Chinese Journal of Organic Chemistry >
Synthesis and Antimicrobial Activities of Novel 1,3,4-Oxa(Thia)- diazole Derivatives Containing 6-Fluoroquinazoline Moiety
Received date: 2020-07-29
Revised date: 2020-08-11
Online published: 2020-09-16
Supported by
the Natural Science Foundation of Guizhou Province(20201Z025); the Young Top-Notch Talent Support Program of Guizhou Provincial Education Department(2018038); the Guizhou Provincial High-Level Overseas Talents Innovation and Entrepreneurship Program(201809)
To search efficient agricultural antimicrobial lead compounds, fifty 1,3,4-oxa(thia)diazole derivatives 6a~6y and 8a~8y containing 6-fluoroquinazoline moiety were designed, synthesized and evaluated for their antimicrobial activities, based on the method of the splicing of bioactive substructures. The structures of target compounds were fully characterized by 1H NMR, 13C NMR, and HRMS spectra, and two compounds 6i and 8x were further confirmed via single crystal X-ray diffraction analysis. The preliminary bioassays revealed that some compounds exhibited good antifungal activity in vitro. For example, compounds 6b, 6d, 6t, 6v and 6x were found to have the inhibition rates of 58%, 58%, 55%, 63% and 60% against Gibberella zeae at 50 μg/mL, respectively. Additionally, compounds 6v and 8v displayed the inhibition efficacies of 71% and 64% against Cytospora mandshurica at 50 μg/mL, respectively. Moreover, compound 6v demonstrated an inhibition rate of 72% against Colletotrichum gloeosporioides at 50 μg/mL. The above activities were all better than that of control agent Hymexazol (51%, 61%, and 70%, respectively). Finally, some compounds also showed certain inhibition potencies in vitro against tested bacteria at 100 μg/mL.
Jun Shi , Na Luo , Muhan Ding , Chuanhui Li , Suran Wan , Peijia Li , Junhong Li , Xiaoping Bao . Synthesis and Antimicrobial Activities of Novel 1,3,4-Oxa(Thia)- diazole Derivatives Containing 6-Fluoroquinazoline Moiety[J]. Chinese Journal of Organic Chemistry, 2021 , 41(2) : 738 -756 . DOI: 10.6023/cjoc202007068
| [1] | Li D.; Zhang S.; Song Z.; Wang G.; Li S. Eur. J. Med. Chem. 2017, 136, 114. |
| [2] | Wang L.; Li C.; Zhang Y.; Qiao C.; Ye Y. J. Agric. Food Chem. 2013, 61, 8632. |
| [3] | Price C.L.; Parker J.E.; Warrilow A. G. S.; Kelly D.E.; Kelly S.L. Pest Manage. Sci. 2015, 71, 1054. |
| [4] | Mansfield J.; Genin S.; Magori S.; Citovsky V.; Sriariyanum M.; Ronald P.; Dow M.; Verdier V.; Beer S.V.; Machado M.A.; Toth I.; Salmond G.; Foster G.D. Mol. Plant Pathol. 2012, 13, 614. |
| [5] | Yang L.; Bao X.P. RSC Adv. 2017, 7, 34005. |
| [6] | Zhang M.; Dai Z.C.; Qian S.S.; Liu J.Y.; Xiao Y.; Lu A.M.; Zhu H.L.; Wang J.X.; Ye Y.H. J. Agric. Food Chem. 2014, 62, 9637. |
| [7] | Khan I.; Ibrar A.; Abbas N.; Saeed A. Eur. J. Med. Chem. 2014, 76, 193. |
| [8] | Fan Z.; Shi J.; Bao X. Mol. Diversity 2018, 22, 657. |
| [9] | Shi J.; Luo N.; Ding M.; Bao X. Chin. Chem. Lett. 2020, 31, 434. |
| [10] | Opoku-Temeng C.; Naclerio G.A.; Mohammad H.; Dayal N.; Abutaleb N.S.; Seleem M.N.; Sintim H.O. Eur. J. Med. Chem. 2018, 155, 797. |
| [11] | Cui Z.M.; Li Y.S.; Hu D.K.; Tian H.; Jiang J.Z.; Wang Y.; Yan X.J. Sci. Rep. 2016, 6, 20204. |
| [12] | Wu W.; Fei Q.; He J.; Liu L.; Ouyang G. Chem. Bull. 2019, 82, 74. (in Chinese) |
| [12] | 吴文能, 费强, 何军, 刘雷, 欧阳贵平, 化学通报, 2019, 82, 74.). |
| [13] | Zhang Y.; Liu X.H.; Zhan Y.Z.; Zhang L.Y.; Li Z.M.; Li Y.H.; Zhang X.; Wang B.L. Bioorg. Med. Chem. Lett. 2016, 26, 4661. |
| [14] | Wang T.; Miao W.; Wu S.; Bing G.; Zhang X.; Qin Z.; Yu H.; Qin X.; Fang J. Chin. J. Chem. 2011, 29, 959. |
| [15] | Chen J.; Chen Y.; Gan X.; Song B.; Hu D.; Song B. J. Agric. Food Chem. 2018, 66, 9616. |
| [16] | Han F.; Wan R.; Wang Y.; Wang P.; Wang J. Chin. J. Org. Chem. 2010, 30, 132. (in Chinese) |
| [16] | 韩峰, 万嵘, 王瑶, 王朋, 王锦堂, 有机化学, 2010, 30, 132.). |
| [17] | Chen X.; Gan X.; Chen J.; Chen Y.; Wang Y.; Hu D.; Song B. Chin. J. Org. Chem. 2017, 37, 2343. (in Chinese) |
| [17] | 陈学文, 甘秀海, 陈吉祥, 陈永中, 王艳娇, 胡德禹, 宋宝安, 有机化学, 2017, 37, 2343.). |
| [18] | Yan L.; Li Y.; Deng M.; Chen A.; Du Z.; Dong C.; Chen H. Chin. J. Org. Chem. 2020, 40, 731. (in Chinese) |
| [18] | 鄢龙家, 黎永良, 邓明高, 陈安超, 杜志云, 董长治, 陈惠雄, 有机化学, 2020, 40, 731.). |
| [19] | Nazir M.; Abbasi M.A.; Rehman A.; Siddiqui S.Z.; Khan K.M.; Kanwal; Salar, U.; Shahi, M.; Ashraf, M.; Lodhi, M.A.; Khan, F.A.Bioorg. Chem. 2018, 81, 253. |
| [20] | 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. |
| [21] | Luo H.; Hu D.; Wu J.; He M.; Jin L.; Yang S.; Song B. Int. J. Mol. Sci. 2012, 13, 6730. |
| [22] | Embrechts W.; Herschke F.; Pauwels F.; Stoops B.; Last S.; Pieters S.; Pande V.; Pille G.; Amssoms K.; Smyej I.; Dhuyvetter D.; Scholliers A.; Mostmans W.; Van Dijck K.; Van Schoubroeck B.; Thone T.; De Pooter D.; Fanning G.; Jonckers T. H. M.; Horton H.; Raboisson P.; McGowan D. J. Med. Chem. 2018, 61, 6236. |
| [23] | Zayed M.F.; Ihmaid S.K.; Ahmed H. E. A.; El-Adl K.; Asiri A.M.; Omar A.M. Molecules 2017, 22, 188. |
| [24] | Vitaku E.; Smith D.T.; Njadarson J.T. J. Med. Chem. 2014, 57, 10257. |
| [25] | Fan Z.; Shi J.; Luo N.; Ding M.; Bao X. J. Agric. Food Chem. 2019, 67, 11598. |
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