Abstract
As a group of diversified frameworks, quinazolin derivatives displayed a broad field of biological functions, especially as anticancer. To investigate the quantitative structure-activity relationship, 3D-QSAR models were generated with 24 quinazolin scaffold molecules. The experimental and predicted pIC50 values for both training and test set compounds showed good correlation, which proved the robustness and reliability of the generated QSAR models. The most effective CoMFA and CoMSIA were obtained with correlation coefficient r2 ncv of 1.00 (both) and leave-one-out coefficient q2 of 0.61 and 0.59, respectively. The predictive abilities of CoMFA and CoMSIA were quite good with the predictive correlation coefficients (r2 pred ) of 0.97 and 0.91. In addition, the statistic results of CoMFA and CoMSIA were used to design new quinazolin molecules.
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References
Alafeefy, A. M., Kadi, A. A., El-Azab, A. S., Abdel-Hamide, S. G., and Daba, M. Y., 2008. Synthesis, analgesic and anti-inflammatory evaluation of some new 3H-quinazolin-4-one derivatives. Archiv Der Pharmazie, 341: 377–385.
Antoszczak, M., Maj, E., Napiórkowska, A., Stefanska, J., Augustynowicz-Kopec, E., Wietrzyk, J., Janczak, J., Brzezinski, B., and Huczynski, A., 2014. Synthesis, anticancer and antibacterial activity of salinomycin N-Benzyl amides. Molecules, 19: 19435–19459.
Hammond, J. R., and Archer, R. G. E., 2003. Interaction of the novel adenosine uptake inhibitor 3-[1-(6,7-Diethoxy-2-morpholinoquinazolin-4-yl)piperidin-4-yl]-1,6-dimethyl-2,4 (1H, 3H)-quinazolinedione Hydrochloride (KF24345) with the es and ei subtypes of equilibrative nucleoside transporters. Journal of Pharmacology and Experimental Therapeutics, 308: 1083–1093.
Joshi, S. D., More, U. A., Aminabhavi, T. M., and Badiger, A. M., 2014. Two-and three-dimensional QSAR studies on a set of antimycobacterial pyrroles: CoMFA, Topomer CoMFA, and HQSAR. Medicinal Chemistry Research, 23: 107–126.
Lokwani, D. K., Mokale, S. N., and Shinde, D. B., 2014. 3D QSAR studies based in silico screening of 4,5,6-triphenyl-1,2,3,4-tetrahydropyrimidine analogs for anti-inflammatory activity. European Journal of Medicinal Chemistry, 73: 233–242.
Wang, X., Xin, M., Xu, J., Kang, B., Li, Y., Lu, S., and Zhang, S., 2015. Synthesis and antitumor activities evaluation of m-(4-morpholinoquinazolin-2-yl)benzamides in vitro and in vivo. European Journal of Medicinal Chemistry, 96: 382–395.
Zhang, H., Hu, J., Zhao, J., and Zhang, Y., 2016. Spectrometric measurements and DFT studies on new complex of copper (II) with 2-((E)-9-ethyl-3-(2-(6-(4-methylpyridin-2-yl)pyridin-3-yl)vinyl)-9H-carbazole. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 168: 78–85.
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The authors would like to acknowledge financial supports from the National Natural Science Foundation of China (Nos. 50673085, 20677053), and the National High-Tech Research and Development Programme of China (No. 2010AA09Z203).
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Zhao, S., Zhang, G., Xia, S. et al. DFT and 3D-QSAR Studies of Anti-Cancer Agents m-(4-Morpholinoquinazolin-2-yl) Benzamide Derivatives for Novel Compounds Design. J. Ocean Univ. China 17, 609–613 (2018). https://doi.org/10.1007/s11802-018-3385-1
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DOI: https://doi.org/10.1007/s11802-018-3385-1