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Synthesis and biological activities of novel 2-amino-1,3-thiazole-4-carboxylic acid derivatives

Feng-Yun Li ,  Xiao-Feng Guo ,  Zhi-Jin Fan ,  Yu-Qing Zhang ,  Guang-Ning Zong ,  Xiao-Lin Qian ,  Liu-Yong Ma ,  Lai Chen ,  Yu-Jie Zhu ,  Kalinina Tatiana ,  Yury Yu. Morzherin ,  Nataliya P. Belskaya

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Citation:  Feng-Yun Li, Xiao-Feng Guo, Zhi-Jin Fan, Yu-Qing Zhang, Guang-Ning Zong, Xiao-Lin Qian, Liu-Yong Ma, Lai Chen, Yu-Jie Zhu, Kalinina Tatiana, Yury Yu. Morzherin, Nataliya P. Belskaya. Synthesis and biological activities of novel 2-amino-1,3-thiazole-4-carboxylic acid derivatives[J]. Chinese Chemical Letters, 2015, 26(10): 1315-1318. doi: 10.1016/j.cclet.2015.05.040 shu

Synthesis and biological activities of novel 2-amino-1,3-thiazole-4-carboxylic acid derivatives

    • 通讯作者: Zhi-Jin Fan,
    Nataliya P. Belskaya,
  • 基金项目:

    This work was partially supported by The International Science & Technology Cooperation Program of China (No. 2014DFR41030). Nataliya P. Belskaya thanks Russian State Task of Ministry Education  (No. 2014DFR41030)

    Science (No. 4.560.2014/K). Kalinina Tatiana thanks RFBF (No. 13-03-00137). (No. 4.560.2014/K)

摘要: A series of novel 2-amino-1, 3-thiazole-4-carboxylic acid derivatives were designed and synthesized. Their structures were confirmed by melting points, IR, 1H NMR, 13C NMR, and HRMS or elemental analysis. Biological activities of all title compounds including fungicidal activity and antivirus activity were evaluated systematically. Preliminary bioassays indicated that these compounds exhibited good fungicidal activity at 50 μg/mL, compounds 4b and 4i exhibited over 50% activity against six fungi tested. Most compounds showed good activity against TMV with different models in vivo at 100 μg/mL. Compounds 4c and 4e stood out with high effects against TMV in vivo in all models tested, including protective, inactivative, curative, and inductive activities. These data demonstrate a new strategy for fungi and virus control.

English

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    1. [1] Z.J. Fan, X.F. Liu, F.L. Liu, L.L. Bao, Y.G. Zhang, Progress of researches on induced resistance of plant activator, Acta Phytophy. Sin. 32(2005) 87-92.[1] Z.J. Fan, X.F. Liu, F.L. Liu, L.L. Bao, Y.G. Zhang, Progress of researches on induced resistance of plant activator, Acta Phytophy. Sin. 32(2005) 87-92.

    2. [2] Z.J. Fan, Z.G. Shi, H.K. Zhang, et al., Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance, J. Agric. Food Chem. 57(2009) 4279-4286.[2] Z.J. Fan, Z.G. Shi, H.K. Zhang, et al., Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance, J. Agric. Food Chem. 57(2009) 4279-4286.

    3. [3] C.L. Liu, L. Li, Z.M. Li, Design, synthesis, and biological activity of novel 4-(3, 4-dimethoxyphenyl)-2-methylthiazole-5-carboxylic acid derivatives, Bioorg. Med. Chem. 12(2004) 2825-2830.[3] C.L. Liu, L. Li, Z.M. Li, Design, synthesis, and biological activity of novel 4-(3, 4-dimethoxyphenyl)-2-methylthiazole-5-carboxylic acid derivatives, Bioorg. Med. Chem. 12(2004) 2825-2830.

    4. [4] A.R. Jalilian, S. Sattari, M. Bineshmarvasti, A. Shafiee, M. Daneshtalab, Synthesis and in vitro antifungal and cytotoxicity evaluation of thiazolo-4H-1,2,4-triazoles and 1,2,3-thiadiazolo-4H-1,2,4-triazoles, Arch. Pharm. Med. Chem. 333(2000) 347-354.[4] A.R. Jalilian, S. Sattari, M. Bineshmarvasti, A. Shafiee, M. Daneshtalab, Synthesis and in vitro antifungal and cytotoxicity evaluation of thiazolo-4H-1,2,4-triazoles and 1,2,3-thiadiazolo-4H-1,2,4-triazoles, Arch. Pharm. Med. Chem. 333(2000) 347-354.

