Synthesis and biological evaluation of dihydrotriazine derivatives as potential antibacterial agents
- Corresponding author: Zheng Chang-Ji, zhengcj@ybu.edu.cn Piao Hu-Ri, piaohr@ybu.edu.cn 1These authors contributed equally to this work.
Citation: Zhang Tian-Yi, Li Chao, Tian Yu-Shun, Li Jia-Jun, Sun Liang-Peng, Zheng Chang-Ji, Piao Hu-Ri. Synthesis and biological evaluation of dihydrotriazine derivatives as potential antibacterial agents[J]. Chinese Chemical Letters, ;2017, 28(8): 1737-1742. doi: 10.1016/j.cclet.2017.05.022
Pendleton J.N., Gorman S.P., Gilmore B.F.. Clinical relevance of the ESKAPE pathogens[J]. Expert Rev. Anti-Infect. Ther., 2013,11:297-308. doi: 10.1586/eri.13.12
Fischbach M.A., Walsh C.T.. Antibiotics for emerging pathogens[J]. Science, 2009,325:1089-1093. doi: 10.1126/science.1176667
Khalafi A., Nezhad -, Soltani Rad M.N., Mohabatkar H., Asrari Z.. B. Hemmateenejad[J]. Bioorg. Med. Chem., 2005,13:1931-1938. doi: 10.1016/j.bmc.2005.01.014
Schweitzer B.I., Dicker A.P., Bertino J.R.. Dihydrofolate reductase as a therapeutic target[J]. FASEB J. Off. Publ. Fed. Am. Soc. Exp. Biol., 1990,4:2441-2452.
Blaney J.M., Silipo C., Vittoria A.. Structure-activity relationships of dihydrofolate reductase inhibitors[J]. Chem. Rev., 1984,84:333-407. doi: 10.1021/cr00062a002
Feng J.H., Ding T., Ju X.L.. Synthesis and fungicidal activity of novel 1, 3, 5-triazine derivatives[J]. J. Wuhan Inst. Tech., 2013,35:35-38.
Singha B., Bhata H.R., Kumawatb M.K.. Structure-guided discovery of 1, 3, 5-triazine-pyrazole conjugates as antibacterial and antibiofilm agent against pathogens causing human diseases with favorable metabolic fate[J]. Bioorg. Med. Chem. Lett., 2014,24:3321-3325. doi: 10.1016/j.bmcl.2014.05.103
Chen Z.H., Zheng C.J., Sun L.P., Piao H.R.. Synthesis of new chalcone derivatives containing a rhodanine-3-acetic acid moiety with potential anti-bacterial activity[J]. Eur. J. Med. Chem., 2010,45:5739-5743. doi: 10.1016/j.ejmech.2010.09.031
Song M.X., Zheng C.J., Deng X.Q.. Synthesis and bioactivity evaluation of rhodanine derivatives as potential anti-bacterial agents[J]. Eur. J. Med. Chem., 2012,54:403-412. doi: 10.1016/j.ejmech.2012.05.023
Jin X., Zheng C.J., Song M.X.. Synthesis and antimicrobial evaluation of Lphenylalanine-derived C5-substituted rhodanine and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone[J]. Eur. J. Med. Chem., 2012,56:203-209. doi: 10.1016/j.ejmech.2012.08.026
Miao J., Zheng C.J., Sun L.P.. Synthesis and potential antibacterial activity of new rhodanine-3-acetic acid derivatives[J]. Med. Chem. Res., 2013,22:4125-4132. doi: 10.1007/s00044-012-0417-z
Song M.X., Zheng C.J., Deng X.Q., Wei Z.Y., Piao H.R.. The synthesis and antibacterial activities of N-carboxymethyl rhodanines[J]. Med. Chem., 2014,4:441-448.
