Molecular Modification of Anpirtoline, a Non-Opioid Centrally Acting Analgesic

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Title:Molecular Modification of Anpirtoline, a Non-Opioid Centrally Acting Analgesic
Creators:
Rádl, Stanislav
Hafner, Wieland
Hezký, Petr
Krejčí, Ivan
Proška, Jan
Taimr, Jan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 2, pp. 363-376
Uncontrolled Keywords:Analgesics, 4-Phenylsulfanylpiperidines, Piperidines, Pyridines, Anpirtoline, Analgesic activity, 5-HT receptor ligands

Abstract

Molecular modification of anpirtoline (<strong>2a</strong>) is described. Several methods of preparation of 4-[(3-chlorophenyl)sulfanyl]-1-methylpiperidine (<strong>3a</strong>) and its demethylation led to the deazaanpirtoline (<strong>3c</strong>). 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 (<strong>6</strong>), 4-chloro-6-methyl-2-(piperidin-4-ylsulfanyl)pyridine (<strong>7</strong>), and 3-chloro-6-(piperidin-4-ylsulfanyl)pyridazine (<strong>8</strong>), respectively. 2-Chloro-6-(pyridin-4-ylsulfanyl)pyridine (<strong>10</strong>) and 4-[(2-chloropyridin-6-yl)sulfanyl]quinoline (<strong>11</strong>) were obtained from sodium 2-chloropyridine-6-thiolate. Homoanpirtoline analogs with methylene group inserted between the pyridine moiety and the sulfur atom (compound <strong>12b</strong>) as well as between the sulfur atom and the piperidine ring (compound <strong>13b</strong>) were also prepared. <p>

Title:Molecular Modification of Anpirtoline, a Non-Opioid Centrally Acting Analgesic
Creators:
Rádl, Stanislav
Hafner, Wieland
Hezký, Petr
Krejčí, Ivan
Proška, Jan
Taimr, Jan
Uncontrolled Keywords:Analgesics, 4-Phenylsulfanylpiperidines, Piperidines, Pyridines, Anpirtoline, Analgesic activity, 5-HT receptor ligands
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:64
Number:2
Page Range:pp. 363-376
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990363UNSPECIFIED
ID Code:1482
Item Type:Article
Deposited On:06 Feb 2009 17:09
Last Modified:06 Feb 2009 16:10

Citation

Rádl, Stanislav; Hafner, Wieland; Hezký, Petr; Krejčí, Ivan; Proška, Jan; Taimr, Jan (1999) Molecular Modification of Anpirtoline, a Non-Opioid Centrally Acting Analgesic. Collection of Czechoslovak Chemical Communications, 64 (2). pp. 363-376. ISSN 0010-0765

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