Synthesis, Characterization, and Biological Activities of New Benzofuran Derivatives (original) (raw)
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Synthesis of potent antitumor and antiviral benzofuran derivatives
Bioorganic & Medicinal Chemistry Letters, 2009
Cytotoxicity Antiviral activity HIV and HIV-1 RT inhibitory activity HCV NS3-4A protease inhibitor activity a b s t r a c t A new series of potent antitumor and antiviral benzofuran derivatives was synthesized by the reaction of the furochromone-6-carboxaldehydes 1 and 2 with different heterocyclic amines to yield the benzofuran-5-carbonyl derivatives 4-11. The synthesized compounds 1, 3-11 were tested against twelve different human cancer cell lines and all of the compounds were more potent than the comparative standards. The HIV inhibitory activity of the tested compounds 1, 3-11 showed that they have higher potency than Atevirdine. Moreover, compound 6 was significantly potent with wider therapeutic index. The HIV-1 RT inhibitory activity showed that compounds 10, 11, 3 and 4 were notably potent but with lower therapeutic index than Atevirdine. The HCV NS3-4A protease inhibitor activity of the tested compounds revealed that they have weaker potency and less therapeutic index than VX-950, although compounds 1, 4, 9 and 6, respectively exhibited significant activity.
Synthesis of New Benzofuran-2-Carboxylic Acid Derivatives
Journal of Chemistry, 2013
Novel ethyl ester and methylamide of 5-[bis(2-chloroethyl)amino]-7-methoxybenzofuran-2-carboxylic acid as well as (2-hydroxy-1,1-dimethylethyl)amides of 5-bromo- and 5,7-dichlorobenzofuran-2-carboxylic acid were synthesized and characterized.
2006
A series of pyridines, pyrimidinones, oxazinones and their derivatives were synthesized as antimicrobial agents using citrazinic acid (2,6-dihydroxyisonicotinic acid) as a starting material. α,β-Unsaturated ketones 3a-c were condensed with cyanothioacetamide in the presence of ammonium acetate to give 2-cyanopyridinethiones 4a-c, which were reacted with ethyl chloroacetate to yield the corresponding cyano esters 5a-c. The esters 5a-c were cyclized by action of sodium methoxide to aminoesters 6a-c, which were aminolyzed with ammonia to corresponding aminoamide derivatives 7a-c. Also, the esters 6a-c were hydrolyzed with NaOH to the corresponding sodium salt 8a-c, which were treated with acetic anhydride to afford 2-methyloxazinones 9a-c. The latter compounds were treated with ammonium acetate to afford 2-methylpyrimidinones 10a-c, followed by methylation with methyl iodide to yield 2,3-dimethyl-pyrimidinones 11a-c. The antimicrobial screening showed that many of these compounds have good antibacterial and antifungal activities comparable to streptomycin and fusidic acid used as reference drugs.
DNA binding, antiviral activities and cytotoxicity of new furochromone and benzofuran derivatives
Archives of Pharmacal Research, 2011
Bromination of visnagin (1) afforded 9-bromovisnagin (2) which on its alkaline hydrolysis afforded the 3-acetyl benzofuran derivative (3). The condensation of (3) with hydrazine hydrate, phenylhydrazine and/or hydroxylamine hydrochloride afforded the corresponding pyrazole derivatives (4a, b) and isoxazole derivative (4c). On the other hand, when compound 3 was condensed with some aromatic aldehydes, this yielded corresponding α, β-unsaturated keto derivatives (5a-e). Furthermore, when 1 was subjected to chlorosulfonation, the visnaginsulfonylchloride derivative 6 was afforded, which on amidation using morpholine, a sulonamido derivative (7) was obtained. Alkaline hydrolysis of the latter compound yielded 7-N-morpholinosulsamidobenzofuran (8) which was condensed with some aromatic aldehydes to yield the corresponding chalcone compounds (9a-e). Demethylation of visnagin afforded norvisnagin (10). The reaction of 10 with ethylbromoacetate in dry acetone yielded the ester benzopyran derivative (11) which reacted with hydrazine hydrate to afford the corresponding hydrazide derivative (12) and this was condensed with 3,4,5-trimethoxybenzaldehyde to give the corresponding hydrazone (13). A thaizolidinone derivative (14) was obtained by condensation of (13) with thioglycolic acid. Chloromethylation of norvisnagin afforded a 4-chloromethyl derivative (15) which reacted with different primary and secondary amines to yield the corresponding ethylamino derivative . Moreover, mannich bases (16a, b) and (17a-c) were obtained by reacting norvisnagin with different primary and secondary amines in the presence of formalin but benzoylation of (16a, b) and (17a-c) afforded 4-oxybenzoyl derivative (18a-e). The prepared compounds were tested for their interaction with DNA; bromovisnagin 2 showed the highest affinity and compounds 6, 15, 8a, > 14, > 16b, 17a, and 16a showed moderate activity in decreasing potency. Moreover, compound 2 also was the most active as antiviral agent toward HS-I virus and compounds 6, 7, 15, 14, 16a, and 18a were found to be moderately active. CD 50 of the active compounds were also measured.
