Synthesis and Biological Activity of Novel Phosphoramide with Hydantoin

doi:10.6023/cjoc201305023

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (10): 2186-2195.DOI: 10.6023/cjoc201305023 Previous Articles Next Articles

Articles

新型含咪唑啉2,4-二酮的磷酰胺类化合物的合成和生物活性

王进敏^a, 徐志红^a,b, 韩金涛^a, 董宏波^a, 刘斌^a, 王明安^a

a 中国农业大学应用化学系北京 100193;
b 长江大学农学院荆州 434205

收稿日期:2013-05-14 修回日期:2013-06-11 发布日期:2013-06-21
通讯作者: 王明安 E-mail:wangma@cau.edu.cn
基金资助:
“十二五”科技支撑计划(No. 2011BAE06B03);国家自然科学基金(No. 20772150)和南开大学元素有机化学国家重点实验室开放基金(Nos. 0902, 201003)资助项目

Synthesis and Biological Activity of Novel Phosphoramide with Hydantoin

Wang Jinmin^a, Xu Zhihong^a,b, Han Jintao^a, Dong Hongbo^a, Liu Bin^a, Wang Mingan^a

a Department of Applied Chemistry, China Agricultural University, Beijing 100193;
b College of Agricuture, Yangtze University, Jingzhou 434025

Received:2013-05-14 Revised:2013-06-11 Published:2013-06-21
Supported by:
Project supported by the National Key Technologies R&D Program (No. 2011BAE06B03), the National Natural Science Foundation of China (No. 20772150) and the National Key Laboratory of Elemento-Organic Chemistry in Nankai University (No. 0902, 201003).

Based on the synthesis of phosphates and phosphorylamidates with hydantoin, thirty and eight new O,O-dialkyl-(aryl)-5-[4-aminophenyl(benzyl)]-2,4-imidazolidinedione thiophosphoramide derivatives with hydantoin were synthesized by the reaction of O,O-dialkyl(aryl) thiophosphoryl chloride with 5-(4-aminophenyl)-and 5-(4-aminobenzyl)-2,4-imidazolidine-dione intermediates, and their structures were confirmed by ¹H NMR, ³¹P NMR, IR, elemental analysis and X-ray diffraction. 9b: C₁₄H₂₀N₃O₃PS₂·1/3H₂O, M_r=379.43, triclinic, space group P-1, a=0.82092(5) nm, b=1.79810(14) nm, c=2.0153(2) nm, α=72.289(8)°, β=79.355(7)°, γ=77.288(6)°, V=2.7421(4) nm³, D_c=1.379 g/cm³, Z=6, F(000)=1196, μ(Mo Kα)=0.397 mm^-1, S=1.031, final R=0.0426, wR=0.0797. The preliminary bioassay showed that O,O-dimethyl-5-(4-amino-phenyl)-2,4-imidazolidinedione thiophosphoramide (7a), O-ethyl-O-phenyl-5-(4-aminobenzyl)-2,4-imidazolidine-dione thio-phosphoramide (9n) and O,O-dimethyl-5-(3-aminophenyl)-2-thio-2,4-imidazolidinedione thiophosphoramide (11a)have inhibitory rates 75.4%, 80.5% and 81.7% against Brasica campestris at the concentration of 100 μg/mL, while eleven compounds showed excellent insecticidal activities against Myzus Persicae with the LD₅₀ data in the range of 182.41～368.52 μg/mL, respectively.

Key words: 2,4-imidazolidinedione, thiophosphoramide, adenylosuccinate synthetase, biological activity

