009); Dawood et al. (2003). For a related structure, see: Abdel-Aziz et al. (2012).

Experimental top

The title compound was prepared according to the reported method (Dawood et al., 2003). Single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by the slow evaporation of the solvent at room temperature after several days.

Structure description top

For bond-length data, see: Allen et al. (1987). For background to and the bioactivity of pyrazole derivatives, see: Abdel-Aziz et al. (2009, 2010); Abdel-Wahab et al. (2009); Dawood et al. (2003). For a related structure, see: Abdel-Aziz et al. (2012).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of the title compound, showing 40% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A packing diagram of the title compound viewed along the a axis.

3-Acetyl-5-phenyl-1-p-tolyl-1H-pyrazole-4-carbonitrile top

Crystal data top

C₁₉H₁₅N₃O	F(000) = 632
M_r = 301.34	D_x = 1.237 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 272 reflections
a = 10.2433 (2) Å	θ = 4.6–65.0°
b = 10.6467 (2) Å	µ = 0.63 mm⁻¹
c = 15.7547 (3) Å	T = 296 K
β = 109.684 (1)°	Block, colorless
V = 1617.76 (5) Å³	0.57 × 0.28 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2720 independent reflections
Radiation source: sealed tube	2427 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 65.0°, θ_min = 4.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→11
T_min = 0.718, T_max = 0.876	k = −12→12
10344 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.118	w = 1/[σ²(F_o²) + (0.050P)² + 0.2871P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2720 reflections	Δρ_max = 0.20 e Å⁻³
213 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0113 (9)

Crystal data top

C₁₉H₁₅N₃O	V = 1617.76 (5) Å³
M_r = 301.34	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 10.2433 (2) Å	µ = 0.63 mm⁻¹
b = 10.6467 (2) Å	T = 296 K
c = 15.7547 (3) Å	0.57 × 0.28 × 0.22 mm
β = 109.684 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2720 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2427 reflections with I > 2σ(I)
T_min = 0.718, T_max = 0.876	R_int = 0.032
10344 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
2720 reflections	Δρ_min = −0.14 e Å⁻³
213 parameters