Wei Z.Y., Chi K.Q., Yu Z.K.. Synthesis and biological evaluation of chalcone derivatives containing aminoguanidine or acylhydrazone moieties[J]. Bioorg. Med. Chem. Lett., 2016,26:5920-5925. doi: 10.1016/j.bmcl.2016.11.001
Oefner C., Bandera M., Haldimann A.. Increased hydrophobic interactions of iclaprim with Staphylococcus aureus dihydrofolate reductase are responsible for the increase in affinity and antibacterial activity[J]. J. Antimicrob. Chemother., 2009,63:687-698. doi: 10.1093/jac/dkp024
Lam T., Hilgers M.T., Cunningham M.L.. Structure-Based design of new dihydrofolate reductase antibacterial agents:7-(benzimidazol-1-yl)-2, 4-diaminoquinazolines[J]. J. Med. Chem., 2014,57:651-668. doi: 10.1021/jm401204g
Won S.J., Liu C.T., Tsao L.T.. Synthetic chalcones as potential antiinflammatory and cancer chemopreventive agents[J]. Eur. J. Med. Chem., 2005,40:103-112. doi: 10.1016/j.ejmech.2004.09.006
Jin Wang , Xiaoyan Pan , Junyu Zhang , Qingqing Zhang , Yanchen Li , Weiwei Guo , Jie Zhang . Active molecule-based theranostic agents for tumor vasculature normalization and antitumor efficacy. Chinese Chemical Letters, 2024, 35(8): 109187-. doi: 10.1016/j.cclet.2023.109187
Chuan Li , Yangyang Han , Yanan Zhai , Ke Li , Xingzhong Liu , Zhuan Zhang , Cai Jia , Yongsheng Che . Phomaketals A and B, pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.. Chinese Chemical Letters, 2024, 35(7): 109019-. doi: 10.1016/j.cclet.2023.109019
Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
Jing JIN , Zhuming GUO , Zhiyin XIAO , Xiujuan JIANG , Yi HE , Xiaoming LIU . Tuning the stability and cytotoxicity of fac-[Fe(CO)3I3]- anion by its counter ions: From aminiums to inorganic cations. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 991-1004. doi: 10.11862/CJIC.20230458
Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
Jinjie Lu , Qikai Liu , Yuting Zhang , Yi Zhou , Yanbo Zhou . Antibacterial performance of cationic quaternary phosphonium-modified chitosan polymer in water. Chinese Chemical Letters, 2024, 35(9): 109406-. doi: 10.1016/j.cclet.2023.109406
Luyao Lu , Chen Zhu , Fei Li , Pu Wang , Xi Kang , Yong Pei , Manzhou Zhu . Ligand effects on geometric structures and catalytic activities of atomically precise copper nanoclusters. Chinese Journal of Structural Chemistry, 2024, 43(10): 100411-100411. doi: 10.1016/j.cjsc.2024.100411
Xingyu Chen , Sihui Zhuang , Weiyao Yan , Zhengli Zeng , Jianguo Feng , Hongen Cao , Lei Yu . Synthesis, antibacterial evaluation, and safety assessment of Se@PLA as a potent bactericide against Xanthomonas oryzae pv. oryzae. Chinese Chemical Letters, 2024, 35(10): 109635-. doi: 10.1016/j.cclet.2024.109635
Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
Ji Zhang , Tong Zhang , Qiao An , Peng Zhang , Cai-Yan Tian , Chun-Mao Yuan , Ping Yi , Zhan-Xing Hu , Xiao-Jiang Hao . Five quinolizidine alkaloids with anti-tobacco mosaic virus activities from two species of Sophora. Chinese Chemical Letters, 2024, 35(6): 108927-. doi: 10.1016/j.cclet.2023.108927
Ting Li , Xinxin Zheng , Lejing Qu , Yuanyuan Ou , Sai Qiao , Xue Zhao , Yajun Zhang , Xinfeng Zhao , Qian Li . A chromatographic method for pursuing potential GPCR ligands with the capacity to characterize their intrinsic activities of regulating downstream signaling pathway. Chinese Chemical Letters, 2024, 35(10): 109792-. doi: 10.1016/j.cclet.2024.109792
Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
An Lu , Yuhao Guo , Yi Yan , Lin Zhai , Xiangyu Wang , Weiran Cao , Zijie Li , Zhixia Zhao , Yujie Shi , Yuanjun Zhu , Xiaoyan Liu , Huining He , Zhiyu Wang , Jian-Cheng Wang . Nanomedicine integrating the lipidic derivative of 5-fluorouracil, miriplatin and PD-L1 siRNA for enhancing tumor therapy. Chinese Chemical Letters, 2024, 35(6): 108928-. doi: 10.1016/j.cclet.2023.108928
Keke Han , Wenjun Rao , Xiuli You , Haina Zhang , Xing Ye , Zhenhong Wei , Hu Cai . Two new high-temperature molecular ferroelectrics [1,5-3.2.2-Hdabcni]X (X = ClO4−, ReO4−). Chinese Chemical Letters, 2024, 35(6): 108809-. doi: 10.1016/j.cclet.2023.108809
Jiahui Li , Qiao Shi , Ying Xue , Mingde Zheng , Long Liu , Tuoyu Geng , Daoqing Gong , Minmeng Zhao . The effects of in ovo feeding of selenized glucose on liver selenium concentration and antioxidant capacity in neonatal broilers. Chinese Chemical Letters, 2024, 35(6): 109239-. doi: 10.1016/j.cclet.2023.109239
Zhe Wang , Li-Peng Hou , Qian-Kui Zhang , Nan Yao , Aibing Chen , Jia-Qi Huang , Xue-Qiang Zhang . High-performance localized high-concentration electrolytes by diluent design for long-cycling lithium metal batteries. Chinese Chemical Letters, 2024, 35(4): 108570-. doi: 10.1016/j.cclet.2023.108570
Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn2+ doped quasi-two-dimensional perovskites (PEA)2PbyMn1-yBr4. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250