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Syntheses, Crystal Structures and Antibacterial Activities of Two Antipyrine Derivatives

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Abstract

Two new antipyrine derivatives, 4-{[1-(5-bromo-2-methoxyphenyl)methylidene]amino}-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one (C19H18BrN3O2, 1) and 4-{[1-(2-hydroxy-3-ethoxyphenyl)methylidene]amino}-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one (C20H21N3O3, 2), were synthesized and structurally characterized by elemental analysis, IR and single crystal X-ray diffractions. Compound 1 crystallizes in the monoclinic space group P21/n with unit cell dimensions a = 6.987(1) Å, b = 27.930(2) Å, c = 9.483(1) Å, β = 109.36(2)°, V = 1745.9(4) Å3, Z = 4, R 1 = 0.0430, and wR 2 = 0.0870. Compound 2 crystallizes in the monoclinic space group P21/c with unit cell dimensions a = 19.523(2) Å, b = 7.466(1) Å, c = 12.954(2) Å, β = 108.797(1)°, V = 1787.5(4) Å3, Z = 4, R 1 = 0.0421, and wR 2 = 0.1032. X-ray structure determinations revealed that the molecules of both compounds display trans configurations about the C=N double bonds. In the crystal structures, molecules are linked together by intermolecular C–H···O hydrogen bonds. Both compounds show strong antibacterial activities.

Graphical Abstract

Two new antipyrine derivatives were synthesized and structurally characterized. Both compounds show strong antibacterial activities.

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  1. Department of Chemistry, Baicheng Normal College, Baicheng, 137000, People’s Republic of China

    Xinyou Zhang

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  1. Xinyou Zhang
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Correspondence to Xinyou Zhang.

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Zhang, X. Syntheses, Crystal Structures and Antibacterial Activities of Two Antipyrine Derivatives. J Chem Crystallogr 41, 1044–1048 (2011). https://doi.org/10.1007/s10870-011-0042-6

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  • DOI: https://doi.org/10.1007/s10870-011-0042-6

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