Antibacterial and Antitumor Activities of Biscoumarin and Dihydropyran Derivatives
Abstract
:1. Introduction
2. Results and Discussion
2.1. Molecular Structure
2.2. Hydrogen Bonds Energies in Biscoumarins 1–4
System | Total Electronic Energies a,b | E(O6–H6···O1) | E(O3–H3···O4) | E(Total HB) c |
---|---|---|---|---|
1ab | −1711.038294 | −116.20463 | ||
1a | −1711.018741 | −51.3364015 | ||
1b | −1711.013587 | −64.8682285 | ||
2ab | −2332.538245 | −115.7031595 | ||
2a | −2332.518779 | −51.107983 | ||
2b | −2332.513642 | −64.5951765 | ||
3ab | −2025.68685 | −118.0346035 | ||
3a | −2025.666896 | −52.389227 | ||
3b | −2025.661847 | −65.6453765 | ||
4ab | −1625.791083 | −121.970228 | ||
4a | −1625.770804 | −53.2425145 | ||
4b | −1625.764906 | −68.7277135 |
2.3. Minimal Inhibitory Concentration (MIC) Assay
Drugs | MIC (µg/mL) | |||
---|---|---|---|---|
S. aureas (ATCC 29213) | MRSA (XJ 75302) | Mu50 (ATCC 700699) | LAC (USA 300) | |
Compound 1 | 16 | 16 | 8 | 8 |
Compound 2 | 4 | 4 | 2 | 2 |
Compound 3 | 64 | 64 | 64 | 64 |
Compound 4 | >256 | >256 | >256 | >256 |
Compound 5 | >256 | >256 | >256 | >256 |
Compound 6 | >256 | >256 | >256 | >256 |
Compound 7 | >256 | >256 | >256 | >256 |
Compound 8 | >256 | >256 | >256 | >256 |
Compound 9 | >256 | >256 | >256 | >256 |
Compound 10 | >256 | >256 | >256 | >256 |
Compound 11 | >256 | >256 | >256 | >256 |
Compound 12 | >256 | >256 | >256 | >256 |
Compound 13 | >256 | >256 | >256 | >256 |
Levofloxacin | <0.125 (S) | 4 (R) | 4 (R) | 8 (R) |
Ceftazidime | 8 (S) | >256 (R) | 256 (R) | 64 (R) |
Ceftriaxone | 2 (S) | >256 (R) | 256 (R) | 32 (R) |
Gentamicin | 0.12 (S) | 64 (R) | 32 (R) | 0.25 (S) |
Piperacillin | 2 (S) | >128 (R) | >128 (R) | 8 (R) |
2.4. In Vitro Antitumor Activity
Drugs | HUTU 80 | 4T1 | PANC1 | |||
---|---|---|---|---|---|---|
IC50 | IC90 | IC50 | IC90 | IC50 | IC90 | |
Compound 1 | 32.63 | 64.55 | 22.09 | 39.58 | 27.52 | 51.33 |
Compound 2 | 28.94 | 55.87 | 18.78 | 36.05 | 25.05 | 46.67 |
Compound 3 | 28.42 | 55.31 | 20.08 | 38.21 | 28.01 | 51.75 |
Compound 4 | 28.55 | 55.61 | 19.33 | 36.92 | 26.11 | 48.56 |
Compound 5 | 116.00 | 216.00 | 138.00 | 248.07 | 79.23 | 154.62 |
Compound 6 | 130.67 | 264.00 | 163.67 | 304.96 | 149.42 | 302.09 |
Compound 7 | 209.00 | 409.00 | 91.44 | 186.16 | 174.71 | 339.00 |
Compound 8 | 266.79 | 483.83 | 214.87 | 330.92 | 172.99 | 317.39 |
Compound 9 | 582.88 | 1079.16 | 333.93 | 638.81 | 744.59 | 1340.72 |
Compound 10 | 493.58 | 942.01 | 303.98 | 601.82 | 566.14 | 1055.13 |
Compound 11 | 268.72 | 490.94 | 316.54 | 569.07 | 305.25 | 592.40 |
