- Synthesis and Antifungal Activity of Novel Furan-2,4-dione Derivatives Containing Substituted Phenylhydrazine Moiety
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A series of novel 3-(2-(substituted phenyl)hydrazinylmethylidene)furan-2,4(3H,5H)-diones were designed and synthesized with ethyl 4-chloroacetoacetate as the starting material. Their structures were confirmed by FT-IR, 1H NMR, 13C NMR, EI-MS and elemental analysis. Bioassay data demonstrated that these compounds exhibited remarkable antifungal activity against Fusarium graminearum, Botrytis cinerea, Rhizoctonia cerealis and Colletotrichum capsici. Compound 3-(2-(4-bromophenyl)hydrazinylmethylidene)furan-2,4(3H,5H)-dione (5g) had excellent bioactivity against Botrytis cinerea with an EC50 value of 0.18 μg/mL - markedly lower than the 0.24 μg/mL of the commercial fungicide procymidone. The result revealed that introducing the halogenated phenylhydrazine at the 3-position of furan-2,4(3H, 5H)-dione was an effective way to design new tetronic acid derivatives as new fungicides. A series of novel furan-2,4-dione derivatives containing a substituted phenylhydrazine moiety were designed and synthesized. These compounds exhibited remarkable antifungal activity against Fusarium graminearum, Botrytis cinerea, Rhizoctonia cerealis and Colletotrichum capsici. Compound 5g showed significantly better bioactivity than the control fungicides.
- Hu, Ying,Zhang, Li-Zhi,Ren, Zheng-Jiao,Zhao, Zheng,Xu, Wen-Qin,Yang, Chun-Long
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Read Online
- A process for preparing swiss that Wei intermediates (by machine translation)
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The invention discloses a method for preparing swiss that Wei intermediates of the method, the method condensable acetyl acetic acid ethyl ester as the raw material, after 4 step reaction to obtain the key swiss that Wei middle style I compound. The method has reasonable process, the operation is simple, low cost, high yield, through this method can better realize the industrialization, the production efficiency is improved. (by machine translation)
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Paragraph 0017
(2017/09/01)
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- Synthesis, characterization, antifungal evaluation and 3D-QSAR study of phenylhydrazine substituted tetronic acid derivatives
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A series of 3-(1-(2-(substituted phenyl)hydrazinyl)alkylidene)furan-2,4(3H, 5H)-diones were designed and prepared using two synthetic routes. Their structures were confirmed by FT-IR, 1H NMR, 13C NMR, MS, elemental analysis and single-crystal X-ray diffraction. Their bioactivity was evaluated against Botrytis cinerea in vitro. Most target compounds exhibited remarkable antifungal activity. Two compounds 7f and 7h were highly effective and their EC50 values were 0.241 μg/mL and 0.167 μg/mL, respectively, close to that of the control drug procymidone. 3D-QSAR studies of CoMFA and CoMSIA were carried out. Models with good predictive ability were generated with the cross validated q2 values for CoMFA and CoMSIA being 0.565 and 0.823. Conventional r2 values were 0.983 and 0.945, respectively. The results provided a practical tool for guiding the design and synthesis of novel and more potent tetronic acid derivatives containing substituted phenylhydrazine moiety.
- Hu, Ying,Wang, Junjun,Lu, Aimin,Yang, Chunlong
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supporting information
p. 3772 - 3776
(2014/09/17)
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- Synthesis and comparative evaluation of 4-oxa- and 4-aza-podophyllotoxins as antiproliferative microtubule destabilizing agents
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A series of novel 4-oxa-podophyllotoxin derivatives 7 featuring the intact lactone ring D and various substituents in rings B and E has been synthesized and evaluated in a phenotypic sea urchin embryo assay along with the representative 4-aza-analogs 5 for their antimitotic and microtubule destabilizing activity. The most active compounds exhibited myristicin-derived or a 3′,5′-dimethoxy substitution pattern in the ring E and a 6-methoxy moiety replacing the methylenedioxy ring A. Compounds 5xb, 5xe, 5yb, 7xa, 7xb, and 7xc showed potent antiproliferative effects in the NCI60 cytotoxicity screen. Notably, growth of the multi-drug resistant NCI/ADR-RES cells was more affected by these agents than the parent OVCAR-8 cell line. Although generally 4-oxa-podophyllotoxins were less potent than the respective 4-aza-derivatives in these assays, stability of the former series towards oxidation may prove to be of interest for the development of anticancer agents with in vivo activity.
- Chernysheva, Natalia B.,Tsyganov, Dmitry V.,Philchenkov, Alex A.,Zavelevich, Michael P.,Kiselyov, Alex S.,Semenov, Roman V.,Semenova, Marina N.,Semenov, Victor V.
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scheme or table
p. 2590 - 2593
(2012/05/05)
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- Methods of inhibiting the advanced glycosylation of proteins using tetramic and tetronic acids and compositions therefor
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The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises substituted or unsubstituted tetramic and tetronic acids capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with a carbonyl moiety of an early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.
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- Inhibitors of the advanced glycosylation of proteins and methods of use therefor
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The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises an agent capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with a carbonyl moiety of an early glycosylation product of such target proteins resulting from their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.
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- Mechanism of hydrolysis and structure-stability relationship of enaminones as potential prodrugs of model primary amines
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The objective of this work was to investigate the chemistry and the structure-stability relationship of enaminones (a class of enamines formed between a primary amine and a 1,3-dicarbonyl compound) and to evaluate their potential usefulness as prodrugs of primary amines. The acid-catalyzed degradation of the enaminones was found to be very sensitive to minor differences in the structure of the 1,3-dicarbonyl compound used to form the enaminone, but relatively insensitive to changes in the amine portion of the enaminones. A correlation was found between the rate of enaminone hydrolysis and the pK(a) of the 1,3-dicarbonyl compound, suggesting that the rate-controlling step in the hydrolysis of the enaminones was the proton addition to the vinyl carbon of the enaminone. Enaminones formed with cyclic 1,3-dicarbonyl compounds were significantly more stable than those formed with structurally similar acyclic compounds. Based on chemical stability considerations alone, enaminones do not appear to be good candidates as prodrugs of primary amines. Evidence is presented, however, that enaminones formed between amines and 1,3-ketoesters or lactones may be subject to enzyme-catalyzed degradation. Further research on the design of enaminones destabilized by a triggering enzymatic event that results in the loss of conjugation (e.g., ester or lactone hydrolysis or an oxidation/reduction event) may prove worth pursuing.
- Naringrekar,Stella
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p. 138 - 146
(2007/10/02)
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