5-(Biphenyl-4-yl)-3-(3-meth­oxy­benzyl­idene)furan-2(3H)-one

Jerry P Jasinski; James A Golen; A S Dayananda; H S Yathirajan; Ravinesh Mishra

doi:10.1107/S1600536811031588

. 2011 Aug 11;67(Pt 9):o2294–o2295. doi: 10.1107/S1600536811031588

5-(Biphenyl-4-yl)-3-(3-methoxybenzylidene)furan-2(3H)-one

Jerry P Jasinski ^a,^*, James A Golen ^a, A S Dayananda ^b, H S Yathirajan ^b, Ravinesh Mishra ^c

PMCID: PMC3200951 PMID: 22065726

Abstract

In the title compound, C₂₄H₁₈O₃, the dihedral angles between the mean planes of the five-membered furan ring and the methoxy-substituted benzene and the adjacent and outer biphenyl benzene rings are 2.43 (7), 4.48 (7) and 30.47 (8)°, respectively. The crystal packing is stabilized by weak C—H⋯O and C—H⋯π intermolecular hydrogen bonds and π–π stacking interactions [centroid–centroid distances = 3.8752 (8) and 3.8331 (8) Å].

Related literature

For potential anti-ulcer agents containing a furanone structure, see: Felman et al. (1992 ▶). For the role of furanones in the biochemical processes of the human body, see: Rappai et al. (2009 ▶). For the gastrointestinal toxicity of acidic non-steroidal anti-inflammatory drugs (NSAIDs), see: Husain et al. (2010 ▶). For gastrointestinal side effects of NSAIDS, see: Cioli et al. (1979 ▶). For biologically active five-membered heterocyles such as butenolides and pyrrolones, see: Husain et al. (2005 ▶); Khan & Husain (2002 ▶). For oxadiazoles and triazoles, see: Husain & Ajmal (2009 ▶); Hashem et al. (2007 ▶). For a related structure, see: Burke et al. (2000 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₄H₁₈O₃
M _r = 354.38
Monoclinic,
a = 19.8766 (8) Å
b = 6.9914 (3) Å
c = 13.2603 (6) Å
β = 107.735 (4)°
V = 1755.15 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 170 K
0.22 × 0.22 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.981, T _max = 0.990
19756 measured reflections
4534 independent reflections
3310 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.143
S = 1.01
4534 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031588/ci5197sup1.cif

e-67-o2294-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031588/ci5197Isup2.hkl

e-67-o2294-Isup2.hkl^{(222.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811031588/ci5197Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O3ⁱ	0.95	2.56	3.3358 (18)	138
C5—H5A⋯Cg1ⁱⁱ	0.95	2.69	3.4762 (16)	141

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

Acknowledgments

ASD thanks the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

Certain drugs containing a furanone structure were potential anti-ulcer agents because they did not irritate the lining of the stomach (Felman et al., 1992). Their occurrence in nature has been exploited in the pharmaceutical industry because of their unusual biological activities, such as anti-ulcer and anti-cancer treatments. The antitumor activity of several analogs of furanones was evaluated using both in vivo and in vitro methods on mice, where oral adminstration showed a relative decrease in tumor growth. In an effort to create more efficient drugs, scientists began to explore the role of furanones in the biochemical processes of the human body (Rappai et al., 2009). The gastrointestinal toxicity of acidic non-steroidal anti- inflammatory drugs (NSAIDs) is one of the most challenging problems in medicinal chemistry (Husain et al., 2010). NSAIDs form a class of therapeutic agents that are most widely used world over because of their antiinflammatory, analgesic and antipyretic effects. Aroylpropionic acids and furanones are effective anti-inflammatory agents and some of them are available in the market, however, they are associated with gastrointestinal side effects; a common feature of NSAIDs (Cioli et al., 1979). Studies suggest that the direct tissue contact of these agents plays an important role in the production of side effects and the reported literature confirms that gastrointestinal side effects of aroylpropionic acids are due to the presence of the free carboxylic group in the parent drug. This free carboxylic group, therefore, has been converted to the furanone ring to get a compound free from GIT side effects. Furanones and b\-aroylpropionic acids are important intermediates in heterocyclic chemistry and have been used for the synthesis of various biologically active five-membered heterocyles such as butenolides, pyrrolones (Husain et al., 2005; Khan et al., 2002) oxadiazoles (Husain et al., 2009) and triazoles (Hashem et al., 2007). The crystal structure study of a related compound, (E)-6-methoxy-3-( -methoxybenzylidene)benzo[b]furan-2(3H)-one, at 173 K is reported (Burke et al., 2000). In view of the importance of the title compound, (I), this paper reports its crystal structure.

In the title molecule, the dihedral angles between the mean planes of the five-menbered furan ring and the methoxy substituted benzene and biphenyl benzene rings are 2.43 (7)°, 4.48 (7)°, and 30.47 (8)°, respectively (Fig. 1). Bond lengths are in normal ranges (Allen et al., 1987). The crystal packing is stabiized by weak C—H···O and C—H···π intermolecular hydrogen bonds and π-π stacking (Table 2) interactions (Fig. 2).

Experimental

A solution of 3-(4-phenylbenzoyl)propionic acid (0.71 g, 3 mmol) and 3-methoxybenzaldehyde (0.45 g, 3 mmol) in a acetic anhydride (5 ml) with triethylamine (3–4 drops) was refluxed for 5–6 hrs on a water bath under anhydrous conditions. After completion of the reaction, the contents were poured into crushed ice in small portions while stirring. A solid mass separated out, which was filtered, washed with water and crystallized from 2-butanone to get X-ray quality crystals (m.p. 411–413 K).