2005
DOI: 10.1002/chin.200546101
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Synthesis and Structural Characterization of Derivatives of 2‐ and 3‐Benzo[b]furan Carboxylic Acids with Potential Cytotoxic Activity.

Abstract: Activity. -The exemplary synthesis of the benzofurans proceeds via protection of the carboxylic group of acids (I) and subsequent reaction of the esterified products (III) with alkylamine (IV) under phase transfer catalysis conditions. Six compounds (I), (Vb), (VI) and (VII) display significant cytotoxic activities against human cancer cell lines. In addition, the molecular structure of a benzofuran derivative in solid state is analyzed by single crystal X-ray diffraction. -(KOSSAKOWSKI, J.; OSTROWSKA, K.; HEJ… Show more

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Cited by 3 publications
(5 citation statements)
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“…Compounds 7-acetyl-6-methoxy-3-methyl-2-benzofurancarboxylic acid (1a), methyl 7-acetyl-6-methoxy-3-methyl-2-benzofurancarboxylate (2a), 2b, methyl 7-acetyl-6-(O-ethyl-2Ј-diethylamino)-3-methyl-2-benzofurancarboxylate (3b), methyl 6-hydroxy-7-(p-methoxycinnamoyl)-3-methyl-2-benzofurancarboxylate (2c), methyl 6-(O-ethyl-2Ј-diethylamino)-7-(p-methoxycinnamoyl)-3-methyl-2-benzofurancarboxylate (3c), 2d, 3d, methyl 7-acetyl-6-(O-ethyl-2Ј-diethylamino)-5-methoxy-3-methyl-2-benzofurancarboxylate (3f), and methyl 6-acetyl-5-(Oethyl-2Ј-diethylamino)-2-methyl-3-benzofurancarboxylate (3g) were prepared according to previously reported procedures (Kossakowski et al, 2005). The O-ethyl-N,Ndiethylamino dervatives 3b, 3c, 3d, 3f, and 3g were converted to their hydrochlorides to improve their solubility in polar solvents.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Compounds 7-acetyl-6-methoxy-3-methyl-2-benzofurancarboxylic acid (1a), methyl 7-acetyl-6-methoxy-3-methyl-2-benzofurancarboxylate (2a), 2b, methyl 7-acetyl-6-(O-ethyl-2Ј-diethylamino)-3-methyl-2-benzofurancarboxylate (3b), methyl 6-hydroxy-7-(p-methoxycinnamoyl)-3-methyl-2-benzofurancarboxylate (2c), methyl 6-(O-ethyl-2Ј-diethylamino)-7-(p-methoxycinnamoyl)-3-methyl-2-benzofurancarboxylate (3c), 2d, 3d, methyl 7-acetyl-6-(O-ethyl-2Ј-diethylamino)-5-methoxy-3-methyl-2-benzofurancarboxylate (3f), and methyl 6-acetyl-5-(Oethyl-2Ј-diethylamino)-2-methyl-3-benzofurancarboxylate (3g) were prepared according to previously reported procedures (Kossakowski et al, 2005). The O-ethyl-N,Ndiethylamino dervatives 3b, 3c, 3d, 3f, and 3g were converted to their hydrochlorides to improve their solubility in polar solvents.…”
Section: Resultsmentioning
confidence: 99%
“…Compound was converted to 7-acetyl-6-hydroxy-3-methyl-2-benzofurancarboxylic acid (1b) by reaction with sodium hydroxide. The acid 1b was esterifed with methanol to give its methyl ester 2b (Kossakowski et al, 2005). Bromination of the compound 2b with bromine in acetic acid at ambient temperature afforded the novel benzofuran derivative 4 (Scheme 1).…”
Section: Resultsmentioning
confidence: 99%
“…The benzofuran derivatives, isolated from natural sources as well as synthetic, show cytostatic and/or antitumor activity (e.g., [1][2][3][4][5][6][7][8][9]). Therein, neolignans isolated from the Persea species are cytotoxic in vitro to the human cancer cell lines: mouth epidermoid carcinoma, lung adenocarcinoma, and colon adenocarcinoma [7].…”
Section: Introductionmentioning
confidence: 99%
“…Therein, neolignans isolated from the Persea species are cytotoxic in vitro to the human cancer cell lines: mouth epidermoid carcinoma, lung adenocarcinoma, and colon adenocarcinoma [7]. Recently, it was proved that derivatives of the 2-and 3-benzo [b]furancarboxylic acids showed also selective cytotoxicity against the human cancer cell lines [8,9]. Moreover, the compounds containing the benzo [b]furan system show antiprotozoal and/or antifungal activity [10][11][12][13], e.g., amiodarone, a drug used as an antiarrhythmic agent, possess significant antifungal potential [14][15][16][17][18][19].…”
Section: Introductionmentioning
confidence: 99%
“…Prompted by these reports, and in continuation of our research in the field of synthesis of new biologically active benzo [b]furans (Kossakowski et al, 2005, Kossakowski andOstrowska, 2006), we have prepared 13 new dihydrobenzofuran derivatives.…”
Section: Introductionmentioning
confidence: 99%