Synthesis and structural characterization of derivatives of 2- and 3-benzo[b]furan carboxylic acids with potential cytotoxic activity.
Derivatives of 2- and 3-benzo[b]furancarboxylic acids were prepared and evaluated for their cytotoxic potential in the National Cancer Institute, Bethesda, USA. Six compounds: 7-acetyl-6-hydroxy-3-methyl-2-benzofurancarboxylic acid (2), 6-hydroxy-7-(p-methoxycinnamoyl)-3-methyl-2-benzofurancarboxylic acid (4), 5-bromo-7-hydroxy-6-methoxy-2-benzofurancarboxylic acid methyl ester (6a), 6-acetyl-5-(O-ethyl-2'-diethylamino)-2-methyl-3-benzofurancarboxylic acid methyl ester (1f), 6-(O-ethyl-2'-diethylamino)-7-p-methoxycinnamoyl)-3-methyl-2-benzofurancarboxylic acid methyl ester hydrochloride (4b), 5-bromo-7-(O-ethyl-2'-diethylamino)-6-methoxy-2-benzofurancarboxylic acid methyl ester (6b) showed significant cytotoxic activities against human cancer cell lines. In addition the crystal structures of 7-methoxy-2-benzofurancarboxylic acid methyl ester (7a) has been solved by X-ray structure analysis of single crystals.
Kossakowski
Jerzy
J
Department of Medical Chemistry, Medical University of Warsaw, 3 Oczki Street, 02-007 Warsaw, Poland.
Ostrowska
Kinga
K
Hejchman
Elzbieta
E
Wolska
Irena
I
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001572:Benzofurans / Q000138:chemical synthesis* / Q000494:pharmacology; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray / Q000379:methods; D004305:Dose-Response Relationship, Drug; D006801:Humans; D015394:Molecular Structure
C510596:2-benzo(b)furan carboxylic acid; C510597:3-benzo(b)furan carboxylic acid; D000970:Antineoplastic Agents; D001572:Benzofurans; D002264:Carboxylic Acids