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	U_iso*/U_eq
O1	−0.28761 (14)	0.55281 (14)	0.42141 (9)	0.0837 (4)
N1	0.05513 (13)	0.54275 (12)	0.68539 (8)	0.0536 (3)
N2	−0.05757 (13)	0.47588 (13)	0.63730 (8)	0.0585 (3)
N3	−0.07458 (17)	0.81153 (17)	0.43476 (10)	0.0795 (5)
C1	−0.11442 (15)	0.54122 (15)	0.56191 (10)	0.0544 (4)
C2	−0.03698 (14)	0.65058 (14)	0.56181 (9)	0.0513 (4)
C3	0.07256 (14)	0.64969 (14)	0.64318 (9)	0.0499 (4)
C4	−0.05890 (15)	0.74023 (16)	0.49130 (10)	0.0578 (4)
C5	0.18570 (15)	0.74010 (15)	0.67940 (9)	0.0521 (4)
C6	0.15724 (18)	0.86766 (16)	0.67039 (11)	0.0637 (4)
H6A	0.0669	0.8947	0.6412	0.076*
C7	0.2610 (2)	0.9544 (2)	0.70412 (14)	0.0833 (6)
H7A	0.2405	1.0398	0.6983	0.100*
C8	0.3956 (2)	0.9150 (2)	0.74673 (14)	0.0876 (6)
H8A	0.4659	0.9736	0.7699	0.105*
C9	0.42553 (18)	0.7887 (2)	0.75483 (13)	0.0781 (6)
H9A	0.5165	0.7624	0.7828	0.094*
C10	0.32237 (16)	0.70133 (18)	0.72207 (11)	0.0644 (4)
H10A	0.3435	0.6161	0.7283	0.077*
C11	0.13953 (15)	0.49602 (15)	0.77206 (9)	0.0530 (4)
C12	0.15432 (17)	0.56511 (16)	0.84811 (10)	0.0587 (4)
H12A	0.1096	0.6420	0.8442	0.070*
C13	0.23678 (17)	0.51883 (17)	0.93088 (10)	0.0625 (4)
H13A	0.2470	0.5654	0.9827	0.075*
C14	0.30436 (16)	0.40481 (17)	0.93820 (10)	0.0605 (4)
C15	0.2845 (2)	0.33649 (18)	0.86054 (12)	0.0723 (5)
H15A	0.3274	0.2587	0.8644	0.087*
C16	0.2024 (2)	0.38067 (17)	0.77706 (11)	0.0690 (5)
H16A	0.1900	0.3334	0.7253	0.083*
C17	−0.24206 (18)	0.49704 (17)	0.49213 (11)	0.0641 (4)
C18	−0.3103 (2)	0.3819 (2)	0.51218 (15)	0.0947 (7)
H18A	−0.3925	0.3639	0.4621	0.142*
H18B	−0.3346	0.3959	0.5652	0.142*
H18C	−0.2475	0.3122	0.5222	0.142*
C19	0.39693 (19)	0.3572 (2)	1.02859 (12)	0.0778 (5)
H19C	0.3602	0.2800	1.0425	0.117*
H19A	0.4011	0.4185	1.0741	0.117*
H19B	0.4884	0.3429	1.0266	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0771 (8)	0.0812 (9)	0.0701 (8)	0.0013 (7)	−0.0049 (6)	0.0061 (7)
N1	0.0510 (7)	0.0597 (7)	0.0486 (6)	0.0035 (5)	0.0147 (5)	0.0065 (5)
N2	0.0554 (7)	0.0637 (8)	0.0545 (7)	0.0002 (6)	0.0162 (6)	0.0032 (6)
N3	0.0781 (10)	0.0908 (11)	0.0680 (9)	0.0115 (8)	0.0223 (7)	0.0254 (9)
C1	0.0505 (8)	0.0616 (9)	0.0511 (8)	0.0074 (7)	0.0171 (6)	0.0015 (7)
C2	0.0465 (7)	0.0596 (8)	0.0488 (7)	0.0116 (6)	0.0171 (6)	0.0055 (6)
C3	0.0453 (7)	0.0566 (8)	0.0503 (7)	0.0093 (6)	0.0194 (6)	0.0063 (6)
C4	0.0488 (8)	0.0695 (10)	0.0540 (8)	0.0105 (7)	0.0161 (6)	0.0076 (8)
C5	0.0471 (7)	0.0632 (9)	0.0467 (7)	0.0054 (6)	0.0169 (6)	0.0085 (6)
C6	0.0585 (9)	0.0638 (10)	0.0639 (9)	0.0070 (7)	0.0144 (7)	0.0091 (7)
C7	0.0894 (14)	0.0662 (11)	0.0825 (12)	−0.0095 (10)	0.0134 (10)	0.0130 (9)
C8	0.0761 (12)	0.0946 (15)	0.0774 (12)	−0.0279 (11)	0.0067 (9)	0.0208 (11)
C9	0.0497 (9)	0.1040 (15)	0.0710 (10)	−0.0060 (9)	0.0075 (7)	0.0297 (10)
C10	0.0502 (8)	0.0743 (10)	0.0661 (9)	0.0068 (7)	0.0163 (7)	0.0184 (8)
C11	0.0500 (8)	0.0608 (9)	0.0486 (7)	0.0026 (6)	0.0172 (6)	0.0099 (6)
C12	0.0587 (9)	0.0603 (9)	0.0573 (8)	0.0057 (7)	0.0198 (7)	0.0049 (7)
C13	0.0638 (9)	0.0709 (10)	0.0504 (8)	−0.0040 (8)	0.0162 (7)	0.0027 (7)
C14	0.0503 (8)	0.0732 (10)	0.0569 (8)	−0.0028 (7)	0.0168 (7)	0.0164 (8)
C15	0.0816 (12)	0.0679 (10)	0.0680 (10)	0.0210 (9)	0.0259 (9)	0.0178 (8)
C16	0.0836 (12)	0.0681 (10)	0.0553 (9)	0.0156 (9)	0.0234 (8)	0.0060 (8)
C17	0.0581 (9)	0.0690 (10)	0.0606 (9)	0.0049 (8)	0.0139 (7)	−0.0033 (8)
C18	0.0866 (14)	0.1014 (16)	0.0848 (13)	−0.0296 (12)	0.0139 (11)	0.0028 (12)
C19	0.0634 (10)	0.0968 (14)	0.0650 (10)	0.0000 (9)	0.0110 (8)	0.0238 (10)

