223684-89-7Relevant academic research and scientific papers
Molecular modification of anpirtoline, a non-opioid centrally acting analgesic
Radl, Stanislav,Hafner, Wieland,Hezky, Petr,Krejci, Ivan,Proska, Jan,Taimr, Jan
, p. 363 - 376 (2007/10/03)
Molecular modification of anpirtoline (2a) is described. Several methods of preparation of 4-[(3-chlorophenyl)sulfanyl]-1-methylpiperidine (3a) and its demethylation led to the deazaanpirtoline (3c). Nucleophilic substitution of piperidine-4-thiole with 2-chloro-4-nitropyridine, 2,4-dichloro-6-methylpyridine, and 3,6-dichloropyridazine led to 2-chloro-4-(piperidin-4-ylsulfanyl)pyridine (6), 4-chloro-6-methyl-2-(piperidin-4-ylsulfanyl)pyridine (7), and 3-chloro-6-(piperidin-4-ylsulfanyl)pyridazine (8), respectively. 2-Chloro-6-(pyridin-4-ylsulfanyl)-pyridine (10) and 4-[(2-chloropyridin-6-yl)sulfanyl]quinoline (11) were obtained from sodium 2-chloropyridine-6-thiolate. Homoanpirtoline analogs with methylene group inserted between the pyridine moiety and the sulfur atom (compound 12b) as well as between the sulfur atom and the piperidine ring (compound 13b) were also prepared.
Synthesis and analgesic activity of some deaza derivatives of anpirtoline
Radl, Stanislav,Hezky, Petr,Proska, Jan,Krejci, Ivan
, p. 13 - 18 (2007/10/03)
New deaza derivatives of anpirtoline have been synthesized by three different methods. Their receptor binding profiles (5-HT(1A), 5-HT(1B)) and analgesic activity (hot plate, acetic acid induced writhing) have been studied.