Cite this article

Wang Jinmin, Xu Zhihong, Han Jintao, Dong Hongbo, Liu Bin, Wang Mingan. Synthesis and Biological Activity of Novel Phosphoramide with Hydantoin[J]. Chin. J. Org. Chem., 2013, 33(10): 2186-2195.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Fonné-Pfister, R.; Chemla, P.; Ward, E.; Girardet, M.; Kreuz, K. E.; Honzatko, R. B.; Fromm, H. J.; Schar, H. P.; Grutrers, M. G.; Cowan-Jacob, S. W. Proc. Natl. Acad. Sci. U. S. A. 1996, 93, 9431.
[2] Nakajima, N.; Itoi, K.; Takamatsu, Y.; Kinoshita, T.; Okazaki, T.; Kawakubo, K.; Shindo, M.; Honma, T.; Tohjigamori, M.; Haneishi, T. J. Antibiot. 1991, 44, 293.
[3] Heim, D. R.; Cseke, C.; Gerwick, B. C.; Murdoch, M. G.; Green, S. B. Pestic. Biochem. Physiol. 1995, 53, 138.
[4] Siehl, D. L.; Subramanian, M. V.; Walters, E. W.; Lee, S. F.; Anderson, F. J.; Toschi, A. G. Plant Physiol. 1996, 110, 753.
[5] (a) Walters, E. W.; Lee, S.-F.; Niderman, T.; Bernasconi, P.; Subramanian, M. V.; Siehl, D. L. Plant Physiol. 1997, 114, 549.
(b) Cseke, C. T.; Gerwick, B. C.; Crouse, B. C.; Murdoch, M. G.; Green, S. B.; Heim, D. R. Pestic. Biochem. Physiol. 1996, 55, 210.
[6] (a) Poland, B. W.; Silva, M. M.; Serra, M. A.; Cho, Y.; Kim, K. H.; Harris, E. M.; Honzatko, R. B. J. Biol. Chem. 1993, 268, 25334.
(b) Poland, B. W.; Hou, Z. L.; Bruns, C.; Fromm, H. J.; Honzatko, R. B. J. Biol. Chem. 1996, 271, 15407.
[7] (a) Wang, J. M.; Han, J. T.; Kuang, Y.; Jin, S. H.; Wang, M. A. Chin. J. Pestic. Sci. 2008, 10, 392 (in Chinese). (王进敏, 韩金涛, 匡宇, 金淑惠, 王明安, 农药学学报, 2008, 10, 392.)
(b) Wang, J. M.; Kuang, Y.; Han, J. T.; Jin, S. H.; Wang, M. A. Chin. J. Pestic. Sci. 2009, 11, 1 (in Chinese).(王进敏, 匡宇, 韩金涛, 金淑惠, 王明安, 农药学学报, 2009, 11, 1.)
[8] (a) Crouse. G. D.; Johnston, R. D.; Heim, D. R.; Cseke, C. T.; Webster, J. D. Synthesis and Chemistry of Agro-chemicals V, Washington DC, American Chemical Society, 1998, Chapter 13, pp. 120～133.
(b) Hanessian, S.; Lu, P. P.; Sancéau, J. Y.; Chemla, P.; Gohda, K.; Fonne-Pfister, R.; Prade, L.; Cowan-Jacob, S. W. Angew. Chem., Int. Ed. 1999, 38, 3160.
(c) Tibrewal, N.; Elliott, G. I. Bioorg. Med. Chem. Lett., 2011, 21, 517.
(d) Zhang, Y.; Elliott, G. I.; Saldanha, A.; Carson, D. A.; Wrasidlo,
W. Beilstein J. Org. Chem. 2010, 6, 742.
(e) Boitz, J. M.; Strasser, R.; Yates, P. A.; Jardim, A.; Ullman, B. J. Biol. Chem. 2013, 288, 8977.
(f) Wiest, A.; McCarthy, A. J.; Schnittker, R.; McCluskey, K. J. Genet. 2012, 91, 199.
[9] Wang, Y. P.; Wang, M. A.; Du, F. P.; Li, X. D.; Yao, G. W.; Zhang, P. D.; Lu, H. Z. Chem. J. Chin. Univ. 2010, 31, 336 (in Chinese).(汪月鹏, 王明安, 杜凤沛, 李向东, 姚广伟, 张潘丹, 路慧哲, 高等学校化学学报, 2010, 31, 336.)
[10] Xu, Z. H.; Wang, J. M.; Han, J. T.; Liu, B.; Wang, M. A. Chin. J. Org. Chem. 2012, 32, 2134 (in Chinese). (徐志红, 王进敏, 韩金涛, 刘斌, 王明安, 有机化学, 2012, 32, 2134.)
[11] Han, J. T.; Wang, J. M.; Dong H. B.; Xu, Z. H.; Liu, B.; Wang, M. A. Chin. J. Org. Chem. 2013, 33, 596 (in Chinese).(韩金涛, 王进敏, 董宏波, 徐志红, 刘斌, 王明安, 有机化学, 2013, 33, 596.)
[12] Connors, T. A.; Ross, W. C. J.; Wilson, J. G. J. Chem. Soc. 1960, 2994.
[13] Wang, J. M.; Han, J. T.; Zhang, C. Y.; Qiu, L. H.; Wang, M. A. Chin. J. Org. Chem. 2010, 30, 72 (in Chinese).(王进敏, 韩金涛, 张春艳, 邱立红, 王明安, 有机化学, 2010, 30, 72.)
[14] Burckhalter, J. H.; Stephens, V. C. J. Am. Chem. Soc., 1951, 73, 56.
[15] Wang, Z. D.; Sheikh, S. O.; Zhang, Y. Molecules 2006, 11, 739.
[16] Szeszel-Fedorowicz, W.; Lisowski, M.; Rosiñski, G.; Issberner, J.; Osborne, R.; Nopiñska, D. Polish J. Chem. 2001, 75, 411.
[17] Sassatelli, M.; Debiton, é.; Aboab, B.; Prudhomme, M.; Moreau P. Eur. J. Med. Chem. 2006, 41, 709.
[18] Han, J. T.; Wang, J. M.; Chen, S. C.; Qiu, L. H.; Wang, M. A. Chin. J. Org. Chem. 2010, 30, 691 (in Chinese).(韩金涛, 王进敏, 陈守聪, 邱立红, 王明安, 有机化学, 2010, 30, 691.)
[19] Huang, R. Q.; Wang, H. L.; Zhou, J. Preparation of Organic Intermediates, Chemical Industry Press, Beijing, 1997, p. 166 (in Chinese).(黄润秋, 王惠林, 周嘉, 有机中间体制备, 化学工业出版社, 北京, 1997, p. 166.)

