Benzofuranyl Esters: Synthesis, Crystal Structure Determination, Antimicrobial and Antioxidant Activities
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. X-ray Crystal Structure Description
Compound | 4a | 4b | 4c | 4d | 4e |
---|---|---|---|---|---|
CCDC Deposition Number | 1,037,756 | 1,037,759 | 1,037,762 | 1,037,763 | 1,037,764 |
Molecular Formula | C17H12O4 | C17H11ClO4 | C18H14O4 | C18H14O5 | C17H11NO6 |
Molecular Weight | 280.27 | 314.71 | 294.29 | 310.29 | 325.27 |
Crystal System | Monoclinic | Monoclinic | Monoclinic | Triclinic | Triclinic |
Space Group | P21/n | C2/c | P21/n | ||
a (Å) | 10.2230(9) | 33.483(5) | 12.5266(13) | 6.9335(6) | 6.5424(10) |
b (Å) | 8.4353(7) | 5.3687(8) | 6.7689(7) | 8.4724(7) | 13.197(2) |
c (Å) | 16.1205(15) | 26.404(4) | 18.0335(19) | 12.8702(11) | 16.973(3) |
α (°) | 90 | 90 | 90 | 103.539(2) | 79.694(3) |
β (°) | 98.300(2) | 114.833(3) | 108.165(2) | 95.789(2) | 87.211(3) |
γ (°) | 90 | 90 | 90 | 92.664(2) | 85.715(3) |
V (Å3) | 1375.6(2) | 4307.6(10) | 1452.9(3) | 729.36(11) | 1436.9(4) |
Z | 4 | 12 | 4 | 2 | 4 |
Dcalc (g·cm−3) | 1.353 | 1.456 | 1.345 | 1.413 | 1.504 |
Crystal Dimension (mm) | 0.25 × 0.36 × 0.48 | 0.08 × 0.17 × 0.46 | 0.14 × 0.24 × 0.46 | 0.20 × 0.27 × 0.41 | 0.12 × 0.20 × 0.41 |
µ (mm−1) | 0.10 | 0.28 | 0.10 | 0.10 | 0.12 |
Tmin/Tmax | 0.901/0.976 | 0.857/0.977 | 0.903/0.987 | 0.899/0.980 | 0.903/0.986 |
Reflections Measured | 15,170 | 17,994 | 16,236 | 14,866 | 37,178 |
Indices Range (h, k, l) | −14, 9; | −40, 40; | −17, 16; | −9, 9; | −7, 7; |
−9, 11; | −6, 6; | −9, 9; | −11, 11; | −15, 15; | |
−22, 22 | −32, 32 | −25, 24 | −18, 18 | −20, 20 | |
θ Limit (°) | 2.2–30.2 | 1.7–26.0 | 1.8–30.0 | 1.6–30.2 | 1.6–25.0 |
Unique Reflections | 4037 | 4235 | 4234 | 4283 | 4946 |
Observed Reflections (I > 2σ(I)) | 2630 | 2044 | 2835 | 3078 | 3889 |
Parameters | 190 | 397 | 200 | 209 | 433 |
Goodness of Fit on F2 | 1.04 | 0.98 | 1.03 | 1.07 | 1.11 |
R1,wR2 [I > 2σ(I)] | 0.047, 0.162 | 0.044, 0.143 | 0.045, 0.148 | 0.045, 0.149 | 0.065, 0.216 |
Compound | O1–C8–C9–O3 (τ1,°) | C9–C10–O2–C11 (τ2,°) | O2–C11–C12–C13 (τ3,°) |
---|---|---|---|
4a | −176.92(14) | 75.19(17) | 171.53(13) |
4b | 5.3(4), −175(2) | 162.5(2), −70.2(13) | −176.7(2), −172(2) |
4c | −3.5(2) | 78.36(16) | −171.25(12) |
4d | −2.62(19) | 79.49(15) | −169.34(11) |
4e | 7.2(4), 2.5(4) | 177.4(2), 179.6(3) | −175.4(3), −175.6(3) |
2.3. Antimicrobial Activities of the Synthesized Compound
Compound | Gram Negative | Gram Positive | Yeast | |||||
---|---|---|---|---|---|---|---|---|
Escherichia coli ATCC 25922 | Klebsiella pneumoniae ATCC 13883 | Pseudomonas aeruginosa ATCC 27853 | Salmonella typhimurium ATCC 14028 | Bacillus licheniformis ATCC 12759 | Streptococcus mutans ATCC 25175 | Staphylococcus aureus ATCC 700699 | Candida albicans ATCC 10231 | |
4a | 1000 | 1000 | 1000 | 1000 | 1000 | 1000 | 1000 | 1000 |
4b | - | - | - | - | - | - | - | - |
4c | 500 | 500 | 500 | 500 | - | 500 | 500 | 500 |
4d | 500 | 500 | 500 | 250 | 250 | 250 | 250 | 250 |
4e | 250 | 250 | 250 | 125 | 250 | 125 | 250 | 125 |
Tetracycline | 0.977 | 1.953 | 7.813 | 0.977 | 1.953 | 0.244 | 31.25 | 0.122 |
2.4. Antioxidant Activities of the Synthesized Compound
3. Experimental Section
3.1. Instrumentation
3.2. X-ray Diffraction Analysis
3.3. Synthesis
3.3.1. Synthesis of 1-(Benzofuran-2-yl)ethanone (2) and -(Benzofuran-2-yl)-2-bromoethan-1-one (3)
3.3.2. General Procedure for the Synthesis of 2‐(1‐Benzofuran‐2‐yl)‐2‐oxoethyl 4 (Unsubstituted/substituted)benzoates 4(a–e)
3.4. Antimicrobial Activities
3.5. Antioxidant Activities
3.5.1. Diphenyl-2-picrylhydrazyl (DPPH) Radical Scavenging Assay
3.5.2. Ferric Reducing Antioxidant Power (FRAP) Assay
3.5.3. Metal Chelating (MC) Assay
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Kumar, C.S.C.; Then, L.Y.; Chia, T.S.; Chandraju, S.; Win, Y.-F.; Sulaiman, S.F.; Hashim, N.S.; Ooi, K.L.; Quah, C.K.; Fun, H.-K. Benzofuranyl Esters: Synthesis, Crystal Structure Determination, Antimicrobial and Antioxidant Activities. Molecules 2015, 20, 16566-16581. https://doi.org/10.3390/molecules200916566
Kumar CSC, Then LY, Chia TS, Chandraju S, Win Y-F, Sulaiman SF, Hashim NS, Ooi KL, Quah CK, Fun H-K. Benzofuranyl Esters: Synthesis, Crystal Structure Determination, Antimicrobial and Antioxidant Activities. Molecules. 2015; 20(9):16566-16581. https://doi.org/10.3390/molecules200916566
Chicago/Turabian StyleKumar, C. S. Chidan, Li Yee Then, Tze Shyang Chia, Siddegowda Chandraju, Yip-Foo Win, Shaida Fariza Sulaiman, Nurul Shafiqah Hashim, Kheng Leong Ooi, Ching Kheng Quah, and Hoong-Kun Fun. 2015. "Benzofuranyl Esters: Synthesis, Crystal Structure Determination, Antimicrobial and Antioxidant Activities" Molecules 20, no. 9: 16566-16581. https://doi.org/10.3390/molecules200916566