- Design, synthesis, and fungicidal evaluation of a series of novel 5-methyl-1H-1,2,3-trizole-4-carboxyl amide and ester analogues
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Succinate dehydrogenase inhibitors (SDHIs) are efficient fungicides that are widely used to control plant diseases caused by phytopathogenic fungi, although their effectiveness is undermined by the development of resistance across a range of different fungi. One of the most common structural features of SDHIs is their amide bond. The introduction of greater structural diversity to SDHIs is a promising strategy to delay the onset of resistance. A series of novel SDHIs containing a bioactive 1,2,3-triazole moiety have been designed and synthesized and their fungicidal and insecticidal activities evaluated. The results of these analyses show that most of the newly synthesized 1,2,3-trizole-4-carboxyl amide (ester) analogues exhibit good fungicidal activities, especially towards Sclerotinia sclerotiorum, and a structure-activity relationship study confirmed that the replacement of the amide group with an ester group had little effect on fungicidal activity, which could be provideous in terms of issues and metabolism. 1,6-Dimethyl phenyl was confirmed as the most efficient substituent of the current study when it was placed on both the amide and ester compounds. Interestingly, some of the newly synthesized compounds displayed good insecticidal activities against Culex pipiens pallens. The results of the current study show that these 1,2,3-triazole-4-carboxyl amide and ester analogues represent a new type of SDHI that could be used for the development of novel pesticides.
- Wang, Zhen-Jun,Gao, Yang,Hou, Yan-Ling,Zhang, Cheng,Yu, Shu-Jing,Bian, Qiang,Li, Zheng-Ming,Zhao, Wei-Guang
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- A new and efficient procedure for preparing 1,2,3-Triazoles
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1,2,3-Triazoles are readily accessible in moderate to good yields by a diazo transfer reaction with β-amino-α,β-unsaturated ketones or esters and tosyl or mesyl azide reagent. In this methodology tile nitrogen atoms N-2 and N-3 of the triazole ring are de
- Romeiro, Gilberto A.,Pereira, Leticia O.R.,De Souza, Maria Cecilia B.V.,Ferreira, Vitor F.,Cunha, Anna Claudia
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- Synthesis of 1,2,3-Triazole Derivatives by Cyclocondensation of Alkyl Azides with Active Methylene Ketones in the System K2CO3/DMSO
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Abstract: The reaction of β-keto esters or acetylacetone with alkyl azides in the system K2CO3/DMSO proved to be a convenient method of synthesis of tri- and disubstituted 1-alkyl-1H-1,2,3-triazoles.
- Pokhodylo,Savka,Obushak
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p. 914 - 921
(2021/08/09)
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- Copper-catalyzed convenient synthesis and SAR studies of substituted-1,2,3-triazole as antimicrobial agents
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Background: A novel copper-catalyzed synthesis of substituted-1,2,3-triazole derivatives has been developed and performed by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The reaction is one-pot multicomponent. Objective: We state the advancement and execution of a methodology allowing for the synthesis of some new substituted 1,2,3-triazole analogues with antimicrobial activity. Methods: A series of triazole derivatives was synthesized by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The structures of the synthesized compounds were elucidated and confirmed by1H NMR, IR, MS and elemental analysis. All the synthesized compounds were tested for their antimicrobial activity against a series of strains of Bacillus subtilis, Staphylococcus aureus and Escherichia coli for antibacterial activity and against the strains of Candida albicans, Aspergillus flavus and Aspergillus nigar for antifungal activity, respectively. Results and Conclusion: From the antimicrobial data, it was observed that all the newly synthesized compounds showed good to moderate level of antibacterial and antifungal activity.
- Sarkate, Aniket P.,Karnik, Kshipra S.,Wakte, Pravin S.,Sarkate, Ajinkya P.,Izankar, Ashwini V.,Shinde, Devanand B.
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- Design, synthesis, and fungicidal activities of novel 5-methyl-1H-1,2,3- Trizole-4-carboxyl amide analogues
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Succinate dehydrogenase inhibitors (SDHIs) are fungicides with an amide bond widely used to control plant diseases caused by phytopathogenic fungi. Because of broad spectrum activity of new SDHIs, they have attracted wide attention from the research community. A series of structurally novel SDHIs with a bioactive 1,2,3-triazole moiety were designed and synthesized. Bioactivity screening showed that some of designed N-phenethyl-1,2,3-trizole-4-carboxyl amide analogues exhibited good fungicidal activities toward Sclerotinia sclerotiorum and Botrytis cinerea, while some of Nbenzyl- 1,2,3-trizole-4-carboxyl amide analogues exhibited good fungicidal activities toward Phytophthora capsici and Cercospora arachidicola. EC50 value of compound 5d against Cercospora arachidicola (6.6 μg/mL) was lower than that of chlorothalonil (12.3 μg/mL).
- Wang, Zhen-Jun,Yang, Hui-Hui,Tian, Lei,Zhao, Wei-Guang
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p. 290 - 295
(2016/05/11)
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- SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF
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Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.
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- SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF
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Disclosed are compounds having enhanced potency in the modulation of NMD A receptor activity. Such compounds are contemplated for use in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.
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- [Cu8(μ8-H){S2P (OEt)2} 6](PF6): A novel catalytic hydride-centered copper cluster for azide-alkyne cycloaddtion
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A hydride-centered dithiophosphate cluster [Cu8(μ 4-H){S2P(OEt)2}6](PF6) (1)] previously developed by us was applied as a new catalyst to the 1,3-dipolar cycloaddition of organic azides and
- Lee, Bo-Han,Wu, Cheng-Chieh,Fang, Xuan,Liu,Zhu, Jia-Liang
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p. 572 - 577
(2013/07/11)
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- One-pot, three-component synthesis of 1,4,5-trisubstituted 1,2,3-triazoles starting from primary alcohols
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A novel, one-pot, three-component approach for the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles through the cycloaddition of a wide range of primary alcohols with sodium azide and active methylene ketones in the presence of N-(p-toluenesulfonyl)imidazole, tetrabutylammonium iodide, and triethylamine in DMF/DMSO has been developed.
- Jin, Guanyi,Zhang, Jian,Fu, Dan,Wu, Jingjing,Cao, Song
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supporting information
p. 5446 - 5449
(2012/10/30)
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- An Improved Procedure for the Preparation of 1-Benzyl-1H-1,2,3-triazoles from Benzyl Azides.
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A procedure for the preparation of substituted 1-benzyl-1H-1,2,3-triazoles from benzyl azides under very mild conditions is described.The method provides improved yields and extends the scope of the Dimroth Reaction to other types of active methylene compound to those previously used.Benzyl azides react with active methylene compounds in dimethyl sulphoxide catalysed by potassium carbonate at 35-40 deg C to give 1H-1,2,3-triazoles usually in good yield.Acetonitrile derivatives gave 5-amino-1H-1,2,3-triazoles whereas diethyl malonate gave 5-hydroxy-1H-1,2,3-triazoles. 1H-1,2,3-Triazole-4-carboxylate esters and 1H-1,2,3-triazole-4-ketones were obtained from ethyl acetoacetate and β-diketones respectively.Benzyl methyl ketone reacted to give 5-methyl-4-phenyl-1H-1,2,3-triazole, but acetone and acetophenone failed to react.Other active methylene compounds which did not react under these reaction conditions included ethyl cyanoacetate, ethyl fluoroacetate and ethyl nitroacetate.
- Cottrell, Ian F.,Hands, David,Houghton, Peter G.,Humphrey, Guy R.,Wright, Stanley H. B.
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p. 301 - 304
(2007/10/02)
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