2,2-Dimethyl-5-[(3-nitro­anilino)methyl­ene]-1,3-dioxane-4,6-dione

Zhou, M.; Li, R.; Ding, Z.-Y.

doi:10.1107/S1600536809031535

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2171

doi:10.1107/S1600536809031535

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2,2-Dimethyl-5-[(3-nitroanilino)methylene]-1,3-dioxane-4,6-dione

Meng Zhou,^a Rui Li ^a ^* and Zhen-Yu Ding ^a

^aState Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, People's Republic of China
^*Correspondence e-mail: lirui@scu.edu.cn

(Received 29 July 2009; accepted 10 August 2009; online 15 August 2009)

The benzene ring of the title compound, C₁₃H₁₂N₂O₆, is twisted away from the planes of the aminomethylene unit and the dioxane ring by 30.13 (4) and 35.89 (4)°, respectively. The dioxane ring exhibits a half-boat conformation, in which the C atom between the dioxane O atoms is 0.553 (8) Å out-of-plane. An intramolecular N—H⋯O hydrogen bond stabilizes the conformation of the dioxane ring with the aminomethylene group [the dihedral angle between the mean planes of the dioxane ring and the aminomethylene group is 11.61 (4)°]. In the crystal, a three-dimensional framework is built via weak intermolecular N—H⋯O and C—H⋯O interactions.

Related literature

For the synthesis of related compounds, see: Cassis et al. (1985 ). For the synthesis of related antitumor precursors, see Ruchelman et al. (2003 ). For the crystal structures of related 5-arylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives, see Li et al. (2009a ,b ); Li, Shi et al. (2009 ).

Experimental

Crystal data

C₁₃H₁₂N₂O₆
M_r = 292.25
Monoclinic, P 2₁ /c
a = 11.7900 (13) Å
b = 8.7699 (9) Å
c = 14.0614 (15) Å
β = 113.8640 (10)°
V = 1329.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 153 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
8116 measured reflections
3052 independent reflections
2572 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.101
S = 1.05
3052 reflections
197 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.882 (16)	2.150 (15)	2.7705 (14)	126.8 (13)
N1—H1⋯O3ⁱ	0.882 (16)	2.308 (16)	3.1101 (14)	151.2 (13)
C7—H7⋯O4ⁱⁱ	0.93	2.58	3.4527 (18)	156
C11—H11⋯O4ⁱⁱⁱ	0.93	2.39	3.242 (2)	152
C13—H13⋯O4ⁱⁱ	0.93	2.36	3.205 (2)	151
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x, -y, -z+2; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2000 ); data reduction: SAINT; 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: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031535/zq2002sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031535/zq2002Isup2.hkl

checkCIF report

Comment top

The 4(1H)quinolone structure have long attracted pharmacological interest as anticancer agents, anti-malarial agents and reversible (H+/K+) ATPase inhibitors (Ruchelman et al., 2003). 5-Arylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-diones are the key intermediates which can be used to synthesize the 4(1H)quinolone derivatives by thermolysis (Cassis et al., 1985).

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the mean planes formed by the benzyl and aminomethylene units is 30.13 (4)°, while the angle between the mean planes of the dioxane ring and the aminomethylene group is only 11.61 (4)° due to the intramolecular N1—H1···O3 hydrogen bond (Table 1). Apart from that, the dioxane ring exhibits a half-boat conformation, in which the C atom between the dioxane oxygen atoms is 0.553 (8) Å out-of-plane.

The three-dimensional framework is built by the weak intermolecular N1—H1···O3ⁱ, C7—H7···O4ⁱⁱ, C13—H13···O4ⁱⁱ and C11—H11···O4ⁱⁱⁱ interactions (Fig. 2).

Related literature top

For the synthesis of related compounds, see: Cassis et al. (1985). For the synthesis of related antitumor precursors, see Ruchelman et al. (2003). For the crystal structures of related 5-arylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives, see Li et al. (2009a,b); Li, Shi et al. (2009).

Experimental top

An ethanol solution (50 ml) of 2,2-dimethyl-1,3-dioxane-4,6-dione (1.44 g, 0.01 mol) and methylorthoformate (1.27 g, 0.012 mol) was heated to reflux for 1 h, then the 3-nitrobenzenamine (1.38 g, 0.01 mol) was added into the solution. The mixture was heated under reflux for another 8 h and then filtered. Single crystals were obtained from the filtrate after 3 days.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. Crystal packing of the title compound, showing the intermolecular hydrogen bonds as dashed lines. [Symmetry codes: (i) -x + 1, -y, -z + 2; (ii) -x, -y, -z + 2].

