4744-71-2Relevant academic research and scientific papers
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.
A new approach for one-pot, green synthesis of new polycyclic indoles in aqueous solution
Ameri, Mohsen,Asghari, Alireza,Amoozadeh, Ali,Bakherad, Mohammad
, p. 1031 - 1034 (2017/05/22)
Electro-oxidation of phenylamine derivatives (1a and 1b) have been studied in the presence of pyrazolidine-3,5-dione (3) as a nucleophile in phosphate buffer solution mixed with ethanol, using voltammetric and spectroscopic techniques. The obtained results indicated that the oxidized form of phenylamines (2a and 2b) participate in Michael addition type reactions with pyrazolidine-3,5-dione (3) and via ECECCCCC mechanisms convert to the corresponding new polycyclic indoles (12a and 12b). In the present study, new polycyclic indole derivatives were synthesized with good yields and high purity using a facile, one-pot and environmentally friendly electrochemical method, without any chemical catalysts, toxic solvents and hard conditions.
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.
PYRAZOLIDINEDIONE DERIVATIVES AND THEIR USE AS PLATELET AGGREGATION INHIBITORS
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Page 63, (2010/02/10)
Pyrazolidinedione derivatives of the general formula (I), wherein R1 is hydrogen, optionally substituted alkyl, cycloalkyl, aryl, arylalkyl, heteroaryl or heteroarylalkyl; and R2 is aryl or heteroaryl; tautomers thereof; geometric is
Conversions of coumarins accompanied by intermediate opening and recyclization of the lactone ring. 2. Study of the interaction of malonic acid hydrazide and amide derivatives with 3-acyl(3-cyano, 3-ethoxycarbonyl)coumarins
Nemeryuk,Dimitrova,Anisimova,Sedov,Solov'eva,Traven
, p. 1255 - 1266 (2007/10/03)
Reaction between the N,N′-diisopropylidene and N,N′-diacetyl derivatives of malonic acid dihydrazide and 3-acyl(3-cyano, 3-ethoxycarbonyl) coumarins under the conditions of the Michael reaction lead to the formation of N′-isopropylidene and N′-acetyl derivatives of coumarin-3-carboxylic acid hydrazide. Ethoxycarbonylacethydrazide reacts in an analogous manner. Special features have been studied of the interaction of malonic acid amide derivatives with unsubstituted coumarin and with coumarins containing electron-withdrawing groupings in position 3 of the ring. 2005 Springer Science+Business Media, Inc.
Synthesis of Unsubstituted Pyrazolidine-3,5-dione
Dubau, Franz-Peter
, p. 2714 - 2716 (2007/10/02)
The cyclisation of (ethoxycarbonyl)acetohydrazide (1) with sodium methylate led to pyrazolidine-3,5-dione (2).The proof of this substance could be shown by a chemical way; for this product reacted with 6 to the same compound 5 as 3 and 4.Another transfer
Ring Transformation of 3,1-Benzothiazin-2,4-dithiones with Carboxylic Acid Hydrazides to Substituted 1,3,4-Thiadiazoles or in the Presence of Hydroxid Ions to 3-Acylamino-quinazolin-2,4-dithiones
Leistner, Siegfried,Hentschel, Karin,Wagner, Guenther
, p. 915 - 922 (2007/10/02)
The substituted 1,3,4-thiadiazoles 4-14 were prepared in one step by reaction of 3,1 benzothiazin-2,4-dithiones 1 and 3 with RCONHNH2 (R=Me, Ph, substituted Ph, 4-Pyridyl, CONHNH2).Reaction of 1 with RCONHNH2 in the presence of HO(-) leads to substituted quinazolin-2,4-dithiones 18-20.Under the action of CS2 the yield of 19 and 20 increases.Possible reaction mechanisms are discussed. - keywords: 2H-3,1-Benzothiazin-2,4(1H)-dithione; Carbocyclic acid hydrazides; Quinazolin-2,4(1H,3H)-dithione; Ring transformation; 1,3,4-Thiadiazoles
