Abstract
Twenty-seven novel pyrrolidine-2,4-dione derivatives containing N-substituted phenylhydrazine moiety were synthesized. Their structures were confirmed by 1H NMR, 13C NMR and MS. The half effective concentration (EC50) values of the title compounds against the phytopathogenic fungi Rhizoctonia cerealis were evaluated. Compounds 6l and 6q displayed good bioactivity with EC50 values of 1.626 and 2.043 μg/mL, respectively. The 3D quantitative structure activity relationship(3D-QSAR) model of CoMFA was established with reliable cross-validated correlation coefficient q 2 value of 0.585 and Noncross-validated correlation coefficient r 2 value of 0.971. This model provided a tool for guiding further design and synthesis of novel pyrrolidine-2,4-dione derivatives with high fungicidal activity.
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Rosett T., Sankhala R. H., Stickings C. E., Taylor M. E. U., Thomas R., Biochem. J., 1957, 67, 390
Gitterman C. O., J. Med. Chem., 1965, 8, 483
Miller F. A., Rightsel W. A., Sloan B., Ehrlich J., French J. C., Bartz Q. R., Nature, 1963, 200, 1338
Gallardo G. L., Peña N. I., Chacana P., Terzolo H. R., Cabrera G. M., World J. Microb. Biot., 2004, 20, 609
Chen S. G., Xu X. M., Dai X. B., Yang C. L., Qiang S., BBA Biomembranes, 2007, 1767, 306
Wang X. F., Si T. F., Li Q. B., Zhu Z. Y., Zhu X. J., Qiang S., Yang C. L., Arkivoc., 2010, ii, 31
Jeong Y. C., Anwar M., Moloney M. G., Bioorg. Med. Chem. Lett., 2014, 24, 1901
Zhu Y. Q., Si X. K., Zou X. M., Liu B., Yang H. Z., Chin. J. Org. Chem., 2007, 27(3), 385
Lu G. H., Chu H. B., Chen M., Yang C. L., Chin. Chem. Lett., 2014, 25, 61
Ali A., Fisara P., Freemont J. A., Kyi S., Meyer A. G., Riches A. G., Sargent R. M., Sawutz D. G., Turner K, A., Winzenberg K. N., Yang Q., Bioorg. Med. Chem. Lett., 2010, 20, 649
Chen S. J., Sun L. J., Koya K., Tatsuta N., Xia Z. Q., Korbut T., Du Z. J., Wu J., Liang G. Q., Jiang J., Ono M., Zhou D., Sonderfan A., Bioorg. Med. Chem. Lett., 2013, 23, 5070
Liu Q., Zhou Y. H., Xuan B., Chiou G. C. Y., Okawara T., J. Ocul. Pharmacol. Th., 2000, 16(1), 81
Guo D. D., Wang Z. W., Fan Z. J., Zhao H., Zhang W., Cheng J. G., Yang J. Q., Wu Q. J., Zhang Y. J., Fan Q., Chin. J. Chem., 2012, 30, 2522
Rao G. W., Wang C., Wang J., Zhao Z. G., Hu W. X., Bioorg. Med. Chem. Lett., 2013, 23, 6474
Zhang X. Y., Deng D. J., Tan J. J., He Y., Li C. H., Wang C. X., Chem. Res. Chinese Universities, 2014, 30(2), 297
Zhu X. J., Hang L., Wang X. F., Zhu Z. Y., Zheng X. Q., Qiang S., Yang C. L., Chin. J. Org. Chem., 2009, 29(11), 1784
Matsuo K., Kimura M., Kinuta T., Takai N., Tanaka K., Chem. Pharm. Bull., 1984, 32(10), 4197
Lerch U., König J., Synthesis, 1983, 157
Rosamilia A. E., Aricò F., Tundo P., J. Org. Chem., 2008, 73, 1559
Athanasellis G., Gavrielatos E., Igglessi-Markopoulou O., J. Heterocycl. Chem., 2001, 38, 1203
Niu Z. G., Li D. C., Liu D., Xia D., Zou Y., Sun W., Li G. N., Chem. Res. Chinese Universities, 2014, 30(3), 425
Arulmani R., Sankaran K. R., Spectrochim Acta A, 2014, 129, 491
Skylaris C. K., Igglessi-Markopoulou O., Detsi A., Markopoulos J., Chem. Phys., 2003, 293, 355
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Supported by the National High Technology Research and Development Program of China(No.2011AA10A206), the National Key Technologies R&D Program of China(No.2011BAE06B04), the Science & Technology Pillar Program of Jiangsu Province, China(No.BE2012371), the National Natural Science Foundation of China(No.31171889) and the Fundamental Research Funds for the Central Universities of China(No.KYZ201223).
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Zhang, L., Ren, Z., Lu, A. et al. Synthesis, biological activity and 3D-QSAR study of novel pyrrolidine-2,4-dione derivatives containing N-substituted phenylhydrazine moiety. Chem. Res. Chin. Univ. 31, 228–234 (2015). https://doi.org/10.1007/s40242-015-4348-3
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DOI: https://doi.org/10.1007/s40242-015-4348-3