2,2-Dimethyl-5-[(3-nitroanilino)methylene]-1,3-dioxane-4,6-dione top

Crystal data top

C₁₃H₁₂N₂O₆	F(000) = 608
M_r = 292.25	D_x = 1.460 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.7900 (13) Å	Cell parameters from 4305 reflections
b = 8.7699 (9) Å	θ = 2.3–27.6°
c = 14.0614 (15) Å	µ = 0.12 mm⁻¹
β = 113.864 (1)°	T = 153 K
V = 1329.6 (2) Å³	Block, colourless
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2572 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.014
Graphite monochromator	θ_max = 27.6°, θ_min = 2.8°
ϕ and ω scans	h = −15→14
8116 measured reflections	k = −11→10
3052 independent reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.045P)² + 0.3157P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3052 reflections	Δρ_max = 0.22 e Å⁻³
197 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0195 (18)

Crystal data top

C₁₃H₁₂N₂O₆	V = 1329.6 (2) Å³
M_r = 292.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7900 (13) Å	µ = 0.12 mm⁻¹
b = 8.7699 (9) Å	T = 153 K
c = 14.0614 (15) Å	0.20 × 0.10 × 0.10 mm
β = 113.864 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2572 reflections with I > 2σ(I)
8116 measured reflections	R_int = 0.014
3052 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.22 e Å⁻³
3052 reflections	Δρ_min = −0.18 e Å⁻³
197 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.45433 (8)	−0.09916 (10)	1.23372 (6)	0.0370 (2)
O3	0.47419 (8)	−0.05487 (12)	1.08661 (7)	0.0440 (2)
O2	0.25826 (8)	−0.13984 (11)	1.23681 (6)	0.0401 (2)
C4	0.40464 (11)	−0.06725 (13)	1.13054 (9)	0.0322 (2)
N1	0.26298 (10)	0.01843 (13)	0.91248 (8)	0.0359 (2)
C8	0.19585 (11)	0.06369 (14)	0.80763 (9)	0.0342 (3)
C9	0.24224 (11)	0.02544 (14)	0.73506 (9)	0.0347 (3)
H9	0.3148	−0.0312	0.7538	0.042*
C3	0.37852 (11)	−0.07324 (14)	1.29110 (9)	0.0337 (3)
O4	0.08565 (9)	−0.12773 (15)	1.09442 (8)	0.0584 (3)
C7	0.21114 (11)	−0.01291 (14)	0.97781 (9)	0.0350 (3)
H7	0.1252	−0.0055	0.9519	0.042*
O5	0.30012 (13)	−0.07262 (15)	0.57581 (10)	0.0684 (3)
C6	0.19637 (11)	−0.10611 (15)	1.13438 (9)	0.0381 (3)
C5	0.27159 (11)	−0.05534 (14)	1.08029 (9)	0.0333 (3)
C10	0.17796 (12)	0.07365 (16)	0.63388 (9)	0.0403 (3)
C13	0.08587 (14)	0.14495 (19)	0.77793 (11)	0.0510 (4)