Geometric parameters (Å, º) top

O1—C17	1.209 (2)	C9—H9A	0.9300
N1—N2	1.3507 (18)	C10—H10A	0.9300
N1—C3	1.3603 (19)	C11—C12	1.370 (2)
N1—C11	1.4367 (18)	C11—C16	1.377 (2)
N2—C1	1.330 (2)	C12—C13	1.384 (2)
N3—C4	1.140 (2)	C12—H12A	0.9300
C1—C2	1.409 (2)	C13—C14	1.383 (3)
C1—C17	1.473 (2)	C13—H13A	0.9300
C2—C3	1.390 (2)	C14—C15	1.378 (3)
C2—C4	1.424 (2)	C14—C19	1.508 (2)
C3—C5	1.466 (2)	C15—C16	1.383 (2)
C5—C6	1.386 (2)	C15—H15A	0.9300
C5—C10	1.396 (2)	C16—H16A	0.9300
C6—C7	1.373 (3)	C17—C18	1.496 (3)
C6—H6A	0.9300	C18—H18A	0.9600
C7—C8	1.380 (3)	C18—H18B	0.9600
C7—H7A	0.9300	C18—H18C	0.9600
C8—C9	1.375 (3)	C19—H19C	0.9600
C8—H8A	0.9300	C19—H19A	0.9600
C9—C10	1.372 (3)	C19—H19B	0.9600

N2—N1—C3	113.27 (12)	C12—C11—N1	119.94 (14)
N2—N1—C11	118.53 (12)	C16—C11—N1	118.91 (14)
C3—N1—C11	128.20 (13)	C11—C12—C13	119.05 (15)
C1—N2—N1	105.05 (13)	C11—C12—H12A	120.5
N2—C1—C2	110.85 (13)	C13—C12—H12A	120.5
N2—C1—C17	120.73 (15)	C14—C13—C12	121.38 (16)
C2—C1—C17	128.41 (14)	C14—C13—H13A	119.3
C3—C2—C1	105.85 (13)	C12—C13—H13A	119.3
C3—C2—C4	126.16 (14)	C15—C14—C13	117.98 (14)
C1—C2—C4	127.87 (13)	C15—C14—C19	121.26 (17)
N1—C3—C2	104.97 (13)	C13—C14—C19	120.77 (17)
N1—C3—C5	125.17 (13)	C14—C15—C16	121.69 (16)
C2—C3—C5	129.86 (13)	C14—C15—H15A	119.2
N3—C4—C2	178.98 (17)	C16—C15—H15A	119.2
C6—C5—C10	118.77 (16)	C11—C16—C15	118.74 (16)
C6—C5—C3	119.47 (13)	C11—C16—H16A	120.6
C10—C5—C3	121.76 (15)	C15—C16—H16A	120.6
C7—C6—C5	120.73 (16)	O1—C17—C1	120.06 (17)
C7—C6—H6A	119.6	O1—C17—C18	122.28 (17)
C5—C6—H6A	119.6	C1—C17—C18	117.66 (16)
C6—C7—C8	119.97 (19)	C17—C18—H18A	109.5
C6—C7—H7A	120.0	C17—C18—H18B	109.5
C8—C7—H7A	120.0	H18A—C18—H18B	109.5
C9—C8—C7	119.85 (19)	C17—C18—H18C	109.5
C9—C8—H8A	120.1	H18A—C18—H18C	109.5
C7—C8—H8A	120.1	H18B—C18—H18C	109.5
C10—C9—C8	120.58 (17)	C14—C19—H19C	109.5
C10—C9—H9A	119.7	C14—C19—H19A	109.5
C8—C9—H9A	119.7	H19C—C19—H19A	109.5
C9—C10—C5	120.08 (17)	C14—C19—H19B	109.5
C9—C10—H10A	120.0	H19C—C19—H19B	109.5
C5—C10—H10A	120.0	H19A—C19—H19B	109.5
C12—C11—C16	121.13 (14)