European Journal of Medicinal Chemistry, 2008
The reaction of salicylaldehyde with 1-chloro-3-mesitylacetone (2) and potassium carbonate was used to prepare 1-(1-benzofuran-2-yl)-2mesitylethanone (4) for the starting reagent purposes. 1-(1-Benzofuran-2-yl)-2-mesitylethanoneoxime (5) was synthesized by the reaction of the compound (4) with hydroxylamine. New derivative of 1-(1-benzofuran-2-yl)-2-mesitylethanoneoxime (5) as 1-(1-benzofuran-2-yl)-2-mesitylethanonesemicarbazone (7) was obtained in very high yields. Alkyl substituted N-oxime ethers (8aed) were obtained by the reaction compound 5 and various halogen contained compounds. The compounds 9aed were synthesized by the reaction of the compound (5) and four different acyl chlorides. Some of the synthesized compounds were tested for antimicrobial activity against Staphylococcus aureus ATCC 6538, Escherichia coli ATCC 25922 and Candida albicans ATCC 10231. Among the synthesized compounds (E )-1-(1-benzofuran-2-yl)-2-mesitylethanone-O-benzoyloxime (9b) was found the most active derivative against S. aureus ATCC 6538 and E. coli ATCC 25922. The other compounds exhibited moderate activity against the other test microorganisms.
Egyptian Journal of Chemistry, 2019
T hIs Article deals with the stepwise synthesis and spectroscopic characterization of some new azo benzofuran derivatives, started from the diazotization of substituted aniline coupled with 2-hydroxy benzaldehyde. On reacting of the azo of 2-hydroxy benzaldehyde with p-bromo phenacyl bromide, the benzofuran (3a-g) are obtained. The structure of the new benzofuran derivatives have been characterized by using FT-IR, 1h-NMR,13C-NMR and DEPT-135 NMR. The biological activity of some new synthesized compound was obtained by vitro anti oxidant and anti microbial activity with both Staphylococcus aureus and Escherichia coli .The results showed that the new benzofurans have mild anti oxidant activity compared to the standard ascorbic acid.
Novel antiviral benzofuran-transition metal complexes
European Journal of Medicinal Chemistry, 2010
Antiviral activity HIV and HIV-1 RT inhibitory activity HCV NS3-4A protease inhibitor activity a b s t r a c t (5-(1H-benzo[d]imidazol-2-yl)-1H-pyrrol-3-yl)(6-hydroxy-4,7-dimethoxybenzofuran-5-yl)methanone (4) and 3-(6-hydroxy-4,7-dimethoxybenzofuran-5-carbonyl)-6H-pyrimido[1,6-a]pyrimidine-6,8(7H)-dione (5) were synthesized by the reaction of 4,7-dimethoxy-5-oxo-5H-furo[3,2-g]chromene-6-carbaldehyde (1) with (1H-benzo[d]imidazol-2-yl)methanamine dihydrochloride and 4-amino-2,6-dihydroxypyrimidine, respectively, via ROR in the presence of alcoholic KOH. The metal complexes 6-9 of compound 4; H 2 L 1 with (CuCl 2 , FeCl 3 , ZnCl 2 , and LaCl 3) and the metal complexes 10-13 of compound 5; H 2 L 2 with (CuCl 2 , FeCl 3 , CoCl 2 and LaCl 3) were synthesized to form 1:1 or 1:2 (metal: ligand) complexes. The HIV inhibitory activity of all new compounds was tested. The EC 50 values showed that, all of tested compounds were more potent than Atevirdine. Moreover, the benzoimidazolylpyrrole derivative 4 (EC 50 ¼ 9 Â 10 À6 mM) had higher therapeutic index than the standard. The HIV-1 RT inhibitory activity showed that all of the tested compounds showed significant potency but none of them showed higher activity than Atevirdine. The HCV NS3-4A protease inhibitor activity of the tested compounds revealed that the complex formation had great positive effect on the bioactivity, where the Fe-complex 7 was the most potent compound with higher therapeutic index than VX-950, the standard. Also, the cytotoxicity of the synthesized compounds on hepatocyte cell line, showed that Cu-complex 10 was the most potent compound with potency nearly to that of the standard.
Recent advantages in benzofurans
Journal of Pharmacognosy and Phytochemistry, 2019
Benzofuran as an important heterocyclic compound is extensively found in natural products as well as synthetic materials. Since benzofuran drivatives display a diverse array of pharmacological activities, an interest in developing new biologically active agents from benzofuran is still under consideration. This review highlights recent findings on biological activities of benzofuran derivatives as antimicrobial and antibreast cancer agents and lays emphasis on the importance of benzofurans as a major source for drug design and development.