Salicylamide inhibitors of influenza virus fusion.
Combrink KD, Gulgeze HB, Yu KL, Pearce BC, Trehan AK, Wei J, Deshpande M, Krystal M, Torri A, Luo G, Cianci C, Danetz S, Tiley L, Meanwell NA.
Structural variation of the quinolizidine heterocycle of the influenza fusion inhibitor BMY-27709 was examined by several topological dissections in order to illuminate the critical features of the ring system. This exercise resulted in the identification of a series of synthetically more accessible decahydroquinolines that retained the structural elements of BMY-27709 important for antiviral activity. The 2-methyl-cis-decahydroquinoline 6f was the most potent influenza inhibitor identified that demonstrated an EC50 of 90 ng/mL in a plaque reduction assay.