Ring-modified analogues and molecular dynamics studies to probe the requirements for fungicidal activities of malayamycin A and its N-nucleoside variants.
The importance of functional group orientations and the integrity of the bicyclic perhydrofuran core of malayamycin A and two equally active N-nucleoside analogues as fungicides were investigated. Two analogues 10 and 11, representing a THP-truncated and a bicyclic aza-variant, were synthesized and found to be inactive. Molecular dynamics studies on malayamycin A and analogues were performed to highlight the importance of properly orientating the urea and methyl ether groups.
Loiseleur
Olivier
O
Syngenta, Crop Protection Research, Schwarzwaldallee 215, CH-4002 Basel, Switzerland. olivier.loiseleur@syngenta.com
Ritson
Dougal
D
Nina
Mafalda
M
Crowley
Patrick
P
Wagner
Trixie
T
Hanessian
Stephen
S
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry* / Q000494:pharmacology; D002384:Catalysis; D005659:Fungicides, Industrial / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015335:Molecular Probes; D009705:Nucleosides / Q000737:chemistry* / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization
D019086:Bridged Bicyclo Compounds, Heterocyclic; D005659:Fungicides, Industrial; D015335:Molecular Probes; D009705:Nucleosides; C493874:malayamycin A