“…Preparation of hydrochloride salts of the resulting bases was necessary to prevent
decomposition and improve their solubility in polar solvents. These compounds were
previously synthesized conventionally [15]. Microwave assistance resulted in reduced reaction time (from
16 to 20 h to 24 min); however, we did not notice any meaningful increase in product
yield.…”
Section: Resultsmentioning
confidence: 68%
“…1). Acids
1–6 were prepared as described elsewhere
[15] and converted to their ammonium
salts to improve solubility in polar solvents. Acids 1–4 and 6 were esterified with
methanol to protect the carboxyl group against O -alkylation.Fig.…”
Section: Resultsmentioning
confidence: 99%
“…They did not inhibit the growth of
any of the microorganisms (MIC > 30 μmol/cm 3 ). Methyl
esters 1a–7a of the acids [15] were not tested for antimicrobial
activity.…”
Section: Resultsmentioning
confidence: 99%
“…Encouraged by
this, and in continuation of our research, we designed the synthesis of a series of
benzofurancarboxylates bearing O -aminoethyl
substituents and assayed their antimicrobial activity. In this study we report their
microwave-assisted preparation and discuss the advantages of this technique compared
with synthesis under conventional conditions, described elsewhere [15]. The X-ray structure of 2-( N , N -diethylamino)ethyl
6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylate ( 1c ) is presented, with inter and intramolecular interactions in the
solid state.…”
A series of derivatives of 2 and 3-benzofurancarboxylates were synthesized
under microwave-assisted conditions. Their in-vitro antimicrobial properties were
assessed. Inhibition by the compounds of the growth of antibiotic-susceptible
standards and clinically isolated strains of Gram-positive and Gram-negative
bacteria, yeasts, and a human fungal pathogen was moderate to significant. Methyl
5-bromo-7-[2-(N,N-diethylamino)ethoxy]-6-methoxy-2-benzofurancarboxylate
hydrochloride was identified as the most active compound (MIC
3–12 × 10−3 μmol/cm3
against Gram-positive bacteria; MIC
9.4 × 10−2 μmol/cm3
against Candida and Aspergillus brasiliensis). The molecular and crystal structures of
2-(N,N-diethylamino)ethyl
6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylate were established by
single-crystal X-ray diffraction.Graphical Abstract.
“…Preparation of hydrochloride salts of the resulting bases was necessary to prevent
decomposition and improve their solubility in polar solvents. These compounds were
previously synthesized conventionally [15]. Microwave assistance resulted in reduced reaction time (from
16 to 20 h to 24 min); however, we did not notice any meaningful increase in product
yield.…”
Section: Resultsmentioning
confidence: 68%
“…1). Acids
1–6 were prepared as described elsewhere
[15] and converted to their ammonium
salts to improve solubility in polar solvents. Acids 1–4 and 6 were esterified with
methanol to protect the carboxyl group against O -alkylation.Fig.…”
Section: Resultsmentioning
confidence: 99%
“…They did not inhibit the growth of
any of the microorganisms (MIC > 30 μmol/cm 3 ). Methyl
esters 1a–7a of the acids [15] were not tested for antimicrobial
activity.…”
Section: Resultsmentioning
confidence: 99%
“…Encouraged by
this, and in continuation of our research, we designed the synthesis of a series of
benzofurancarboxylates bearing O -aminoethyl
substituents and assayed their antimicrobial activity. In this study we report their
microwave-assisted preparation and discuss the advantages of this technique compared
with synthesis under conventional conditions, described elsewhere [15]. The X-ray structure of 2-( N , N -diethylamino)ethyl
6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylate ( 1c ) is presented, with inter and intramolecular interactions in the
solid state.…”
A series of derivatives of 2 and 3-benzofurancarboxylates were synthesized
under microwave-assisted conditions. Their in-vitro antimicrobial properties were
assessed. Inhibition by the compounds of the growth of antibiotic-susceptible
standards and clinically isolated strains of Gram-positive and Gram-negative
bacteria, yeasts, and a human fungal pathogen was moderate to significant. Methyl
5-bromo-7-[2-(N,N-diethylamino)ethoxy]-6-methoxy-2-benzofurancarboxylate
hydrochloride was identified as the most active compound (MIC
3–12 × 10−3 μmol/cm3
against Gram-positive bacteria; MIC
9.4 × 10−2 μmol/cm3
against Candida and Aspergillus brasiliensis). The molecular and crystal structures of
2-(N,N-diethylamino)ethyl
6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylate were established by
single-crystal X-ray diffraction.Graphical Abstract.
“…As it can be seen from Table 2, a variety of o-hydroxy aryl ketones 4a-e reacted smoothly with aniline, 2-nitroaniline, pyridin-2-amine or pyridin-3-amine to generate the corresponding target products in good yields with excellent selectivity. According to the experimental results, the o-hydroxy aryl ketone containing an ethyl or n-propyl group gave higher yields of the desired benzofuran products than that of the o-hydroxy aryl ketone with a methyl group (Table 2, entries 2-4, 6-8, [9][10][11][12][13][14]. Such a comparison of the data indicated that the larger steric hindrance in alkyl substitution group of o-hydroxy aryl ketone unit contributed to significantly higher substrate conversion rate.…”
A facile and effective method has been developed for the synthesis of a novel series of benzofuran derivatives via N-acylation, O-alkylation and intramolecular condensation reactions, starting from readily available substituted o-hydroxy aryl ketone, and chloroacetyl arylamides. This metal-free transition process is characterized by mild reaction conditions, atom economy, short reaction time and a high yield with a decreased amount of by-products.
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.; HEJCHMAN*, E.; WOLSKA, I.; Farmaco 60 (2005) 6-7, 519-527; Chair Lab. Org. Chem., Fac. Pharm., Med. Acad., PL-02-097 Warszawa, Pol.; Eng.) -H. Hoennerscheid 46-101
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