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Structure and Antibacterial Activity of 3-(3,4-Dimethoxyphenyl)furan-2(5H)-ones

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Abstract

Crystalline hydrate of the title compound (5), C19H26N2O5·2(H2O), was structurally characterized by single crystal X-ray diffraction. It crystallizes in monoclinic system space group P 21/c with a = 7.3987(7) Å, b = 17.8691(16) Å, c = 17.0022(13) Å, β = 112.944(3)°, V = 2070.0(3) Å3, Z = 4, R 1 = 0.0592, wR 2 = 0.1016, and T = 298(2) K. The X-ray structure determination revealed that the center furanone ring is nearly coplanar with 3,4-dimethoxybenzene ring, making a dihedral angle of 0.860(69)°. Two kinds of centrosymmetric tetramers characterized by graph-set motifs of R 87 (36) and R 64 (32) are formed through O–H···O, O–H···N and C–H···O hydrogen bonding interactions, which generate a sheet of edge-fused rings parallel to the (011) plane. These sheets are further linked into a three dimensional network by C–H···π interactions. Nine 3-(3,4-dimethoxyphenyl)furan-2(5H)-ones were synthesized and fully characterized by elemental analysis, MS and 1H NMR. All of them were evaluated for antimicrobial activities against three Gram-positive organisms and a Gram-negative organism, and compound 5 was the most active against Staphylococcus aureus ATCC 25923.

Graphical Abstract

Two kinds of centrosymmetric tetramers characterized by graph-set motifs of R 87 (36) and R 64 (32) are formed through O–H···O, O–H···N and C–H···O hydrogen bonding interactions, which generate a sheet of edge-fused rings parallel to the (011) plane.

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Acknowledgments

The work was financed by the Planned Science and Technology Project of Hunan Province, China (grant No. 2011FJ3056), by Hunan Provincial Natural Science Foundation of China (grant No. 11JJ3113), by the Key Laboratory of Ecotourism’s Application Technology, Hunan Province (grant No. JDSTLY 01103), by a grant from National Natural Science Foundation (Youth Science Funds, No. 31100421) of China and by aid program for Science and Technology Innovative Research Team (Chemicals of Forestry Resources and Development of Forest Products) in Higher Educational Institutions of Hunan Province.

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Authors and Affiliations

  1. School of Chemistry & Chemical Engineering, Key Laboratory of Ecotourism’s Application Technology, Hunan Province and Key Laboratory of Hunan Forest Products and Chemical Industry Engineering, Jishou University, Jishou, 416000, People’s Republic of China

    Zhu-Ping Xiao, Li-Cheng Yi, Tian-Fang Yi, Kai-Shuang Xiang, Ze-Jun Huang & Hai-Liang Zhu

  2. State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, 210093, People’s Republic of China

    Hai-Liang Zhu

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  1. Zhu-Ping Xiao
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  2. Li-Cheng Yi
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  3. Tian-Fang Yi
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  4. Kai-Shuang Xiang
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  5. Ze-Jun Huang
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Correspondence to Zhu-Ping Xiao or Hai-Liang Zhu.

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Xiao, ZP., Yi, LC., Yi, TF. et al. Structure and Antibacterial Activity of 3-(3,4-Dimethoxyphenyl)furan-2(5H)-ones. J Chem Crystallogr 42, 323–329 (2012). https://doi.org/10.1007/s10870-011-0246-9

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  • DOI: https://doi.org/10.1007/s10870-011-0246-9

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