    5. [5] S. Vengurlekar, S. Prachand, S. Jain, R. Gupta, Synthesis and evaluation of some thiazole derivatives as an antifungal agent, Int. J. Pharm. Life Sci. 5(2014) 3526-3530.[5] S. Vengurlekar, S. Prachand, S. Jain, R. Gupta, Synthesis and evaluation of some thiazole derivatives as an antifungal agent, Int. J. Pharm. Life Sci. 5(2014) 3526-3530.

    6. [6] T.T. Wang, G.F. Bing, X. Zhang, et al., Synthesis and herbicidal activities of 2-cyano-3-benzylaminoacrylates containing thiazole moiety, Bioorg. Med. Chem. Lett. 20(2010) 3348-3351.[6] T.T. Wang, G.F. Bing, X. Zhang, et al., Synthesis and herbicidal activities of 2-cyano-3-benzylaminoacrylates containing thiazole moiety, Bioorg. Med. Chem. Lett. 20(2010) 3348-3351.

    7. [7] H. Dai, Y.S. Xiao, Z. Li, X.Y. Xu, X.H. Qian, The thiazoylmethoxy modification on pyrazole oximes:synthesis and insecticidal biological evaluation beyond acaricidal activity, Chin. Chem. Lett. 25(2014) 1014-1016.[7] H. Dai, Y.S. Xiao, Z. Li, X.Y. Xu, X.H. Qian, The thiazoylmethoxy modification on pyrazole oximes:synthesis and insecticidal biological evaluation beyond acaricidal activity, Chin. Chem. Lett. 25(2014) 1014-1016.

    8. [8] X. Qin, H.B. Yu, H. Dai, et al., Synthesis and plant-growth regulatory activities of novel imine derivatives containing 1H-1,2,4-triazole and thiazole rings, Chin. Chem. Lett. 21(2010) 283-286.[8] X. Qin, H.B. Yu, H. Dai, et al., Synthesis and plant-growth regulatory activities of novel imine derivatives containing 1H-1,2,4-triazole and thiazole rings, Chin. Chem. Lett. 21(2010) 283-286.

    9. [9] H.B. Yu, L. Shao, J.X. Fang, Synthesis and biological activity research of novel ferrocenyl-containing thiazole imine derivatives, J. Organomet. Chem. 692(2007) 991-996.[9] H.B. Yu, L. Shao, J.X. Fang, Synthesis and biological activity research of novel ferrocenyl-containing thiazole imine derivatives, J. Organomet. Chem. 692(2007) 991-996.

    10. [10] A.S. Mayhoub, M. Khaliq, C. Botting, et al., An investigation of phenylthiazole antiflaviviral agents, Bioorg. Med. Chem. 19(2011) 3845-3854.[10] A.S. Mayhoub, M. Khaliq, C. Botting, et al., An investigation of phenylthiazole antiflaviviral agents, Bioorg. Med. Chem. 19(2011) 3845-3854.

    11. [11] P. Maienfisch, M. Angst, F. Brandl, et al., Chemistry and biology of thiamethoxam:a second generation neonicotinoid, Pest Manag. Sci. 57(2001) 906-913.[11] P. Maienfisch, M. Angst, F. Brandl, et al., Chemistry and biology of thiamethoxam:a second generation neonicotinoid, Pest Manag. Sci. 57(2001) 906-913.

    12. [12] M.H. Lee, S.M. Pan, T.W. Ng, et al., Mutations of β-tubulin codon 198 or 200 indicate thiabendazole resistance among isolates of Penicillium digitatum collected from citrus in Taiwan, Int. J. Food Microbiol. 150(2011) 157-163.[12] M.H. Lee, S.M. Pan, T.W. Ng, et al., Mutations of β-tubulin codon 198 or 200 indicate thiabendazole resistance among isolates of Penicillium digitatum collected from citrus in Taiwan, Int. J. Food Microbiol. 150(2011) 157-163.

    13. [13] H.C. Feng, Novel fungicide benthiavalicarbisopropyl, World Pestic. 30(2008) 51.[13] H.C. Feng, Novel fungicide benthiavalicarbisopropyl, World Pestic. 30(2008) 51.

    14. [14] J. Huang, D. Wu, H.J. Ge, S.H. Liu, J. Yin, Fluorinated 1,8-naphthalimides:synthesis, solid structure and properties, Chin. Chem. Lett. 25(2014) 1399-1402.[14] J. Huang, D. Wu, H.J. Ge, S.H. Liu, J. Yin, Fluorinated 1,8-naphthalimides:synthesis, solid structure and properties, Chin. Chem. Lett. 25(2014) 1399-1402.

    15. [15] C.L. Liu, Z.M. Li, B. Zhang, synthesis and biological activity of novel 2-methyl-4-trifluoromethyl-thiazole-5-carboxamide derivatives, J. Fluorine Chem. 125(2004) 1287-1290.[15] C.L. Liu, Z.M. Li, B. Zhang, synthesis and biological activity of novel 2-methyl-4-trifluoromethyl-thiazole-5-carboxamide derivatives, J. Fluorine Chem. 125(2004) 1287-1290.