新型含咪唑啉2,4-二酮的磷酰胺类化合物的合成和生物活性

Synthesis and Biological Activity of Novel Phosphoramide with Hydantoin

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Mingjia Guang, Shuo Jiang, Baoyu Zhu, Rusong Zhang, Kunpeng Wang, Minghui Wang, Liangzhong Xu. Design, Synthesis and Insecticidal, Acaricidal Activities of Novel Pyrrole-2-carboxylic Acid and Their Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2895-2904.
[2]	Qifan Wang, Yuanquan Zhang, Li Xing, Yuanxiang Zhou, Chenyu Gong, Bangcan He, Nian Zhang, Yongjun Wu, Wei Xue. Design, Synthesis and Biological Activity of Myricetin Derivatives Containing 1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazole [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1525-1536.
[3]	Can Yong, Yun Li, Tao Bi, Guofeng Chen, Dongxia Zheng, Zhouyu Wang, Yuanyuan Zhang. Research Progress on the Synthesis and Activity of D-Galactose Derived Small Galectin Inhibitors [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1307-1325.
[4]	Jie Luo, Yaqian Yan, Haoxin Wang, Yaoyao Li. Discovery of a New Polycyclic Tetramate Macrolactam Clifednamide K [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1224-1228.
[5]	Yajun Mao, Xiangmin Shao, Yangjie Li, Ruimei Cao, Yali Feng, Guangyu Zhai. Research Progress on the Synthesis of Quercetin Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3588-3605.
[6]	Hongliang Xu, Jing Su, Zishi Wang, Chenxin Hou, Pengchong Wu, Yue Xing, Xiangshuai Li, Xiaolei Zhu, Yuncai Lu, Lijian Xu. Synthesis, Design and Three-Dimensional Quantitative Structure Activity Relationship (3D-QSAR) Research of Phenylpyrrole Fungicides [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3560-3570.
[7]	Xiaotian Qin, Junchao Zhang, Yuqing He, Rui Zhang, Hua Cheng, Cheng Chen, Xin Qin. Synthesis and Biological Activities of Coenzyme Q Derivatives Containing (4-Aryloxylaryl)amino Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2045-2054.
[8]	Meng Xu, Shenyuan Gao, Yuanxu Zeng, Anhui Gao, Lixin Gao, Lei Xu, Yubo Zhou, Jianrong Gao, Qing Ye, Jia Li. Synthesis and Evaluation of 3-(Indol-3-yl)-4-(pyrazolo[3,4- c]pyridazin-3-yl)maleimides as Potent Mutant Isocitrate Dehydrogenase-1 Inhibitors [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1991-2000.
[9]	Ting Jiang, Hong Pu, Yanwen Duan, Xiaohui Yan, Yong Huang. New Natural Products of Streptomyces Sourced from Deep-Sea, Desert, Volcanic, and Polar Regions from 2009 to 2020 [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1804-1820.
[10]	Jun He, Xuemei Tang, Qing Zhou, Feng Peng, Tingting Liu, Liwei Liu, Ming He, Chengwei Xie, Wei Xue. Design, Synthesis and Biological Activities of Myricetin Derivatives Containing Quinazoline Thioether Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 708-718.
[11]	Zhenguo Zhang, Xiaoxiao Liu, Xinlong Zong, Yalin Yuan, Shuanglei Liu, Ting Zhang, Zishang Wu, Jingying Yang, Zhenhua Jia. Recent Advance on the Synthesis of 3,3'-Bisindolylmethane Derivatives under Transition-Metal-Free Catalytic Conditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 52-64.
[12]	Liang Wei, Tan Chengxia, Weng Jianquan, Liu Xinghai. Advances on Synthesis and Biological Activities of Mesoionic Compounds [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2702-2713.
[13]	Li Qianqian, Wu Zhongmei, Zhang Min, Zhang Yiping, Zhou Yingkai, Deng Hongmei, Song Liping. Synthesis and Preliminary Exploration of Biological Activity of 3-Aryl-4-arylamine Methyl Isoxazoles [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2108-2113.
[14]	Yu Youpei, Duan Wengui, Lin Guishan, Kang Guoqiang, Wang Xiaoyu, Lei Fuhou. Synthesis, Biological Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of Novel 4-Methyl-1,2,4-triazole-thioethers Containing gem-Dimethylcyclopropane Ring [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1647-1657.
[15]	Zhang Junhui, Zhu Yabo, Weng Jianquan, Yu Qian, Yuan Jing, Chen Jie. Synthesis and Biological Activity of Natural Stilbene-Inspired Substituted Styrylthiazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 1055-1061.