34602-69-2Relevant academic research and scientific papers
Synthesis, antifungal activity and QSAR of some novel carboxylic acid amides
Du, Shijie,Lu, Huizhe,Yang, Dongyan,Li, Hong,Gu, Xilin,Wan, Chuan,Jia, Changqing,Wang, Mian,Li, Xiuyun,Qin, Zhaohai
, p. 4071 - 4087 (2015/05/13)
A series of novel aromatic carboxylic acid amides were synthesized and tested for their activities against six phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to good activity. Among them N-(2-(1H-indazol-1-yl)phenyl)-2-(trifluoromethyl)benzamide (3c) exhibited the highest antifungal activity against Pythium aphanidermatum (EC50 = 16.75 μg/mL) and Rhizoctonia solani (EC50 = 19.19 μg/mL), compared to the reference compound boscalid with EC50 values of 10.68 and 14.47 μg/mL, respectively. Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were employed to develop a three-dimensional quantitative structure-activity relationship model for the activity of the compounds. In the molecular docking, a fluorine atom and the carbonyl oxygen atom of 3c formed hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173.
Synthesis, antifungal activity and structure-activity relationships of novel 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid amides
Du, Shijie,Tian, Zaimin,Yang, Dongyan,Li, Xiuyun,Li, Hong,Jia, Changqing,Che, Chuanliang,Wang, Mian,Qin, Zhaohai
, p. 8395 - 8408 (2015/05/20)
A series of novel 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid amides were synthesized and their activities were tested against seven phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to excellent activities. Among them N-(2-(5-bromo-1H-indazol-1-yl)phenyl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide (9m) exhibited higher antifungal activity against the seven phytopathogenic fungi than boscalid. Topomer CoMFA was employed to develop a three-dimensional quantitative structure-activity relationship model for the compounds. In molecular docking, the carbonyl oxygen atom of 9m could form hydrogen bonds towards the hydroxyl of TYR58 and TRP173 on SDH.
Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles
Antilla, Jon C.,Baskin, Jeremy M.,Barder, Timothy E.,Buchwald, Stephen L.
, p. 5578 - 5587 (2007/10/03)
This paper details the copper-catalyzed N-arylation of π-excessive nitrogen heterocycles. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate functional groups such as aldehydes, ketones, alcohols, primary amines, and nitriles on the aryl halide or heterocycle. Hindered aryl halides or heterocycles were also found to be suitable substrates using the conditions reported herein.