    16. [16] Y.B. Chen, J.L. Li, X.S. Shao, X.Y. Xu, Z. Li, Design, synthesis and insecticidal activity of novel anthranilic diamides with benzyl sulfide scaffold, Chin. Chem. Lett. 24(2013) 673-676.[16] Y.B. Chen, J.L. Li, X.S. Shao, X.Y. Xu, Z. Li, Design, synthesis and insecticidal activity of novel anthranilic diamides with benzyl sulfide scaffold, Chin. Chem. Lett. 24(2013) 673-676.

    17. [17] Z.Y. Yu, G.Y. Shi, Q. Sun, et al., Design, synthesis and in vitro antibacterial/antifungal evaluation of novel 1-ethyl-6-fluoro-1, 4-dihydro-4-oxo-7(1-piperazinyl) quinoline-3-carboxylic acid derivatives, Eur. J. Med. Chem. 44(2009) 4726-4733.[17] Z.Y. Yu, G.Y. Shi, Q. Sun, et al., Design, synthesis and in vitro antibacterial/antifungal evaluation of novel 1-ethyl-6-fluoro-1, 4-dihydro-4-oxo-7(1-piperazinyl) quinoline-3-carboxylic acid derivatives, Eur. J. Med. Chem. 44(2009) 4726-4733.

    18. [18] C.B. Vicentini, C. Romagnoli, E. Andreotti, D. Mares, Synthetic pyrazole derivatives as growth inhibitors of some phytopathogenic fungi, J. Agric. Food Chem. 55(2007) 10331-10338.[18] C.B. Vicentini, C. Romagnoli, E. Andreotti, D. Mares, Synthetic pyrazole derivatives as growth inhibitors of some phytopathogenic fungi, J. Agric. Food Chem. 55(2007) 10331-10338.

    19. [19] H. Cerecetto, E. Dias, R.D. Maio, et al., Synthesis and herbicidal activity of N-oxide derivatives, J. Agric. Food Chem. 48(2000) 2995-3002.[19] H. Cerecetto, E. Dias, R.D. Maio, et al., Synthesis and herbicidal activity of N-oxide derivatives, J. Agric. Food Chem. 48(2000) 2995-3002.

    20. [20] V. Ehmke, J.E.Q. Quinsaat, P. Rivera-Fuentes, et al., Tuning and predicting biological affinity:aryl nitriles as cysteine protease inhibitors, Org. Biomol. Chem. 10(2012) 5764-5768.[20] V. Ehmke, J.E.Q. Quinsaat, P. Rivera-Fuentes, et al., Tuning and predicting biological affinity:aryl nitriles as cysteine protease inhibitors, Org. Biomol. Chem. 10(2012) 5764-5768.

    21. [21] N.P. Belskaya, K.I. Lugovik, A.D. Ivina, V.A. Bakulev, Z.J. Fan, Reaction of enamines and azaenamines containing a thioamide group with dimethyl acetylenedicarboxylate, Chem. Heterocycl. Compd. 50(2014) 888-900.[21] N.P. Belskaya, K.I. Lugovik, A.D. Ivina, V.A. Bakulev, Z.J. Fan, Reaction of enamines and azaenamines containing a thioamide group with dimethyl acetylenedicarboxylate, Chem. Heterocycl. Compd. 50(2014) 888-900.

    22. [22] Z.J. Fan, Z.K. Yang, H.K. Zhang, et al., Synthesis, crystal structure, and biological activity of 4-methyl-1,2,3-thiadiazole-containing 1,2,4-triazolo[3,4-b] [1,3,4] thiadiazoles, J. Agric. Food. Chem. 58(2010) 2630-2636.[22] Z.J. Fan, Z.K. Yang, H.K. Zhang, et al., Synthesis, crystal structure, and biological activity of 4-methyl-1,2,3-thiadiazole-containing 1,2,4-triazolo[3,4-b] [1,3,4] thiadiazoles, J. Agric. Food. Chem. 58(2010) 2630-2636.

    23. [23] Y.D. Li, W.T. Mao, Z.J. Fan, et al., Synthesis and biological evaluation of novel 1,2, 4-triazole containing 1,2,3-thiadiazole derivatives, Chin. Chem. Lett. 24(2013) 1134-1136.[23] Y.D. Li, W.T. Mao, Z.J. Fan, et al., Synthesis and biological evaluation of novel 1,2, 4-triazole containing 1,2,3-thiadiazole derivatives, Chin. Chem. Lett. 24(2013) 1134-1136.

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  • 发布日期:  2015-06-01
  • 收稿日期:  2015-01-22
  • 网络出版日期:  2015-04-27
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