Diethyl 2-[(3,5-dimethyl-1H-pyrazol-1-yl)(4-meth­oxy­phen­yl)meth­yl]propane­dioate

Ihssan Meskini; Maria Daoudi; Jean-Claude Daran; Abdelali Kerbal; Hafid Zouihri

doi:10.1107/S1600536810025572

. 2010 Jul 10;66(Pt 8):o1965. doi: 10.1107/S1600536810025572

Diethyl 2-[(3,5-dimethyl-1H-pyrazol-1-yl)(4-methoxyphenyl)methyl]propanedioate

Ihssan Meskini ^a, Maria Daoudi ^a,^*, Jean-Claude Daran ^b, Abdelali Kerbal ^a, Hafid Zouihri ^c

PMCID: PMC3007575 PMID: 21588286

Abstract

The title compound, C₂₀H₂₆N₂O₅, was prepared in good yield (76%) through condensation of diethyl (4-methoxybenzyl)propanedioate with 3,5-dimethyl-1H-pyrazole. The dihedral between the benzene and pyrazole rings is 83.96 (10)°. The crystal packing is stabilized by a C—H⋯O interaction, which links the molecules into centrosymmetric dimers.

Related literature

For related compounds displaying biological activity, see: Dayam et al. (2007 ▶); Patil et al. (2007 ▶); Ramkumar et al. (2008 ▶); Sechi et al. (2009 ▶) & Zeng et al. (2008 ▶). For the synthetic procedure, see: Pommier & Neamati (2006 ▶).

Experimental

Crystal data

C₂₀H₂₆N₂O₅
M _r = 374.43
Monoclinic,
a = 11.9618 (3) Å
b = 7.9681 (2) Å
c = 21.1269 (6) Å
β = 96.504 (1)°
V = 2000.70 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.23 × 0.17 × 0.14 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer
18616 measured reflections
3921 independent reflections
3177 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.154
S = 1.05
3921 reflections
249 parameters
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025572/bt5280sup1.cif

e-66-o1965-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025572/bt5280Isup2.hkl

e-66-o1965-Isup2.hkl^{(192.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 3

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2ⁱ	0.93	2.51	3.358 (3)	152

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by grants from Project PGR-UMP-BH-2005, the Centre National de Recherche Scientifique, CNRS (France), the Centre National pour la Recherche Scientifique et Technique, CNRST (Morocco), and the CURI (Morocco).

supplementary crystallographic information

Comment

For the rational design of new HIV-1 Integrase (H—I) inhibitors, one validated target for chemotherapeutic intervention (Dayam et al., 2007), is fundamentally based on intermolecular coordination between H—I / chemical inhibitor / metals (Mg⁺² and Mn⁺², co-factors of the enzyme), leading to the formation of bimetallic complexes (Zeng et al., 2008; Sechi et al., 2009). Thereby, several bimetallic metal complexes, in many cases exploring the known-well polydentate ligands, appear in this scenario as the most promising concept to be employed in either enzyme / drug interaction or electron transfer process, in the last case involving the biological oxygen transfer (Sechi et al., 2009; Ramkumar et al., 2008). Another exciting example of application for such polydentate ligands involves the synergic water activation, that occurs via the so-called -remote metallic atoms. Such organometallic compounds are structurally deemed to promote or block the H—I activity (Zeng et al., 2008).

In the molecule of the title compound (Fig.1), the dihedral angle between the planes of the pheny and the pyrazol ring is 83.96 (10)°.

Experimental

To a solution of the diethyl (4-methoxybenzyl)propanedioate (5 mmol) in water (20 ml) was added the 3,5-dimethyl-1H-pyrazole (6 mmol) and the mixture and the stirring was continued at room temperature until the complete consume of the starting material. After removing solvent, the crude products were dissolved in diethyl ether (2x40 ml) and washed with water until the pH became neutral. The organic solvent was dried with sodium sulfate and then evaporated to give the pure compound (I) with 76% yield.. White crystals are obtained by recrystallization in ether/hexane (2/1).

Suitable single-crystal of malonate derivative (I) was obtained by recrystallization from ethanol. A white-transparent crystal was mounted on a glass fibre.