60287-67-4Relevant articles and documents
Design, synthesis and antifungal activity of novel furancarboxamide derivatives
Wen, Fang,Jin, Hong,Tao, Ke,Hou, Taiping
, p. 244 - 251 (2016/05/24)
Twenty-seven novel furancarboxamide derivatives with a diphenyl ether moiety were synthesized and evaluated for their antifungal activity against Rhizoctonia solani, Botrytis cirerea, Valsa Mali and Sphaceloma ampelimum. Antifungal bioassay results indicated that most compounds had good or excellent fungicidal activities for R. solani and S. ampelimum at 20 mg L-1. Among synthesized compounds, compound 18e showed a greater inhibitory effect against S. ampelimum, with half maximal effective concentration (EC50) values of 0.020 mg L-1. This strong activity rivals currently used commercial fungicides, such as Boscalid and Carbendazim, and has great potential as a lead compound for future development of novel fungicides.
Additivity of substituent effects in aromatic stacking interactions
Hwang, Jungwun,Li, Ping,Carroll, William R.,Smith, Mark D.,Pellechia, Perry J.,Shimizu, Ken D.
, p. 14060 - 14067 (2015/01/08)
The goal of this study was to experimentally test the additivity of the electrostatic substituent effects (SEs) for the aromatic stacking interaction. The additivity of the SEs was assessed using a small molecule model system that could adopt an offset face-to-face aromatic stacking geometry. The intramolecular interactions of these molecular torsional balances were quantitatively measured via the changes in a folded/unfolded conformational equilibrium. Five different types of substituents were examined (CH3, OCH3, Cl, CN, and NO2) that ranged from electron-donating to electron-withdrawing. The strength of the intramolecular stacking interactions was measured for 21 substituted aromatic stacking balances and 21 control balances in chloroform solution. The observed stability trends were consistent with additive SEs. Specifically, additive SE models could predict SEs with an accuracy from ±0.01 to ±0.02 kcal/mol. The additive SEs were consistent with Wheeler and Houk's direct SE model. However, the indirect or polarization SE model cannot be ruled out as it shows similar levels of additivity for two to three substituent systems, which were the number of substituents in our model system. SE additivity also has practical utility as the SEs can be accurately predicted. This should aid in the rational design and optimization of systems that utilize aromatic stacking interactions.
Structure-based design of caspase-1 inhibitor containing a diphenyl ether sulfonamide
Shahripour, Aurash B,Plummer, Mark S,Lunney, Elizabeth A,Sawyer, Tomi K,Stankovic, Charles J,Connolly, Michael K,Rubin, John R,Walker, Nigel P.C,Brady, Kenneth D,Allen, Hamish J,Talanian, Robert V,Wong, Winnie W,Humblet, Christine
, p. 2779 - 2782 (2007/10/03)
A series of compounds was designed and prepared as inhibitors of interleukin-1β converting enzyme (ICE), also known as caspase-1. These inhibitors, which employ a diphenyl ether sulfonamide, were designed to improve potency by forming favorable interactions between the diphenyl ether rings and the prime side hydrophobic region. An X-ray crystal structure of a representative member of the diphenyl ether sulfonamide series bound to the active site of caspase-1 was obtained.
