Chinese Journal of Organic Chemistry >
Design, Synthesis and Bioactivity of Novel 2-Aroyl-5-alkylcyclopentanone Derivatives
Received date: 2012-08-28
Revised date: 2012-09-22
Online published: 2012-09-26
Supported by
Project support by the National Basic Research Program of China (973 Program) (No. 2010CB126103), the National Natural Science Foundation of China (Nos. 20772066, 21072108) and the National Key Technologies R&D Program (No. 2011BAE06B05-3).
To find new lead compounds with muti-bioactivities, a series of novel 2-aroyl-5-alkylcyclopentanone derivatives containing 2-bezoylenthenol were designed on the base of various commercial products. The target compounds were synthesized from diethyl adipate in 6 steps. Their structures were confirmed by IR, 1H NMR spectra, X-ray and elemental analysis or HRMS. The preliminary bioassay results indicated that some compounds showed obvious inhibition effects against Brassica campestris, and the herbicidal activities were more than 60% at 100 μg/mL.
Xu Haizhen , Zhu Youquan , Xie Lifen , Wang Xiaofang . Design, Synthesis and Bioactivity of Novel 2-Aroyl-5-alkylcyclopentanone Derivatives[J]. Chinese Journal of Organic Chemistry, 2013 , 33(01) : 143 -147 . DOI: 10.6023/cjoc201208029
[1] Wu, Y. C.; Hu, F. Z.; Yang, H. Z. Chin. J. Pestic. Sci. 2001, 3, 1 (in Chinese). (吴彦超, 胡方中, 杨华铮, 农药学学报, 2001, 3, 1.)
[2] Zhu, Y. Q.; Hu, F. Z.; Yang, H. Z.; Xu, H. Z. Chemistry 2004, 67, w018 (in Chinese). (朱有全, 胡方中, 杨华铮, 徐海珍, 化学通报, 2004, 67, w018.)
[3] Lee, D. L.; Prisbylla, M. P.; Cromartie, T. H.; Dagarin, D. P.; Howard, S. W.; Provan, W. M.; Ellis, M. K.; Fraser, T.; Mutter, L. C. Weed Sci. 1997, 45, 601.
[4] Wu, C.-S.; Huang, J.-L.; Sun Y.-S.; Yang, D.-Y. J. Med. Chem. 2002, 45, 2222.
[5] Zhu, Y. Q.; Si, X. K.; Zou, X. M.; Liu, B.; Yang, H. Z. Chin. J. Org. Chem. 2007, 27, 385 (in Chinese). (朱有全, 司学凯, 邹小毛, 刘斌, 杨华铮, 有机化学, 2007, 27, 385.)
[6] Zhu, Y. Q.; Zou, X. M.; Hu, F. Z.; Yao, C. S.; Liu, B.; Yang, H. Z. J. Agric. Food Chem. 2005, 53, 9566.
[7] Zhu, Y. Q.; Liu, P.; Si, X. K.; Zou, X. M.; Liu, B.; Song, H. B.; Yang, H. Z. J. Agric. Food Chem. 2006, 54, 7200.
[8] Zhu, Y. Q.; Yao, C. S.; Zou, X. M.; Hu, F. Z.; Liu, B.; Yang, H. Z. Molecules 2005, 10, 427.
[9] Zhu, Y. Q.; Hu, F. Z.; Zou, X. M.; Yao, C. S.; Liu, B.; Li, Y. H.; Yang, H. Z. Chin. J. Org. Chem. 2005, 25, 419 (in Chinese). (朱有全, 胡方中, 邹小毛, 姚昌盛, 刘斌, 李永红, 杨华铮, 有机化学, 2005, 25, 419.)
[10] Stork, G.; Brizzolara, A.; Landesman, H. J. Am. Chem. Soc. 1963, 85, 207.
[11] Magnus, P.; Shen, L. Tetrahedron 1999, 55, 3553.
[12] Francis, H.; Case, E.; Emmbt, R. J. Am. Chem. Soc. 1928, 50, 3062.
[13] Campbell, R. D.; Jung, J. A. J. Org. Chem. 1965, 30, 3711.
[14] Brown, H. C.; Brewster, J. H.; Shechter, H. J. Am. Chem. Soc. 1954, 76, 467.
[15] The crystal structure has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number: CCDC 874907.
[16] Zhu, Y.-Q.; Liu, C.; Zhu, R.; Zhang, J.; Yuan, Y.-W.; Zou, X.-M.; Hu, F.-Z.; Yang, H.-Z. Chin. J. Org. Chem. 2010, 30, 1088 (in Chinese). (朱有全, 刘翠, 朱然, 张金, 袁燕伟, 邹小毛, 胡方中, 杨华铮, 有机化学, 2010, 30, 1088.)
[17] Zhu, Y.-Q.; Zhu, R.; Yuan, Y.-W.; Zhang, J.; Zou, X.-M.; Hu, F.-Z.; Yang, H.-Z. Chin. J. Org. Chem. 2010, 30, 1207 (in Chinese). (朱有全, 朱然, 袁燕伟, 张金, 邹小毛, 胡方中, 杨华铮, 有机化学, 2010, 30, 1207.)
[18] Zhu, Y.-Q.; Liu, W.-M.; Liu, B.; Hu, F.-Z.; Zhu, R.; Zou, X.-M.; Yang, H.-Z. Chin. J. Org. Chem. 2009, 29, 638 (in Chinese). (朱有全, 刘卫敏, 刘斌, 胡方中, 朱然, 邹小毛, 杨华铮, 有机化学, 2009, 29, 638.)
[19] Zhu, Y.-Q.; Wang, D.-Y.; Yuan, Y.-W.; Ma, Y.; Zou, X.-M.; Yang, H.-Z. Chin. J. Org. Chem. 2012, 32, 2115 (in Chinese). (朱有全, 王丹阳, 袁燕伟, 马源, 邹小毛, 杨华铮, 有机化学, 2012, 32, 2115.)
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