Probing biotransformation relationships among pyridoacridines by focusing on oxygenated analogues.
The presence of the MeO-5 in the structure 5-methoxyamphimidine (5) is unusual in the light of a recent analysis of the relationships among sponge- and tunicate-derived pyridoacridines. We explore a possible biochemical pathway, from neoamphimidine (2) to 5-methoxyamphimidine (5). The results of semiempirical and ab initio calculations are presented to help understand the relationships that favor the formation of 5 versus the formation of undiscovered bis-oxygenated pyridoacridines.
Wenzel
Philip J
PJ
Department of Chemistry and Biochemistry and Institute for Marine Sciences, University of California, Santa Cruz, CA 95064, USA. phil@chemistry.ucsc.edu
Crews
Phillip
P
D000166:Acridines / Q000737:chemistry*; D000818:Animals; D001711:Biotransformation; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D011161:Porifera / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014561:Urochordata / Q000737:chemistry*
C478718:5-methoxyamphimidine; D000166:Acridines; D006576:Heterocyclic Compounds, 4 or More Rings; D011725:Pyridines; C478719:neoamphimidine; D010100:Oxygen