Chinese Journal of Organic Chemistry >
Synthesis and Antifungal Activities of 4-Thioquinoline Compounds
Received date: 2018-01-16
Revised date: 2018-04-21
Online published: 2018-05-14
Supported by
Project supported by the National Natural Science Foundation of China (No. 31601670), the Foundation of Department of Education of Sichuan Province (No. 18ZB0079) and the Youth Science Foundation of Chengdu University of Technology (No. 2017QJ02).
Based on the scaffold of 4-substituted quinoline, twenty-four 4-thioquinoline compounds were designed and synthesized by molecular hybridization. Their structures were identified by 1H NMR, 13C NMR and HRMS. Meanwhile, all target compounds were evaluated for antifungal activities. The results indicated that the majority of target compounds displayed some activity against each of the fungi. Among them, 4-(ethylthio)-2-phenylquinoline (4a), 4-(isopropylthio)-2-phenylquinoline (4c) and 4-(allylthio)-2-phenylquinoline (4h) were more potent than others, whose inhibition rates against some fungi were comparable to the positive drug azoxystrobin. The structure-activity relationship (SAR) showed that different substituents on 4-position could significantly affect activities. Generally, the presence of aliphatic group could be more beneficial to antifungal activity than aromatic group, and the activity weakened with an increase of steric hindrance. Moreover, the kinds and positions of substituents on the aromatic ring had little or negative effects on the activity.
Key words： quinoline; thioether; antifungal activity; synthesis
Yang Rui , Ma Yanni , Huang Ting , Xie Wei , Zhang Xia , Huang Guoshuang , Liu Xiaodong . Synthesis and Antifungal Activities of 4-Thioquinoline Compounds[J]. Chinese Journal of Organic Chemistry, 2018 , 38(8) : 2143 -2150 . DOI: 10.6023/cjoc201801024
[1] Fostel, J. M.; Lartey, P. A. Drug Discovery Today 2000, 5, 25.
[2] Jampilek, J.; Dolezal, M.; Kunes, J.; Buchta, V.; Silva, L.; Kralova, K. Med. Chem. 2005, 1, 591.
[3] Chen, Y. L.; Fang, K. C.; Sheu, J. Y.; Hsu, S. L.; Tzeng, C. C. J. Med. Chem. 2001, 44, 2374.
[4] Narender, P.; Srinivas, U.; Ravinder, M.; Rao, B. A.; Ramesh, C.; Harakishore, K.; Gangadasu, B.; Murthy, U. S. N.; Rao, V. J. Bioorg. Med. Chem. 2006, 14, 4600.
[5] Cheng, H.; Wang, W. Q.; Huang, L.; Cui, P.; Wu, Q. Y. Chin. J. Org. Chem. 2016, 36, 1065(in Chinese). (程华, 汪万强, 黄琳, 崔萍, 吴琼友, 有机化学, 2016, 36, 1065.)
[6] Gao, Z. M.; Wang, T. T.; Li, S. Z.; Wan, H. Q.; Wang, G.; Wu, Y. B.; Deng, X. Q.; Song, M. X. Chin. J. Org. Chem. 2016, 36, 2484(in Chinese). (高智敏, 王田田, 李深圳, 万慧琪, 王刚, 吴银彬, 邓先清, 宋明霞, 有机化学, 2016, 36, 2484.)
[7] Valkó, K. J. Chromatogr. A 2004, 1037, 299.
[8] Ingrid, J. C.; Francoise, B. V.; Mustofa, V.; Alexis, S.; Edouard, M.; Michelem, F.; Isabelle, F. Planta Med. 2002, 68, 68.
[9] Urbina, J. M.; Cortés, J. C. G.; Palma, A.; López, S. N.; Zacchino, S. A.; Enrizd, D.; Ribasb, J. C.; Kouznetzova, V. V. Bioorg. Med. Chem. 2000, 8, 691.
[10] Jain, R.; Vaitilingam, B.; Nayyar, A.; Palde, P. B. Bioorg. Med. Chem. Lett. 2003, 13, 1051.
[11] Du, D.; Fang, J. X. Chin. J. Org. Chem. 2007, 27, 1318(in Chinese). (杜鼎, 方建新, 有机化学, 2007, 27, 1318.)
[12] Chen, G. M.; Wu, Z. B.; Hu, D. Y.; Yang, S.; Bao, W. Y. Fine Chem. Intermed. 2011, 41, 1(in Chinese). (陈广明, 吴志兵, 胡德禹, 杨松, 包文艳, 精细化工中间体, 2011, 41, 1.)
[13] Tian, J. F.; Liu, J.; Sun, X. F.; Chai, B. S.; Liu, C. L. Agrochemicals 2011, 50, 552(in Chinese). (田俊锋, 刘军, 孙旭峰, 柴宝山, 刘长令, 农药, 2011, 50, 552.)
[14] Zhao, J.; Yuan, J. Z.; Zhou, H. J.; Gao, Y.; Liu, D. Pharm. Today 2014, 24, 306(in Chinese). (赵杰, 袁敬竹, 周红娟, 高阳, 刘丹, 今日药学, 2014, 24, 306.)
[15] Zhang, C. R.; Wang, L.; Ge, Y. L.; Ju, X. L. Chin. J. Org. Chem. 2007, 27, 1432(in Chinese). (张成仁, 王柳, 葛燕丽, 巨修练, 有机化学, 2007, 27, 1432.)
