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

Abstract

Crystalline hydrate of the title compound (5), C 19 H 26 N 2 O 5 Á2(H 2 O), 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 , b = 112.944(3)°, V = 2070.0(3) Å 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 7 8 (36) and R 4 6 (32) are formed through O-HÁÁÁO, O-HÁÁÁN and C-HÁÁÁO 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-HÁÁÁp interactions. Nine 3-(3,4-dimethoxyphenyl)furan-2(5H)-ones were synthesized and fully characterized by elemental analysis, MS and 1 H 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.

Synthesis, Characterization, Cytotoxicity, and Antibacterial Properties of trans‐γ‐Halo‐δ‐lactones

“…[1] Lactoned erivatives also occur in microorganisms and animals, [2] fulfilling an umber of different functions. The biological activities, such as cytostatic, [3][4][5][6][7][8] antibacterial, [9][10][11][12] antiviral [13][14][15][16][17] or antifungal [18][19][20] activities,h ave applications in medicine. Sensory properties make them useful in the production of cosmetics and in the food industry,w here they are responsible for the smell and taste of many products.…”