NO donors. Part 16: investigations on structure-activity relationships of organic mononitrates reveal 2-nitrooxyethylammoniumnitrate as a high potent vasodilator.
The vasoactive properties of 14 organic mononitrates were investigated in vitro using PGF(2alpha)-precontracted porcine pulmonary arteries. A surprisingly wide range of vasorelaxant potencies was observed (pD(2): 3.36-7.50). Activities showed to be highly sensitive to the molecular structure and the substituents at the molecular carrier of the nitrate group. A correlation between lipophilicity and vasorelaxant potency could not be recognized. 2-Nitrooxyethylammoniumnitrate (1) was found to be slightly superior to the high potency trinitrate GTN.
Koenig
Andreas
A
Lehrstuhl für Pharmazeutische/Medizinische Chemie, Institut für Pharmazie, Friedrich-Schiller-Universität Jena, Philosophenweg 14, D-07743 Jena, Germany.
Roegler
Carolin
C
Lange
Kathrin
K
Daiber
Andreas
A
Glusa
Erika
E
Lehmann
Jochen
J
D009566:Nitrates / Q000737:chemistry / Q000494:pharmacology; D020030:Nitric Oxide Donors / Q000737:chemistry* / Q000494:pharmacology*; D000644:Quaternary Ammonium Compounds / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014665:Vasodilator Agents / Q000737:chemistry* / Q000494:pharmacology*
C526166:2-nitrooxyethylammoniumnitrate; D009566:Nitrates; D020030:Nitric Oxide Donors; D000644:Quaternary Ammonium Compounds; D014665:Vasodilator Agents