Nitrogen-bound diazeniumdiolated amidines.
In contrast to amidines bearing ionizable alpha-CH bonds, which react with nitric oxide (NO) to add diazeniumdiolate groups at their alpha-carbons, benzamidine forms an N-bound diazeniumdiolate that can be further derivatized at the other amidine nitrogen and/or the terminal oxygen to form caged NO compounds as potential NO prodrugs.
Biswas
Debanjan
D
Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, Frederick, MD 21702, USA. biswasd@mail.nih.gov
Deschamps
Jeffrey R
JR
Keefer
Larry K
LK
Hrabie
Joseph A
JA
D000578:Amidines / Q000138:chemical synthesis / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D008968:Molecular Conformation; D009569:Nitric Oxide / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D011355:Prodrugs / Q000138:chemical synthesis / Q000737:chemistry
D000578:Amidines; D001391:Azo Compounds; D011355:Prodrugs; C452539:diazeniumdiolate; D009569:Nitric Oxide; D009584:Nitrogen