4744-71-2Relevant articles and documents
Synthesis, Bioactivity Evaluation, 3D-QSAR, and Molecular Docking of Novel Pyrazole-4-carbohydrazides as Potential Fungicides Targeting Succinate Dehydrogenase
Jiao, Jian,Chen, Min,Sun, Shengxin,Si, Weijie,Wang, Xiaobin,Ding, Weijie,Fu, Xincan,Wang, An,Yang, Chunlong
, p. 323 - 329 (2021)
To screen novel antifungal agents targeting the succinate dehydrogenase (SDH), a series of pyrazole-4-carbohydrazides were rationally designed, synthesized, and characterized under the guidance of the structures of succinate dehydrogenase inhibitors (SDHIs). Bioassay results in vitro indicated that most of the target compounds exhibited excellent activity against Rhizoctonia solani (R. solani), Fusarium graminearum (F. graminearum), Botrytis cinerea (B. cinerea) and Colletotrichum capsica (C. cinerea). Compounds 7d, 7l, 7t and 7x were identified as the most promoting candidates, and their anti-F. graminearum EC50 values were as low as 0.56, 0.47, 0.46 and 0.49 μg/mL, respectively, presenting the similar antifungal activity as that of the commonly used fungicide carbendazim (0.43 μg/mL). The 3D-QSAR models were built for a systematic structure-activity relationship profile to explore more potent pyrazole-4-carbohydrazides as novel fungicides. Molecular docking of 7d, 7l and 7r with SDH was performed to reveal the binding modes in active pocket and analyze the interactions between the molecules and the SDH protein.
Novel 5-chloro-pyrazole derivatives containing a phenylhydrazone moiety as potent antifungal agents: synthesis, crystal structure, biological evaluation and a 3D-QSAR study
Jiao, Jian,Wang, An,Chen, Min,Wang, Meng-Qi,Yang, Chun-Long
, p. 6350 - 6360 (2019/04/25)
Based on the active substructure combination principle, twenty-four novel 5-chloro-pyrazole derivatives containing a phenylhydrazone moiety were designed, synthesized, and evaluated for their antifungal activity. Their structures were confirmed using 1H NMR, 13C NMR, and HR-MS spectra. The single-crystal structure of compound 8a was analyzed emphatically using X-ray diffraction. The antifungal activities against Fusarium graminearum, Botrytis cinerea, and Rhizoctonia solani were evaluated in vitro. The results of the bioassays revealed that most of the target compounds showed obvious fungicidal activity. Strikingly, the compound 7c exhibited the most potent activity with EC50 values of 0.74, 0.68, and 0.85 μg mL?1 against the above three plant pathogenic fungi, respectively. The compounds 7c, 8d, and 8g showed significant bioactivity against R. solani with EC50 values of 0.85, 0.25, and 0.96 μg mL?1, respectively. In addition, CoMFA and CoMSIA molecular modeling was performed for a 3D-QSAR study, and presented a good predictive ability with q2 values of 0.575 and 0.667, and r2 values of 0.961 and 0.962, respectively. The results provide useful information for guiding the design and synthesis of novel potent pyrazole derivatives with good antifungal activity.
Synthesis and crystal structure of some 3,5-pyrazolidinediones
Metwally, Saoud A.M.,Moneim, Maisa I. Abdel,Elossely, Yasser A.,Awad, Radwa I.,Abou-Hadeed, Khaled
, p. 426 - 437 (2014/05/06)
Syntheses of various derivatives of 3,5-pyrazolidenedione are reported. This includes 4-arylidene (alkylidene or aralkylidene)-3,5-pyrazolidinediones, which on epoxidation gave unreported oxiranes. The syntheses of these derivatives were based on either the Knoevenagel reaction of carbonyl derivatives with 3,4-pyrazolidinedione or cyclization of arylidene (alkylidene) malonic acid hydrazide with glacial acetic acid. 4-Arylazo-3,5-pyrazolidinedione derivatives were also prepared by coupling of aryldiazonium salts with 3,5-pyrazolidinedione or cyclization of arylazomalonic acid hydrazide. Reduction of 4-benzylidene derivatives gave the corresponding benzyl derivatives. The structure of the new products was confirmed by elemental and spectral analyses and X-ray crystallography.
