18212-20-9Relevant articles and documents
Design and synthesis of novel cylopentapyrazoles bearing 1,2,3-thiadiazole moiety as potent antifungal agents
Giray, Betül,Karada?, Ay?e Esra,?pek, ?zgecan ?avlu?,Pekel, Hanife,Güzel, Mustafa,Kü?ük, Hatice Ba?p?nar
, (2020)
In drug-resistant phytopathogenic fungi, there has been extensive research on microbiological and antifungal drug development. In this study, a novel series of cylopentapyrazole bearing a 1,2,3-thiadiazole ring 2a-e were designed and synthesized according to the principle of combination of bioactive structures. Thus, we have employed a [3 + 2] cycloaddition with 4-methyl-[1,2,3] thiadiazole-5-carboxylic acid hydrazones 1a-e and cyclopentadiene ring. Novel synthesized compounds were identified with IR, 1H and 13C NMR, mass spectrometry and elemental analysis then, antifungal activities were assayed. Based on our study, a combination of the compounds 1a and 2b possess remarkable antifungal activity against Botrytis cinerea AHU 9424 with 100% inhibition. EC50 values were calculated by studying different doses in combinations with high inhibition rates. The combination of 1a + 2b has an EC50 value at 6.37 and 13.85 μg/ml concentrations against B. cinerea and F. culmorum, respectively. The combination of compound 1a + 2b, having a cylopentapyrazole ring on the 1,2,3-thiadiazole backbone, shows promising fungicidal activity and deserves further development. Additionally, the homology model of the CYP51 enzyme that belongs to Fusarium moniliforme was generated using CYP51B (PDB ID: 6CR2), and molecular docking was performed using this homology model for each compound. The results of this study clearly indicate that these novel compounds can be identified as promising lead compounds and potential fungicidal agents in future.
Traceless solid-phase synthesis of 1,2,3-thiadiazole derivatives from resin-bound acylhydrazine
Liu, Zhanxiang,Mu, Yuanyuan,Lin, Jie,Chen, Yiya
, p. 4407 - 4414 (2008)
A novel synthesis of 1,2,3-thiadiazole derivatives using a traceless solid-phase approach is described, in which many kinds of 1,2,3-thiadiazole derivatives were efficiently obtained in good yields and high purities via traceless cyclization cleavage of resin-bound acylhydrazones with thionyl chloride. Copyright Taylor & Francis Group, LLC.
Synthesis and biological activities of (E)-β-farnesene analogues containing 1,2,3-thiadiazole
Zhang, Jing-Peng,Qin, Yao-Guo,Dong, Ya-Wen,Song, Dun-Lun,Duan, Hong-Xia,Yang, Xin-Ling
, p. 372 - 376 (2017)
In order to discover novel compounds with high-activity to control aphid, a series of novel (E)-β-farnesene analogues containing 1,2,3-thiadiazole were designed and synthesized, and their structures were confirmed by IR,1H NMR,13C NMR, and HRMS (ESI). The stability of representative compounds was studied by HPLC and1H NMR techniques. Repellent activity results indicated that compounds 8h and 8j displayed 60.3% and 62.0% repellent rates, respectively. The aphicidal bioassay results showed that most analogues exhibited considerable aphicidal activity against Myzus persicae. Especially, analogues 8l, 8s and 8t exhibited high activity with LC50values of 33.4?μg/mL, 50.2?μg/mL and 61.8?μg/mL, respectively, which were higher than the lead compound (E)-β-farnesene, but lower than commercial insecticide pymetrozine with a LC50of 7.1?μg/mL.
Design, synthesis, and evaluation of substituted 2-acylamide-1,3-benzo[d]zole analogues as agents against MDR- and XDR-MTB
Li, Dongsheng,Liu, Chao,Jiang, Xinhai,Lin, Yuan,Zhang, Jing,Li, Yan,You, Xuefu,Jiang, Wei,Chen, Minghua,Xu, Yanni,Si, Shuyi
, (2020/10/21)
N-(5-Chlorobenzo[d]oxazol-2-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamideox-amide has been identified as a potent inhibitor of Mtb H37Rv, with a minimum inhibitory concentration (MIC) of 0.42 μM. In this study, a series of substituted 2-acylamide-1,3-zole analogues were designed and synthesized, and their anti-Mtb activities were analyzed. In total, 17 compounds were found to be potent anti-Mtb agents, especially against the MDR- and XDR-MTB strains, with MIC values 10 μM. These analogues can inhibit both drug-sensitive and drug-resistant Mtb. Four representative compounds were selected for further profiling, and the results indicate that compound 18 is acceptably safe and has favorable pharmacokinetic (PK) properties. In addition, this compound displays potent activity against Gram-positive bacteria, with MIC values in the range of 1.48–11.86 μM. The data obtained herein suggest that promising anti-Mtb candidates may be developed via structural modification, and that further research is needed to explore other compounds.
