Synthesis and Analgesic Activity of Some 1-Benzofurans, 1-Benzothiophenes and Indoles

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Title:Synthesis and Analgesic Activity of Some 1-Benzofurans, 1-Benzothiophenes and Indoles
Creators:
Rádl, Stanislav
Hezký, Petr
Urbánková, Jitka
Váchal, Petr
Krejčí, Ivan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 2, pp. 280-296
Uncontrolled Keywords:Analgesics, Benzothiophenes, Benzofurans, Xanthoxyline analogs, Indoles

Abstract

3-Unsubstituted 1-benzofurans <strong>1e</strong> and <strong>1f</strong>, 3-methyl-1-benzofurans <strong>1a</strong>-<strong>1d</strong>, and 3-amino-1-benzofurans <strong>2a</strong>-<strong>2l</strong>, as well as 3-amino-1-benzothiophenes <strong>3a</strong>, <strong>3b</strong> and 3-aminoindoles <strong>4a</strong>-<strong>4f</strong>, <strong>11a</strong>, and <strong>11b</strong> were prepared and tested as analgesics. The 3-amino-1-benzofurans <strong>2</strong> were prepared from the corresponding 2-hydroxybenzonitriles <strong>5</strong> and phenacyl bromides <strong>6</strong> <i>via</i> intermediates <strong>7</strong>. Similar treatment of 2-sulfanylbenzonitrile (<strong>8</strong>) provided 3-amino-1-benzothiophenes <strong>3</strong>. Appropriately substituted 2-aminobenzonitriles <strong>9</strong> then provided N-substituted 3-aminoindoles <strong>4</strong>. 1-(Ethoxycarbonyl)indoles <strong>4e</strong> and <strong>4f</strong> were successfully deprotected giving indoles <strong>11a</strong> and <strong>11b</strong>, respectively.

Title:Synthesis and Analgesic Activity of Some 1-Benzofurans, 1-Benzothiophenes and Indoles
Creators:
Rádl, Stanislav
Hezký, Petr
Urbánková, Jitka
Váchal, Petr
Krejčí, Ivan
Uncontrolled Keywords:Analgesics, Benzothiophenes, Benzofurans, Xanthoxyline analogs, Indoles
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:65
Number:2
Page Range:pp. 280-296
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000280UNSPECIFIED
ID Code:1641
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Rádl, Stanislav; Hezký, Petr; Urbánková, Jitka; Váchal, Petr; Krejčí, Ivan (2000) Synthesis and Analgesic Activity of Some 1-Benzofurans, 1-Benzothiophenes and Indoles. Collection of Czechoslovak Chemical Communications, 65 (2). pp. 280-296. ISSN 0010-0765

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