C3—N1—N2—C1	0.11 (16)	C6—C7—C8—C9	0.4 (3)
C11—N1—N2—C1	179.67 (13)	C7—C8—C9—C10	−1.0 (3)
N1—N2—C1—C2	0.18 (16)	C8—C9—C10—C5	0.5 (3)
N1—N2—C1—C17	−179.55 (13)	C6—C5—C10—C9	0.5 (2)
N2—C1—C2—C3	−0.39 (16)	C3—C5—C10—C9	179.78 (15)
C17—C1—C2—C3	179.31 (15)	N2—N1—C11—C12	−117.95 (16)
N2—C1—C2—C4	175.73 (14)	C3—N1—C11—C12	61.5 (2)
C17—C1—C2—C4	−4.6 (2)	N2—N1—C11—C16	60.91 (19)
N2—N1—C3—C2	−0.35 (16)	C3—N1—C11—C16	−119.60 (18)
C11—N1—C3—C2	−179.86 (13)	C16—C11—C12—C13	1.6 (2)
N2—N1—C3—C5	−179.96 (13)	N1—C11—C12—C13	−179.59 (14)
C11—N1—C3—C5	0.5 (2)	C11—C12—C13—C14	0.1 (3)
C1—C2—C3—N1	0.43 (15)	C12—C13—C14—C15	−1.6 (2)
C4—C2—C3—N1	−175.78 (13)	C12—C13—C14—C19	178.34 (16)
C1—C2—C3—C5	−179.98 (14)	C13—C14—C15—C16	1.5 (3)
C4—C2—C3—C5	3.8 (2)	C19—C14—C15—C16	−178.44 (18)
N1—C3—C5—C6	−138.02 (15)	C12—C11—C16—C15	−1.7 (3)
C2—C3—C5—C6	42.5 (2)	N1—C11—C16—C15	179.48 (16)
N1—C3—C5—C10	42.7 (2)	C14—C15—C16—C11	0.1 (3)
C2—C3—C5—C10	−136.79 (16)	N2—C1—C17—O1	−175.12 (16)
C10—C5—C6—C7	−1.1 (3)	C2—C1—C17—O1	5.2 (3)
C3—C5—C6—C7	179.61 (16)	N2—C1—C17—C18	4.4 (2)
C5—C6—C7—C8	0.7 (3)	C2—C1—C17—C18	−175.32 (18)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅N₃O
M_r	301.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.2433 (2), 10.6467 (2), 15.7547 (3)
β (°)	109.684 (1)
V (Å³)	1617.76 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.57 × 0.28 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.718, 0.876
No. of measured, independent and observed [I > 2σ(I)] reflections	10344, 2720, 2427
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.588

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.118, 1.05
No. of reflections	2720
No. of parameters	213
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.14

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§College of Pharmacy (Visiting Professor), King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University, and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. HKF also thanks the King Saud University, Riyadh, Saudi Arabia, for the award of a visiting Professorship (December 23rd 2011 to January 14th 2012).

References

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