H13	0.0545	0.1705	0.8268	0.061*
C2	0.43836 (14)	−0.16096 (17)	1.39116 (10)	0.0459 (3)
H2A	0.3876	−0.1539	1.4299	0.069*
H2B	0.5188	−0.1189	1.4315	0.069*
H2C	0.4468	−0.2660	1.3759	0.069*
N2	0.22862 (12)	0.03454 (17)	0.55739 (9)	0.0535 (3)
C1	0.36712 (15)	0.09463 (15)	1.30692 (11)	0.0481 (3)
H1A	0.3285	0.1440	1.2406	0.072*
H1B	0.4481	0.1372	1.3444	0.072*
H1C	0.3174	0.1099	1.3459	0.072*
C11	0.06978 (15)	0.1552 (2)	0.60191 (11)	0.0586 (4)
H11	0.0293	0.1874	0.5334	0.070*
O6	0.19778 (16)	0.1124 (2)	0.47934 (10)	0.0992 (6)
C12	0.02320 (15)	0.1877 (2)	0.67512 (13)	0.0672 (5)
H12	−0.0518	0.2393	0.6550	0.081*
H1	0.3441 (15)	0.0100 (18)	0.9339 (12)	0.051 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0341 (4)	0.0496 (5)	0.0266 (4)	0.0047 (4)	0.0115 (3)	0.0028 (3)
O3	0.0338 (5)	0.0665 (6)	0.0354 (5)	0.0021 (4)	0.0177 (4)	0.0058 (4)
O2	0.0413 (5)	0.0500 (5)	0.0306 (4)	−0.0094 (4)	0.0164 (4)	0.0009 (4)
C4	0.0350 (6)	0.0351 (6)	0.0270 (5)	0.0005 (4)	0.0130 (5)	0.0007 (4)
N1	0.0313 (5)	0.0478 (6)	0.0274 (5)	0.0026 (4)	0.0106 (4)	0.0029 (4)
C8	0.0332 (6)	0.0396 (6)	0.0279 (5)	−0.0008 (5)	0.0105 (5)	0.0033 (5)
C9	0.0328 (6)	0.0388 (6)	0.0302 (6)	0.0001 (5)	0.0106 (5)	0.0030 (5)
C3	0.0375 (6)	0.0384 (6)	0.0263 (5)	−0.0019 (5)	0.0140 (5)	−0.0011 (4)
O4	0.0353 (5)	0.0966 (9)	0.0440 (6)	−0.0133 (5)	0.0167 (4)	0.0000 (5)
C7	0.0312 (6)	0.0427 (6)	0.0295 (6)	−0.0006 (5)	0.0108 (5)	−0.0006 (5)
O5	0.0855 (9)	0.0756 (8)	0.0587 (7)	0.0112 (7)	0.0443 (6)	−0.0031 (6)
C6	0.0352 (6)	0.0482 (7)	0.0324 (6)	−0.0042 (5)	0.0152 (5)	−0.0021 (5)
C5	0.0315 (6)	0.0409 (6)	0.0283 (5)	−0.0007 (5)	0.0128 (5)	−0.0004 (5)
C10	0.0420 (7)	0.0496 (7)	0.0294 (6)	−0.0030 (5)	0.0146 (5)	0.0032 (5)
C13	0.0479 (8)	0.0687 (10)	0.0417 (7)	0.0176 (7)	0.0235 (6)	0.0123 (7)
C2	0.0555 (8)	0.0499 (8)	0.0300 (6)	−0.0003 (6)	0.0147 (6)	0.0052 (5)
N2	0.0583 (8)	0.0716 (9)	0.0339 (6)	−0.0037 (7)	0.0218 (5)	0.0014 (6)
C1	0.0629 (9)	0.0392 (7)	0.0427 (7)	0.0011 (6)	0.0219 (7)	−0.0044 (6)
C11	0.0521 (9)	0.0833 (12)	0.0349 (7)	0.0148 (8)	0.0118 (6)	0.0209 (7)
O6	0.1211 (13)	0.1419 (14)	0.0516 (7)	0.0380 (11)	0.0524 (8)	0.0415 (8)
C12	0.0509 (9)	0.0965 (13)	0.0529 (9)	0.0351 (9)	0.0197 (7)	0.0271 (9)

