Synthesis and Antinociceptive Activity of Some 3-Chlorophenyl- and 6-Chloropyridin-2-yl Derivatives

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Title:Synthesis and Antinociceptive Activity of Some 3-Chlorophenyl- and 6-Chloropyridin-2-yl Derivatives
Creators:
Rádl, Stanislav
Hafner, Wieland
Hezký, Petr
Krejčí, Ivan
Proška, Jan
Hájíček, Josef
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 2, pp. 377-388
Uncontrolled Keywords:Analgesics, Piperidines, Pyridines, Anpirtoline, Analgesic activity, (Pyridin-2-yl)piperidines, Phenylpiperidines

Abstract

Derivatives of 2-chloro-6-(4-hydroxy-1-methylpiperidin-4-yl)pyridine (<strong>2b</strong>) were prepared and tested as analgesics. 2-Chloro-6-lithiopyridine treated with quinuclidin-3-one, 1-methylpyrrolidin-3-one, 2-(dimethylaminomethyl)cyclohexanone, and ethyl 1-methylpiperidin-4-ylcarboxylate provided the corresponding alcohols <strong>5</strong>, <strong>6</strong>, <strong>13a</strong>, and 6-chloro-2-pyridyl 1-methylpiperidin-4-yl ketone (<strong>9</strong>). The ketone was reduced with sodium borohydride or treated with methylmagnesium chloride or phenyllithium to provide the corresponding alcohols <strong>11</strong>, <strong>12a</strong> and <strong>12b</strong>, respectively. 1-[4-(6-Chloro-2-pyridyl)1-methylpiperidin-4-yl]-1-methylethanol (<strong>4b</strong>) was prepared from 2-chloro-6-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)pyridine (<strong>14b</strong>) by treatment with butyllithium and acetone followed by reduction of intermediate <strong>15b</strong> with sodium cyanoborohydride. <p>

Title:Synthesis and Antinociceptive Activity of Some 3-Chlorophenyl- and 6-Chloropyridin-2-yl Derivatives
Creators:
Rádl, Stanislav
Hafner, Wieland
Hezký, Petr
Krejčí, Ivan
Proška, Jan
Hájíček, Josef
Uncontrolled Keywords:Analgesics, Piperidines, Pyridines, Anpirtoline, Analgesic activity, (Pyridin-2-yl)piperidines, Phenylpiperidines
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. 377-388
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990377UNSPECIFIED
ID Code:1483
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; Hájíček, Josef (1999) Synthesis and Antinociceptive Activity of Some 3-Chlorophenyl- and 6-Chloropyridin-2-yl Derivatives. Collection of Czechoslovak Chemical Communications, 64 (2). pp. 377-388. ISSN 0010-0765

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