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Titolo:
Synthesis and analgesic activity of some substituted 1-benzofurans and 1-benzothiophenes
Autore:
Radl, S; Hezky, P; Konvicka, P; Krejci, I;
Indirizzi:
Res Inst Pharm & Biochem, CR-13060 Prague 3, Czech Republic Res Inst Pharm& Biochem Prague Czech Republic 3 rague 3, Czech Republic
Titolo Testata:
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
fascicolo: 7, volume: 65, anno: 2000,
pagine: 1093 - 1108
SICI:
0010-0765(200007)65:7<1093:SAAAOS>2.0.ZU;2-K
Fonte:
ISI
Lingua:
ENG
Soggetto:
DERIVATIVES; ANPIRTOLINE; AGENTS;
Keywords:
benzofurans; benzothiophenes; heterocyclizations; demethylations; alkylations; antinociceptive activity; analgesics;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
28
Recensione:
Indirizzi per estratti:
Indirizzo: Radl, S Res Inst Pharm & Biochem, Kourimska 17, CR-13060 Prague 3, Czech Republic Res Inst Pharm & Biochem Kourimska 17 Prague Czech Republic 3 lic
Citazione:
S. Radl et al., "Synthesis and analgesic activity of some substituted 1-benzofurans and 1-benzothiophenes", COLL CZECH, 65(7), 2000, pp. 1093-1108

Abstract

2-Benzoyl- and 2-(pyridylcarbonyl)-1-benzofuran-3-amines were prepared from 2-hydroxybenzonitrile and corresponding bromoethanone derivatives. 2-Benzoyl- and 2-(pyridylcarbonyl)-1-benzothiophene-3-amines were prepared analogously from 2-sulfanylbenzonitrile. 2-Benzoyl-1-benzofuran-3-amine treated with acetic anhydride or ethyl chloroformate provided the corresponding N-acetyl or N-ethoxycarbonyl derivatives. These N-activated compounds were alkylated with ethyl bromoacetate to provide ethyl N-acetyl-N-(2-benzoyl-1-benzofuran-3-yl)glycinate and ethyl N-(2-benzoyl-1-benzofuran-3-yl)-N-ethoxycarbonylglycinate, respectively. Their mild hydrolysis gave the corresponding glycine derivatives. Methylation of ethyl N-(2-benzoyl)-1-benzofuran-3-yl)carbamate gave the corresponding N-methyl carbamate, which was hydrolyzed toN-methyl-(2-benzoyl-1-benzofuran-3-yl)amine. 2-Benzoyl-7-methoxy-1-benzofuran-3-amine and 2-(4-methoxybenzoyl-1-benzofuran-3-amine were demethylated with boron tribromide to the corresponding hydroxy derivatives; their O-alkylation with ethyl bromoacetate than gave ethyl [(3-amino 2-benzoyl-1-benzofuran-7-yl)oxy]acetate and ethyl {4-[(3-amino-1-benzofuran-2-yl)carbonyl] phenoxy}acetate, respectively. The mild hydrolysis of these esters provided corresponding acids. Similarly, alkylation of the hydroxy derivatives with (dimethylamino)propyl chloride gave corresponding (dimethylamino)propoxy derivatives. 2-Hydroxybenzonitrile treated with 2-bromo-1-(2-, 3-, or 4-pyridyl)ethan-1-one provided the respective 2-(pyridylcarbonyl)-1-benzofuran-3-amine. Similar 2-(pyridylcarbonyl)-1-benzothiophene-3-amines were prepared analogously from 2-sulfanylbenzonitrile. 2-Benzoyl-3-(bromomethyl)-1-benzofuran treated with dimethylamine, 1-methylpiperazine, and sodium 1-methylpiperidine-4-thiolate gave the corresponding alkylation products. Several compounds were found to exhibit considerable analgesic activity.

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Documento generato il 12/07/20 alle ore 09:31:56