Studies on chemical modification of monensin IX. Synthesis of 26-substituted monensins and their Na+ ion transport activity.
The C-26 modified monensin derivatives, 26-O-benzoylmonensin (3), 26-O-benzylmonensin (4) and 26-phenylaminomonensin (5) were prepared from monensin (1). Na+ ion transport activity through biological membrane and antibacterial activity of 3-5 were evaluated and compared with the activities reported for a 26-phenylurethane derivative (2). Among these compounds, 5 showed the largest Na+ ion transport and antibacterial activities. In these compounds, the formation of head-to-tail hydrogen bonds was suggested to be an important factor for Na+ ion transport and antibacterial activities.
Tanaka
R
R
Faculty of Pharmaceutical Sciences, Nagoya City University, Japan.
Nagatsu
A
A
Mizukami
H
H
Ogihara
Y
Y
Sakakibara
J
J
D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D017136:Ion Transport; D008985:Monensin / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D012964:Sodium / Q000378:metabolism*; D013057:Spectrum Analysis
D000890:Anti-Infective Agents; D008985:Monensin; D012964:Sodium