[16] Shalaby, A. A.; El-Khamry, A. A.; Shiba, S. A. Arch. Pharmacal Res. 2000, 333, 365.
[17] Chen, W.; Chen, Q.; Wu, Q. Y.; Yang, G. F. Chin. J. Org. Chem. 2005, 25, 1477(in Chinese). (陈悟, 陈琼, 吴琼友, 杨光富, 有机化学, 2005, 25, 1477.)
[18] Xue, W.; Song, B. A.; Yang, S.; Hu, D. Y.; Liu, G.; Liu, P. S.; Zhang, P. Q.; Jin, L. H.; Zhang, S. M. Fine Chem. Intermed. 2006, 36, 16(in Chinese). (薛伟, 宋宝安, 杨松, 胡德禹, 刘刚, 刘平生, 张培权, 金林红, 张素梅, 精细化工中间体, 2006, 36, 16.)
[19] Xu, G. F.; Song, B. A.; Bhadury, P. S.; Yang, S.; Zhang, P. Q.; Jin, L. H.; Xue, W.; Hu, D. Y.; Lu, P. Bioorg. Med. Chem. 2007, 15, 3768.
[20] Liu, G.; Liu, C. P.; Ji, C. N.; Sun, L.; Wen, Q. W. Chin. J. Org. Chem. 2008, 28, 525(in Chinese). (刘刚, 刘春萍, 纪春暖, 孙琳, 温全武, 有机化学, 2008, 28, 525.)
[21] Ma, Y.; Liu, F.; Yan, K.; Song, B. A.; Yang, S.; Hu, D. Y.; Jin, L. H.; Xue, W. Chin. J. Org. Chem. 2008, 28, 1268(in Chinese). (马耀, 刘芳, 严凯, 宋宝安, 杨松, 胡德禹, 金林红, 薛伟, 有机化学, 2008, 28, 1268.)
[22] Zhang, Y. M.S. Thesis, Guizhou University, Guiyang, 2010(in Chinese). (张英, 硕士论文, 贵州大学, 贵阳, 2010.)
[23] Jin, Q. D. M.S. Thesis, Shandong Agricultural University, Taian, 2015(in Chinese). (晋清栋, 硕士论文, 山东农业大学, 泰安, 2015.)
[24] Boateng, C. A.; Zhu, X. Y.; Jacob, M. R.; Khan, S. I.; Walker, L. A.; Ablordeppey, S. Y. Eur. J. Med. Chem. 2011, 46, 1789.
[25] Boateng, C. A.; Eyunni, S. V. K.; Zhu, X. Y.; Etukala, J. R.; Bricker, B. A.; Ashfaq, M. K.; Jacob, M. R.; Khan, S. I.; Walker, L. A.; Ablordeppey, S. Y. Bioorg. Med. Chem. 2011, 19, 458.
[26] Bolden, S.; Zhu, X. Y.; Etukala, J. R.; Boateng, C.; Mazu, T.; Flores-Rozas, H.; Jacob, M, R.; Khan, S. I.; Walker, L. A.; Ablordeppey, S. Y. Eur. J. Med. Chem. 2013, 70, 130.
[27] Bolden, S.; Boateng, C. A.; Zhu, X. Y.; Etukala, J. R.; Eyunni, S. K.; Jacob, M. R.; Khan, S. I.; Ablordeppey, S. Y. Bioorg. Med. Chem. 2013, 21, 7194.
[28] Marques, E. F.; Bueno, M. A.; Duarte, P. D.; Silva, L. R.; Martinelli, A. M.; dos Santos, C. Y.; Severino, R. P.; Brömme, D.; Vieira, P. C.; Corrêa, A. G. Eur. J. Med. Chem. 2012, 54, 10.
[29] Jones, C. P.; Anderson, K. W.; Buchwald, S. L. J. Org. Chem. 2007, 72, 7968.
[30] Ding, D. R.; Li, X.; Wang, X.; Du, Y. L.; Shen, J. K. Tetrahedron Lett. 2006, 47, 6997.
[31] Rocha, D. H. A.; Pinto, D. C. G. A.; Silva, A. M. S. Tetrahedron 2015, 71, 7717.
[32] Xu, G. F.; Song, B. A.; Bhadury, P. S.; Yang, S.; Zhang, P. Q.; Jin, L. H.; Xue, W.; Hu, D. Y.; Lu, P. Bioorg. Med. Chem. 2007, 15, 3768.
[33] Yang, R.; Gao, Z. F.; Zhao, J. Y.; Li, W. B.; Zhou, L.; Miao, F. J. Agric. Food Chem. 2015, 63, 1906.
[34] Nahide, P. D.; Solorio-Alvarado, C. R. Tetrahedron Lett. 2017, 58, 279.
[35] John, H.; Wunsche, E. J. Prakt. Chem. (Leipzig) 1928, 119, 49.
[36] Cuny, G. D.; Robin, M.; Ulyanova, N. P.; Patnaik, D.; Pique, V.; Casano, G.; Liu, J. F.; Lin, X.; Xian, J.; Glicksman, M. A.; Stein, R. L.; Higgins, J. M. Bioorg. Med. Chem. Lett. 2010, 20, 3491.
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