Synthesis and Ocular Effects of Imidazole Nitrolic Acids

• Published in: Journal of medicinal chemistry Vol. 48; no. 13; pp. 4231 - 4236
• Main Authors: Oresmaa, Larisa, Kotikoski, Hanna, Haukka, Matti, Salminen, Johanna, Oksala, Olli, Pohjala, Esko, Moilanen, Eeva, Vapaatalo, Heikki, Vainiotalo, Pirjo, Aulaskari, Paula
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 30.06.2005; Amer Chemical Soc
• Subjects: Animals; Aqueous Humor - drug effects; Aqueous Humor - physiology; Biological and medical sciences; Chemistry, Medicinal; Cyclic GMP - metabolism; Drug Design; Eye; Imidazoles - chemical synthesis; Imidazoles - pharmacology; Iris - drug effects; Iris - physiology; Life Sciences & Biomedicine; Medical sciences; Models, Molecular; Molecular Structure; Nitrates - metabolism; Nitrites - metabolism; Nitroglycerin - chemical synthesis; Nitroglycerin - pharmacology; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Science & Technology; Swine; EYE; MONKEY; RABBITS; CYCLIC-GMP; MECHANISM; AQUEOUS-HUMOR; OUTFLOW FACILITY; NITRIC-OXIDE DONORS; GLAUCOMA; LOWERS INTRAOCULAR-PRESSURE; Ciliary body; Imidazole derivatives; Five membered ring; Nitrogen heterocycle; Nitrites; Rabbit; Nitrates; Aqueous humor; Eye drop; Eye; Local administration; Structure activity relation; Nitrolic acid; Chemical synthesis; Ungulata; 3',5'-GMP; Lagomorpha; In vitro; Pig; In vivo; Vertebrata; Nitric oxide donor; Mammalia; Position isomer; Animal; Artiodactyla; Intraocular administration; Intraocular pressure
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm048949+

Novel 1-R-imidazole-2-nitrolic acids and 1-R-imidazole-5-nitrolic acids (R:  H, Me, Bn) were synthesized from oximes by treatment with a mixture of fuming nitric acid and acetic acid. The effects of these potential nitric oxide-donating compounds were tested on ocular variables such as intraocular pressure and formation of cyclic guanosine-3,5‘-monophosphate in the incubation of porcine iris-ciliary body.