Structure and Antibacterial Activity of 3-(3,4-Dimethoxyphenyl)furan-2(5<Emphasis Type="Italic">H</Emphasis>)-ones |
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Authors: | Zhu-Ping Xiao Li-Cheng Yi Tian-Fang Yi Kai-Shuang Xiang Ze-Jun Huang Hai-Liang Zhu |
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Institution: | (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;(2) State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, 210093, People’s Republic of China |
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Abstract: | 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) ?, b = 17.8691(16) ?, c = 17.0022(13) ?, β = 112.944(3)°, V = 2070.0(3) ?3, 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
78(36) and R
46(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. |
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