2-(4-Bromophenyl)-2-oxoethyl 4-bromobenzoate

Fun, Hoong‐Kun; Arshad, Suhana; Garudachari, B.; Isloor, Arun M.; Satyanarayan, M. N.

doi:10.1107/s1600536811020654

Acta Cryst E

2011

DOI: 10.1107/s1600536811020654

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2-(4-Bromophenyl)-2-oxoethyl 4-bromobenzoate

Hoong‐Kun Fun

Suhana Arshad

B. Garudachari

et al.

Abstract: The asymmetric unit of the title compound, C15H10Br2O3, consists of three crystallographically independent molecules (A, B and C). The phenyl rings in molecules A, B and C make dihedral angles of 6.1 (3), 3.2 (2) and 54.6 (2)° to each other, respectively. In the crystal, molecules are linked into two-dimensional layers parallel to the ab plane by intermolecular C—H⋯O hydrogen bonds. The crystal structure is further stabilized by C—H⋯π interactions. The studied crystal is an inversion twin, the refined rat… Show more

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Cited by 4 publications

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Crystal structure and Hirshfeld surface analysis of 2-(4-nitrophenyl)-2-oxoethyl picolinate

Murthy¹,

Kumar²,

Naveen³

et al. 2019

Acta Cryst E

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2-(4-Nitrophenyl)-2-oxoethyl picolinate was synthesized under mild conditions. The chemical and molecular structure was confirmed by single-crystal X-ray diffraction studies. The molecules are related by inversion into centrosymmetric dimers via weak C—H⋯O intermolecular interactions, and further strengthened by weak π–π interactions. A quantification of the intermolecular contacts in the crystal were estimated using Hirshfeld surface analysis and two-dimensional fingerprint plots.

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Crystal structure and Hirshfeld surface analysis of 2-(4-nitrophenyl)-2-oxoethyl picolinate

Murthy¹,

Kumar²,

Naveen³

et al. 2019

Acta Cryst E

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Novel biphenyl ester derivatives as tyrosinase inhibitors: Synthesis, crystallographic, spectral analysis and molecular docking studies

et al. 2017

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Biphenyl-based compounds are clinically important for the treatments of hypertension and inflammatory, while many more are under development for pharmaceutical uses. In the present study, a series of 2-([1,1'-biphenyl]-4-yl)-2-oxoethyl benzoates, 2(a-q), and 2-([1,1'-biphenyl]-4-yl)-2-oxoethyl pyridinecarboxylate, 2(r-s) were synthesized by reacting 1-([1,1'-biphenyl]-4-yl)-2-bromoethan-1-one with various carboxylic acids using potassium carbonate in dimethylformamide at ambient temperature. Single-crystal X-ray diffraction studies revealed a more closely packed crystal structure can be produced by introduction of biphenyl moiety. Five of the compounds among the reported series exhibited significant anti-tyrosinase activities, in which 2p, 2r and 2s displayed good inhibitions which are comparable to standard inhibitor kojic acid at concentrations of 100 and 250 μg/mL. The inhibitory effects of these active compounds were further confirmed by computational molecular docking studies and the results revealed the primary binding site is active-site entrance instead of inner copper binding site which acted as the secondary binding site.

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Conformational studies of 2-(4-bromophenyl)-2-oxoethyl benzoates

Kumar

Chia

Ooi

et al. 2014

Zeitschrift Für Kristallographie - Crystalline Materials

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Phenacyl benzoates possess commercial importance due to their various applications in the fields of synthetic and photochemistry, such as photosensitive blocking groups owing to their ease of cleavage under mild conditions. In the present study, a series of ten new 2-(4-bromophenyl)-2-oxoethyl benzoates 2(a-j), with the general formula Br(C 6 H 4 )COCH 2 OCO(C 6 H 5Àn X n ), X ¼ Cl, NO 2 or NH 2 , and n ¼ 1 or 2, have been synthesized by reacting 4-bromophenacyl bromide with various substituted benzoic acids using potassium carbonate in DMF medium at room temperature. These reactions proceeded with ease under mild conditions producing high purity products in good yield. Each product was characterized by mass spectra, elemental analysis and melting points, its 3D structure was confirmed by single-crystal X-ray diffraction studies. The X-ray 3D structures showed the flexibility of the C(¼O)-O-C-C(¼O) connecting bridge in which 7 out of 10 compounds tend to form a torsion angle in the range of 70 to 91°, whereas the rest are slightly twisted with a torsion angles of À160, 163, 176 and 178°. Their molecular conformations are in good agreement with another 22 related structures. These synthesized compounds were screened for their abilities for DPPH radical scavenging and ferric reducing anti-oxidant power. The results indicate that these compounds displayed mild anti-oxidant ability when compared to the standard anti-oxidant BHT.

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2-(4-Bromophenyl)-2-oxoethyl 4-bromobenzoate

Cited by 4 publications

References 12 publications

Crystal structure and Hirshfeld surface analysis of 2-(4-nitrophenyl)-2-oxoethyl picolinate

Crystal structure and Hirshfeld surface analysis of 2-(4-nitrophenyl)-2-oxoethyl picolinate

Novel biphenyl ester derivatives as tyrosinase inhibitors: Synthesis, crystallographic, spectral analysis and molecular docking studies

Conformational studies of 2-(4-bromophenyl)-2-oxoethyl benzoates

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