Semisynthesis and Antibacterial Activity of 7β-[2-(2-Aminothiazol-4- yl)-(Z)-2-methoxyiminoacetylamido]-3-heterothiomethyl-cephalosporins

Abstract

New cephalosporin derivatives 5a～5j were prepared by condensation of 3a～3j with aminothiazoleoxime active ester 4. The intermediates 3a～3j were synthesized by the reaction of 5-substituted-1,3,4- oxadiazole-2-thiols (2a～2h), 5-arylamino-1,3,4-thiadiazole-2-thiols (2i～2j) with 7-aminocephalosporanic acid (7-ACA), respectively. The preliminary results of antibacterial activities revealed that compounds 5 showed obviously antibacterial activities against both Gram-positive and Gram-negative bacteria.

Key words: centrifugal-TLC, semisynthesis, antibacterial activity, cephalosporin

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HUI Xin-Ping*^,a,WANG Qin^b,WANG Fang^b,ZHANG Zi-Yi*^,a,GUAN Zuo-Wu^c. Semisynthesis and Antibacterial Activity of 7β-[2-(2-Aminothiazol-4- yl)-(Z)-2-methoxyiminoacetylamido]-3-heterothiomethyl-cephalosporins[J]. Chin. J. Org. Chem., 2006, 26(12): 1704-1708.

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7β-[2-(2-氨噻唑-4-基)-(Z)-2-甲氧亚胺乙酰胺基]-3-杂环硫亚甲基头孢菌素衍生物的半合成及抗菌活性

Semisynthesis and Antibacterial Activity of 7β-[2-(2-Aminothiazol-4- yl)-(Z)-2-methoxyiminoacetylamido]-3-heterothiomethyl-cephalosporins

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[1]	Haibo Huo, Guixia Li, Shijun Wang, Chun Han, Baojun Shi, Jian Li. Novel γ-Carboline Derivatives as Antibacterial Agents: Synthesis and Antibacterial Evaluation [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 204-215.
[2]	Weizhong Ding, Bingwen Zhang, Yanqing Xue, Yuqi Lin, Zhijun Tang, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. A New Polyketide from Fusarium graminearum [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3319-3322.
[3]	Yifang Chen, Xin Luo, Yu Wang, Zhifu Xing, Ju Peng, Jixiang Chen. Design, Synthesis and Antibacterial Activity of 1,3,4-Oxadiazole Sufones Containing Sulfonamide Structure [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 274-284.
[4]	Dan Huang, Xuhua Nong, Jianni Yang, Chen Li, Changri Han, Guangying Chen, Xiaoping Song, Zhenfan Sun, Yang Hui, Wenhao Chen. Study on the Secondary Metabolites of the Endophytic Fungus Aspergillus terreus HQ100X-1 in Scutellaria formosana [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2961-2966.
[5]	Huanhuan Wang, Pu Yang, Hongjin Zhai, Shuo Zhang, Yaquan Cao, Yingxue Yang, Chunli Wu. Design, Synthesis and Activity Evaluation of New Tylosin Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 557-572.
[6]	Ali Dai, Renfeng Zhang, Chuanhui Li, Lijiao Yu, Ya Wang, Jian Wu. Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3633-3642.
[7]	Feng He, Shengxin Guo, Ali Dai, Renfeng Zhang, Jian Wu. Synthesis, Characterization, and Biological Activity of Novel Amide Derivatives Containing Trifluoromethylpyridine Moieties [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3303-3311.
[8]	Shao Lihui, Gan Yiyuan, Hou Mi, Tao Shilin, Zhang Liqiong, Wang Zhenchao, Ouyang Guiping. Design, Synthesis and Biological Activity of Quinazolinone Derivatives Containing Hydrazone Structural Units [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1975-1982.
[9]	Li Yongkun, Tang Yanling, Li Minxin, Yang Xiaobi, Gao Hui, Mao Zewei. Synthesis and Antibacterial Activity of Thienyl Chalcone Derivatives Bearing Piperazine Moiety [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 108-114.
[10]	Fu Lin, Sun Bingxia, Zhai Jiadai, Li Yuanyuan, Liu Xinqiang, Song Ru, Shi Guanqun, Li Jiaona, Song Yuanxia, Sang Feng. Synthesis and Antibacterial Activity Study of Natural 5'-Hydroxyisoprenyl Chalcones [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 201-208.
[11]	He Wenjing, Liu Denyue, Gan Xiuhai, Zhang Jian, Liu Zhengjun, Yi Chongfen, Song Bao'an. Synthesis and Biological Activity of Novel 1,3,4-Thiadiazolo[3,2-a]pyrimidinone Mesoionic Derivatives [J]. Chin. J. Org. Chem., 2019, 39(8): 2287-2294.
[12]	Ding Chengrong, Pan Yayun, Yin Xu, Tan Chengxia. Synthesis and Biological Activity of Thiazolidine Piperidine Nicotinamide Compounds [J]. Chin. J. Org. Chem., 2019, 39(7): 2099-2105.
[13]	Mei Rongqing, Huang Guolei, Wang Bin, Bai Meng, Luo Youping, Chen Guangying, Zheng Caijuan. Two New Isocoumarins Isolated from a Mangrove-Derived Fungus Penicillium citrinum HL-5126 [J]. Chin. J. Org. Chem., 2019, 39(5): 1479-1482.
[14]	Liu Haishan, Zhu Guoliang, Zhao Shuige, Fu Peng, Zhu Weiming. Bioactive Natural Products from the Marine Sponge-Derived Nocardiopsis dassonvillei OUCMDZ-4534 [J]. Chin. J. Org. Chem., 2019, 39(2): 507-514.
[15]	Guo Yongtai, Hou Xiyan, Zheng Changji, Zhao Chunhui, Jin Yuting, Gao Xueqin, Wang Qian, Sun Lei, Zhao Longxuan, Piao Hua. Synthesis, Characteristics and Bioactivities of Novel Isosteviol Derivatives [J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3532-3541.