Compound 12 | 509.78 | 985.97 | 621.34 | 1117.62 | 604.45 | 1143.73 |
Compound 13 | 374.50 | 707.83 | 481.83 | 900.82 | 205.17 | 410.09 |
Carboplatin | 65.62 | 126.24 | 45.85 | 102.13 | 52.94 | 109.94 |
3. Experimental Section
3.1. Apparatus and Materials
3.2. Synthesis and Characterization of Compounds 1–13
3.3. X-ray Crystallography
Compound 3 | Compound 7 | Compound 9 | Compound 11 | |
---|---|---|---|---|
Formula | C26H18O6S | C20H11F3N2O3 | C18H12F6N2O2 | C18H16Cl2N2O2 |
Mr | 458.08 | 384.31 | 402.3 | 362.06 |
Crystal system | Triclinic | Triclinic | Triclinic | Triclinic |
Space group | Pī | Pī | Pī | Pī |
a/Å | 10.947 (3) | 7.9416 (6) | 8.5762 (6) | 8.2045 (5) |
b/Å | 20.402 (7) | 10.9917 (9) | 8.8891 (8) | 14.1658 (8) |
c/Å | 20.694 (7) | 11.4755 (6) | 12.1026 (8) | 23.3891 (15) |
α/° | 109.44 (3) | 112.429 (7) | 109.583 (7) | 94.540 (5) |
β/° | 90.09 (3) | 105.094 (6) | 92.163 (6) | 97.474 (5) |
γ/° | 93.29 (3) | 97.364 (6) | 97.257 (7) | 98.928 (5) |
V/Å3 | 4350 (3) | 864.45 (11) | 859.13 (11) | 2648.9 (3) |
Z | 2 | 2 | 2 | 2 |
Dcalc/g·cm−3 | 1.401 | 1.447 | 1.555 | 1.357 |
μ(Mo Kα)/mm−1 | 0.191 | 0.122 | 0.146 | 0.38 |
θ range/° | 2.43 to 25.00 | 2.74 to 27.68 | 2.43 to 27.35 | 2.76 to 27.51 |
Reflections collected | 18355 | 5790 | 5819 | 18090 |
No. unique data [R(int)] | 13442 [0.0377] | 3045 [0.0233] | 3030 [0.0213] | 9317 [0.0442] |
No. data with I ≥ 2σ(I) | 5431 | 2170 | 2318 | 6552 |
R1 | 0.0783 | 0.0595 | 0.0745 | 0.0824 |
ωR2(all data) | 0.2469 | 0.1774 | 0.2276 | 0.261 |
3.4. Quantum Chemical Calculations
3.5. Minimal Inhibitory Concentration (MIC) Assay
3.6. Cell Viability Assay
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sui, Y.-P.; Huo, H.-R.; Xin, J.-J.; Li, J.; Li, X.-J.; Du, X.-L.; Ma, H.; Zhou, H.-Y.; Zhan, H.-D.; Wang, Z.-J.; et al. Antibacterial and Antitumor Activities of Biscoumarin and Dihydropyran Derivatives. Molecules 2015, 20, 17614-17626. https://doi.org/10.3390/molecules200917614
Sui Y-P, Huo H-R, Xin J-J, Li J, Li X-J, Du X-L, Ma H, Zhou H-Y, Zhan H-D, Wang Z-J, et al. Antibacterial and Antitumor Activities of Biscoumarin and Dihydropyran Derivatives. Molecules. 2015; 20(9):17614-17626. https://doi.org/10.3390/molecules200917614
Chicago/Turabian StyleSui, Yun-Peng, Hai-Ru Huo, Jia-Jia Xin, Jing Li, Xiao-Jun Li, Xin-Liang Du, Hai Ma, Hai-Yu Zhou, Hong-Dan Zhan, Zhu-Ju Wang, and et al. 2015. "Antibacterial and Antitumor Activities of Biscoumarin and Dihydropyran Derivatives" Molecules 20, no. 9: 17614-17626. https://doi.org/10.3390/molecules200917614