Ethyl 2-[4-(benzyloxy)anilino]-4-oxo-4,5-dihydro­furan-3-carboxyl­ate

S Nirmala; R Murugan; E Theboral Sugi Kamala; L Sudha; S Sriman Narayanan

doi:10.1107/S1600536808035988

. 2008 Nov 13;64(Pt 12):o2315. doi: 10.1107/S1600536808035988

Ethyl 2-[4-(benzyloxy)anilino]-4-oxo-4,5-dihydrofuran-3-carboxylate

S Nirmala ^a, R Murugan ^b, E Theboral Sugi Kamala ^a, L Sudha ^c,^*, S Sriman Narayanan ^b

PMCID: PMC2960036 PMID: 21581291

Abstract

In the title compound, C₂₀H₁₉NO₅, the dihydrofuran ring is almost planar [maximum deviation of 0.021 (2)°] and makes dihedral angles of 28.1 (7) and 54.5 (5)° with the benzyl and phenylamino rings, respectively. The molecular packing is stabilized by intramolecular N—H⋯O hydrogen bonds and intermolecular C—H⋯O interactions.

Related literature

For background on the development of effective and tolerable therapeutic options for cervical cancer, see: Huang et al. (2007 ▶); Lu et al. (2008 ▶). For the analysis of apoptosis induced by dihydrofuran carboxylate compounds, see: Chen et al. (2006 ▶); Lin et al. (2006 ▶); Zhang & Wei (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Erdsack et al. (2007 ▶).

Experimental

Crystal data

C₂₀H₁₉NO₅
M _r = 353.36
Triclinic,
a = 9.1315 (3) Å
b = 10.4040 (3) Å
c = 11.1162 (4) Å
α = 84.848 (2)°
β = 66.436 (2)°
γ = 64.121 (2)°
V = 866.34 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 (2) K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (Blessing, 1995 ▶) T _min = 0.976, T _max = 0.981
22596 measured reflections
5349 independent reflections
3665 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.163
S = 1.03
5349 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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: PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035988/bq2103sup1.cif

e-64-o2315-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035988/bq2103Isup2.hkl

e-64-o2315-Isup2.hkl^{(256.6KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86	2.12	2.7485 (15)	129
C6—H6⋯O3ⁱ	0.93	2.51	3.3951 (18)	160
C17—H17⋯O4ⁱⁱ	0.93	2.58	3.465 (2)	160

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

SN thanks Professor M. N. Ponnuswamy, Department of Crystallography and Biophysics, University of Madras, India, for his guidance and valuable suggestions, and also the Management of SRM, India, for their support.

supplementary crystallographic information

Comment

Human cervical cancer is potentially lethal, and therefore the development of effective and tolerable therapeutic options is vital (Huang et al., 2007; Lu et al., 2008). Dihydrofuran carboxylate compounds induced morphological changes and cytotoxicity in a dose - dependent manner. Dihydrofuran carboxylate compounds induced apoptosis which was analyzed by flow cytometric methods and confirmed by DAPI staining and DNA fragmentation analyzed by DNA gel electrophoresis (Chen et al., 2006; Lin et al., 2006; Zhang & Wei, 2007). In view of this medicinal importance, an X-ray study of the title compound, (I), was carried out.

An ORTEP (Farrugia,1997) plot of the molecule is shown in Fig. 1. The bond lengths in (I) show normal values (Allen et al., 1987) and are comparable to the related structure (Erdsack et al., 2007). The dihydrofuran ring (O2/C1—C4) is planar with a maximum deviation of -0.021 (2)° for C3 from the least square plane defined by all non hydrogen atoms in the molecule. The dihydrofuran ring makes dihedral angles of 28.1 (7)° and 54.5 (5)°, respectively, with the benzyl ring (C12—C17) and phenylamino ring (C5—C10), whereas the benzyl and phenylamino rings are oriented at an angle of 78.6 (6)° with respect to each other.

The crystal structure is stabilized by intramolecular N—H···O interactions. In addition to the van der Waals interactions, the molecular packing in the crystal is also stabilized by intermolecular C—H···O interactions (Table 1, Fig. 2).

Experimental

1.0 mol of 4-(benzyloxy) aniline (1.0 g) and 1.0 mol of ethyl 2-chloro-4- oxo-4,5-dihydrofuran-3-carboxylate (0.9 g) was allowed to stir in 10 ml of dichloromethane which contains 0.5 ml of triethylamine at room temperature for about 8 hrs. The completion of the reaction was monitored by TLC. After the completion of reaction the crude solid was filtered and then recrystallized in ethanol.