Design, Synthesis and Bioactivity of Novel 2-Aryl-4-alkylthiazole-5-carboxylic Acid Derivatives

doi:10.6023/cjoc201207004

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2115-2121.DOI: 10.6023/cjoc201207004 Previous Articles Next Articles

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新型2-芳基-4-烷基噻唑甲酸衍生物的设计、合成与生物活性研究

朱有全, 王丹阳, 袁燕伟, 马源, 邹小毛, 杨华铮

南开大学元素有机化学研究所元素有机化学国家重点实验室天津 300071

收稿日期:2012-07-04 修回日期:2012-07-16 发布日期:2012-07-19
通讯作者: 朱有全, 邹小毛 E-mail:zyq8165@nankai.edu.cn
基金资助:
国家自然科学基金(Nos. 20772066, 21072108)、国家973计划(No. 2010CB126103)和“十二五”科技支撑计划(No. 2011BAE06B05-3)资助项目.

Design, Synthesis and Bioactivity of Novel 2-Aryl-4-alkylthiazole-5-carboxylic Acid Derivatives

Zhu Youquan, Wang Danyang, Yuan Yanwei, Ma Yuan, Zou Xiaomao, Yang Huazheng

State Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Received:2012-07-04 Revised:2012-07-16 Published:2012-07-19
Supported by:
Project support by the National Natural Science Foundation of China (Nos. 20772066, 21072108), the National Basic Research Program of China (973 Program) (No. 2010CB126103) and the National Key Technologies R&D Program (No. 2011BAE06B05-3).

To find new lead compounds with muti-bioactivities, a series of novel 1,3-thiazole-5-carboxylic acid derivatives containing aryloxyacetate were designed via the method of linking active sub-structures, in which the aryloxyacetate with multi-bioactivity was combined to the 1,3-thiazole moiety of ethaboxam, metsulfovax and thifluzamide. The target compounds were synthesized from β-keto acid ester and 4-hydroxybenzothioamide in 6 steps. Their structures were confirmed by ¹H NMR, IR and HRMS techniques. The preliminary bioassay results indicated that some compounds showed obvious inhibition effects against Fusarium graminearum, and the fungicidal activity of 1j is 52% at 50 μg/mL.

Key words: 1,3-thiazole, active sub-structure, phenoxyacetate, thifluzamide, fungicidal activity, herbicidal activity

Cite this article

Zhu Youquan, Wang Danyang, Yuan Yanwei, Ma Yuan, Zou Xiaomao, Yang Huazheng. Design, Synthesis and Bioactivity of Novel 2-Aryl-4-alkylthiazole-5-carboxylic Acid Derivatives[J]. Chin. J. Org. Chem., 2012, 32(11): 2115-2121.

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[1] Zhong, B.; Liu, C.-L.; Li, Z.-M. New Pestic. 2004, 2, 7 (in Chinese).
(钟滨, 刘长令, 李正名, 新农药, 2004, 2, 7.)

[2] Yan, F.-Y.; Liu, D.-Q.; Guan, A.-Y.; Liu, C.-L. Agrochemicals 2003, 42, 46 (in Chinese).
(颜范勇, 刘冬青, 关爱莹, 刘长令, 农药, 2003, 42, 46.)

[3] Liu, C.-L. The Collection of New Pesticide Research, Chemical Industry Press, Beijing, 2002, p. 132 (in Chinese).
(刘长令, 新农药研究开发文集, 化学工业出版社, 北京, 2002, p. 132.)

[4] Bartroli, J.; Turmo, E.; Alguero, M.; Boncompte, E.; Vericat, M. L.; Conte, L.; Ramis, J.; Merlos, M.; Garcia-Rafanell, J.; Forn, J. J. Med. Chem. 1998, 41, 1855.

[5] Shuji, M.; Hiroyuki, K.; Takami, Y.; Menetsugu, M.; Junji, K.; Noriaki, K.; Mitsuru, I. JP 10067759, 1998 [Chem. Abstr. 1998, 128, 217365].

[6] Tang, C.-C.; Li, Y.-C.; Chen, B.; Yang, H.-Z.; Jin, G.-Y. Pesticide Chemistry, Nankai University Press, Tianjin, 1998, pp. 488～454 (in Chinese).
(唐除痴, 李煜昶, 陈彬, 杨华铮, 金桂玉, 农药化学, 南开大学出版社, 天津, 1998, pp. 488～454.)

[7] Liu, C.-L. World Pesticides, Chemical Industry Press, Beijing, 2002, pp. 200～202 (in Chinese).
(刘长令, 世界农药, 化学工业出版社, 北京, 2002, pp. 200～202.)

[8] Dmitri, V. S.; Mikhail, V.; Vyacheslav, Y. S.; Helma, W.; Olesya, K.; Vera, V.; Nikolay, E. S.; Valentine, G. N.; Enno, L.; Gerd- Volker, R. Tetrahedron 2009, 65, 7538.

[9] Robbins, T. A.; Zhu, H.; Shao, J. US 20050027128, 2005 [Chem. Abstr. 2005, 142, 176830].

[10] Varma, R. S.; Chauhan, S.; Prasad, C. R. Indian J. Chem., Sect. B 1988, 27B, 438.

[11] Michael, L. S.; Véronique, B.; Anne-Bénédict, B.; Thierry, B.; Andrew, G. B.; Frédéric, D.; Marie-Claire, F.; Marie-Hélène, F.; Francoise, J. G.; Didier, A. G.; Millard, H. L.; Alain, L.; Christelle Le G.; Jean, M. L.; Valerie, G. M.; Van-Loc, N.; Edwige, N.; Vipul, P.; Annie, P.; Olivier, P.; Danig, P.; Florent, P.; Géraldine, P.; Cécile, B. R.; Michael, S.; Jérôme, T.; Xu, E. H.; Xu, R. X.; Pascal, M. P. J. Med. Chem. 2007, 50, 685.

[12] 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.)

[13] 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.)

[14] 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.)

[15] Zhu, Y.-Q.; Cheng, J.; Zou, X.-M.; Hu, F.-Z.; Xiao, Y.-H.; Yang, H.-Z. Chin. J. Org. Chem. 2008, 28, 1044 (in Chinese).
(朱有全, 程佳, 邹小毛, 胡方中, 肖玉虹, 杨华铮, 有机化学, 2008, 28, 1044.)

新型2-芳基-4-烷基噻唑甲酸衍生物的设计、合成与生物活性研究

Design, Synthesis and Bioactivity of Novel 2-Aryl-4-alkylthiazole-5-carboxylic Acid Derivatives

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