Geometric parameters (Å, º) top

O1—C4	1.3560 (14)	C7—H7	0.9300
O1—C3	1.4441 (14)	O5—N2	1.2183 (18)
O3—C4	1.2147 (14)	C6—C5	1.4524 (16)
O2—C6	1.3580 (15)	C10—C11	1.370 (2)
O2—C3	1.4348 (15)	C10—N2	1.4665 (17)
C4—C5	1.4401 (17)	C13—C12	1.383 (2)
N1—C7	1.3219 (15)	C13—H13	0.9300
N1—C8	1.4190 (15)	C2—H2A	0.9600
N1—H1	0.882 (16)	C2—H2B	0.9600
C8—C9	1.3800 (17)	C2—H2C	0.9600
C8—C13	1.3875 (18)	N2—O6	1.2164 (17)
C9—C10	1.3802 (17)	C1—H1A	0.9600
C9—H9	0.9300	C1—H1B	0.9600
C3—C1	1.5030 (18)	C1—H1C	0.9600
C3—C2	1.5053 (17)	C11—C12	1.378 (2)
O4—C6	1.2092 (16)	C11—H11	0.9300
C7—C5	1.3754 (16)	C12—H12	0.9300

C4—O1—C3	117.92 (9)	C4—C5—C6	119.70 (10)
C6—O2—C3	117.84 (9)	C11—C10—C9	123.24 (12)
O3—C4—O1	118.31 (11)	C11—C10—N2	118.87 (12)
O3—C4—C5	124.71 (11)	C9—C10—N2	117.88 (12)
O1—C4—C5	116.96 (10)	C12—C13—C8	119.52 (13)
C7—N1—C8	124.04 (10)	C12—C13—H13	120.2
C7—N1—H1	119.2 (10)	C8—C13—H13	120.2
C8—N1—H1	116.7 (10)	C3—C2—H2A	109.5
C9—C8—C13	120.26 (11)	C3—C2—H2B	109.5
C9—C8—N1	118.62 (11)	H2A—C2—H2B	109.5
C13—C8—N1	121.12 (11)	C3—C2—H2C	109.5
C8—C9—C10	118.11 (11)	H2A—C2—H2C	109.5
C8—C9—H9	120.9	H2B—C2—H2C	109.5
C10—C9—H9	120.9	O6—N2—O5	123.59 (14)
O2—C3—O1	109.91 (9)	O6—N2—C10	117.94 (14)
O2—C3—C1	110.44 (11)	O5—N2—C10	118.46 (12)
O1—C3—C1	110.45 (10)	C3—C1—H1A	109.5
O2—C3—C2	106.13 (10)	C3—C1—H1B	109.5
O1—C3—C2	106.25 (10)	H1A—C1—H1B	109.5
C1—C3—C2	113.48 (11)	C3—C1—H1C	109.5
N1—C7—C5	126.51 (11)	H1A—C1—H1C	109.5
N1—C7—H7	116.7	H1B—C1—H1C	109.5
C5—C7—H7	116.7	C10—C11—C12	117.54 (13)
O4—C6—O2	118.33 (11)	C10—C11—H11	121.2
O4—C6—C5	125.30 (12)	C12—C11—H11	121.2
O2—C6—C5	116.25 (10)	C11—C12—C13	121.26 (14)
C7—C5—C4	122.25 (10)	C11—C12—H12	119.4
C7—C5—C6	117.66 (11)	C13—C12—H12	119.4

C3—O1—C4—O3	163.48 (11)	O3—C4—C5—C6	165.88 (12)
C3—O1—C4—C5	−18.46 (15)	O1—C4—C5—C6	−12.04 (17)
C7—N1—C8—C9	−149.73 (12)	O4—C6—C5—C7	7.2 (2)
C7—N1—C8—C13	30.4 (2)	O2—C6—C5—C7	−176.78 (11)
C13—C8—C9—C10	1.64 (19)	O4—C6—C5—C4	−165.75 (14)
N1—C8—C9—C10	−178.26 (11)	O2—C6—C5—C4	10.23 (18)
C6—O2—C3—O1	−50.49 (14)	C8—C9—C10—C11	−1.1 (2)
C6—O2—C3—C1	71.61 (13)	C8—C9—C10—N2	179.15 (11)
C6—O2—C3—C2	−164.99 (10)	C9—C8—C13—C12	−0.1 (2)
C4—O1—C3—O2	48.46 (13)	N1—C8—C13—C12	179.74 (15)
C4—O1—C3—C1	−73.64 (14)	C11—C10—N2—O6	22.6 (2)
C4—O1—C3—C2	162.88 (10)	C9—C10—N2—O6	−157.58 (15)
C8—N1—C7—C5	−179.14 (12)	C11—C10—N2—O5	−158.17 (16)
C3—O2—C6—O4	−161.51 (12)	C9—C10—N2—O5	21.6 (2)
C3—O2—C6—C5	22.23 (16)	C9—C10—C11—C12	−1.0 (3)
N1—C7—C5—C4	1.6 (2)	N2—C10—C11—C12	178.78 (16)
N1—C7—C5—C6	−171.23 (12)	C10—C11—C12—C13	2.5 (3)
O3—C4—C5—C7	−6.8 (2)	C8—C13—C12—C11	−2.0 (3)
O1—C4—C5—C7	175.30 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.882 (16)	2.150 (15)	2.7705 (14)	126.8 (13)
N1—H1···O3ⁱ	0.882 (16)	2.308 (16)	3.1101 (14)	151.2 (13)
C7—H7···O4	0.93	2.48	2.8026 (18)	101
C7—H7···O4ⁱⁱ	0.93	2.58	3.4527 (18)	156
C11—H11···O4ⁱⁱⁱ	0.93	2.39	3.242 (2)	152
C13—H13···O4ⁱⁱ	0.93	2.36	3.205 (2)	151

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y, −z+2; (iii) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₂O₆
M_r	292.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	11.7900 (13), 8.7699 (9), 14.0614 (15)
β (°)	113.864 (1)
V (Å³)	1329.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8116, 3052, 2572
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.101, 1.05
No. of reflections	3052
No. of parameters	197
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.882 (16)	2.150 (15)	2.7705 (14)	126.8 (13)
N1—H1···O3ⁱ	0.882 (16)	2.308 (16)	3.1101 (14)	151.2 (13)
C7—H7···O4	0.93	2.48	2.8026 (18)	101
C7—H7···O4ⁱⁱ	0.93	2.58	3.4527 (18)	156
C11—H11···O4ⁱⁱⁱ	0.93	2.39	3.242 (2)	152
C13—H13···O4ⁱⁱ	0.93	2.36	3.205 (2)	151

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y, −z+2; (iii) −x, y+1/2, −z+3/2.

Acknowledgements

This research was supported financially by the State Key Laboratory of Drug Research (Shanghai Institute of Materia Medica, Chinese Academy of Sciences).

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