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- Title
Synthesis of some 6-alkylureido-4-aryl-2(1H)-pyridones: further transformations and pharmacological activity.
- Authors
Raev, Lyubomir Dimitrov; Ivanov, Ivo Christov; Astroug, Henri Angel; Agontseva, Silviya Georgieva; Frey, Wolfgang
- Abstract
The Michael addition of enaminoesters to coumarins (1) does not lead to the formation of simple adducts 3 but to the rearranged 4-aryl-2-pyridone 4a. Now, N-carbamoylation of the 6-amino-2-pyridone 4a with alkyl isocyanates and further transformation of the corresponding novel ureido-2-pyridone derivatives 6a–g into chromeno[3,4-c]pyridines 5d,g and O-acetyl derivatives 7a–g are reported. All newly synthesized compounds were characterized by means of 1H/13C NMR, MS, IR spectra and elemental analysis. The structure of the ureide 6f and of the N-cyclohexyl-O-acetyl derivative 7g were additionally confirmed by crystal structure determinations. Acute toxicity after intraperitoneal administration, blood clotting time, analgesic activity and the effects on the hexobarbital sleeping time were tested on laboratory animals (compounds 4a, 6a, 6c, 6d and 6g).
- Subjects
ACUTE toxicity testing; ANALGESICS; BLOOD coagulation disorders; CRYSTAL structure; UREIDES
- Publication
Zeitschrift für Naturforschung B: A Journal of Chemical Sciences, 2015, Vol 70, Issue 11, p797
- ISSN
0932-0776
- Publication type
Article
- DOI
10.1515/znb-2015-0066