5-phenyl-1-benzofuran-2-yl derivatives: synthesis, antimicrobial, and antioxidant activity

Aswathanarayanappa, Chandrashekar; Bheemappa, Eswarappa; Bodke, Yadav D.; Bhovi, Venkatesh K.; Ningegowda, Raghu; Shivakumar, M. C.; Peethambar, S. K.; Telkar, Sandeep

doi:10.1007/s00044-012-0017-y

Cited by 37 publications

(22 citation statements)

References 15 publications

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“…First, the reaction of one-pot Michael-O-alkylation pertaining bromination and base-mediated cyclization was employed to construct a furan ring. [26][27][28] Second, the resulting 2-acetyl furanonaphthoquinone was subjected to methylation via Grignard's reaction to form an isopropyl alcohol side chain (Chart 3). Under this strategy, lawsone (7a) was used as the starting material and was treated with an effective Michael acceptor, such as methyl vinyl ketone (8a), pen-1-en-3-one (8b), and methyl vinyl sulfone (8c) to obtain the desired furanonaphthoquinones 5a-f at a yield of 12-57%.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Evaluation and Molecular Docking of Avicequinone C Analogues as Potential Steroid 5α-Reductase Inhibitors

Karnsomwan

Netcharoensirisuk

Rungrotmongkol

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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Avicequinone C (5a), a furanonaphthoquinone isolated from the Thai mangrove Avicennia marina has been shown previously to have interesting steroid 5α-reductase type 1 inhibitory activity. In this study, a series of avicequinone C analogues containing furanonaphthoquinone with different degrees of saturation and substituents at the furan ring were synthesized. The resulting synthetic avicequinone C and analogues (5a-f) along with some related compounds including 2,5-dihydroxy-1,4-benzoquinone (6) and natural naphthoquinones such as lawsone (7a) and lapachol (7b) were evaluated for their in vitro cell viability and steroid 5α-reductase type 1 inhibitory activities using the cultured cell line of human keratinocytes (HaCaT). This cell-based bioassay was performed based on a direct detection of the enzymatic product dihydrotestosterone (2) by using a non-radioactive high performance thin layer chromatography (HPTLC) method. Among the furanonaphthoquinones in this series, 5e having a propionic substituent at furan ring possessed approximately 22-fold more potent than the original isolated compound 5a. However, the compounds without furan motif such as 6, 7a and b could not inhibit the activity of steroid 5α-reductase. Molecular docking results of the in silico three-dimensional steroid 5α-reductase type 1-reduced nicotinamide adenine dinucleotide phosphate (NADPH) binary complex was performed via AutoDock Vina and it illustrated that the furanonaphthoquinone moiety and the substituent at furan ring might play a key role as pharmacophores for the steroid 5α-reductase inhibitory activity.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Evaluation and Molecular Docking of Avicequinone C Analogues as Potential Steroid 5α-Reductase Inhibitors

Karnsomwan

Netcharoensirisuk

Rungrotmongkol

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Also, 1 H NMR spectra of 3a-c represented the characteristic triplet-quartet pattern of the ester group at the regions d 1.16-1.26 and 4.10-4.25 ppm, respectively, in addition to the parent signals of the molecules. 13 C-NMR spectrum of compound 3b displayed different signals at (d ppm): 14.9 (-CH 2 CH 3 ), 21.5, 22.0, 29.3, 30.6 (4 CH 2 , C 6 , C 7 , C 5 , C 8 ), 55.2 (pyridine-C 4 ), 55.3 (OCH 3 ), 60.0 (-CH 2 CH 3 ), 94.4 (pyridine-C 3 ), 103.3-158.1 (aromatic-C, pyridine-C) and 162.3 (C=O). Mass spectra of the compounds revealed their molecular ion peaks which were in consistent with their molecular formulae.…”

Section: Results and Discussion Chemistrymentioning

confidence: 97%

“…They exhibited, in addition to the parent protons, a new singlet signal at d 3.06-3.21 ppm representing the two methylene protons of the newly formed pyrazolone ring, and a singlet signal was recorded at d 5.98-6.10 ppm for the NH 2 group that exchanged with D 2 O. 13 C-NMR spectrum of 7b, revealed signals at 75.2 (CH 2 , pyrazolone), and 164.6, 168.8 ppm (2C=O). Mass spectra of the 7a, b were inconsistent with their chemical structures.…”

Section: Results and Discussion Chemistrymentioning

confidence: 99%

“…Also, recent studies showed that novel 1,4,5,6,7,8-hexahydroquinoline derivatives have significant cytotoxic activity against different human cancer cell lines [10][11][12]. Also, literature survey documented that various benzofuran compounds are known to possess important biological properties, including antimicrobial [13][14][15], antifungal [16], antiviral [17], anti-inflammatory [18,19], antidiabetic [20], antioxidant [21,22]. Moreover, many benzofuran derivatives have shown remarkable anticancer activity [23][24][25][26].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and in vitro cytotoxic evaluation of some novel hexahydroquinoline derivatives containing benzofuran moiety

2015

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A series of new ethyl 4-(2-(benzofuran-2-yl)-4-substituted-1,4,5,6,7,8-hexahydroquinolin-1-yl)-benzoate 3a-c was synthesized by Michael condensation of benzofuran chalcones 1a-c and cyclohexanone to give 2-(2-benzofuranyl)-4-substituted-5,6,7,8-tetrahydro-4-H -chromene 2a-c, followed by reaction of the latter with ethyl 4-aminobenzoate. Condensation of 3a-c with different amines afforded the corresponding amides 4a-e. On the other hand, upon treatment compounds 3a-c with hydrazine hydrate gave the benzohydrazide derivatives 5a-c. The reaction of compounds 5a-c with different thio/isocyanate gave the corresponding thiosemicarbazide and semicarbazide derivatives 6a-c. Meanwhile compounds 5a-c were reacted with ethyl cyanoacetate and different b-dicarbonyl compounds such as acetyl acetone, ethyl acetoacetate, and diethyl malonate to afford pyrazolyl derivatives 7a, b; 8a, b; 9a, b; and 10a-c, respectively. Moreover, 5a-c were reacted with carbon disulfide to synthesize the corresponding oxadiazolyl derivatives 11a-c, while their condensation with different aromatic aldehydes gave the corresponding Schiff bases 12a-d. Cytotoxic evaluation of some of the newly synthesized compounds against human hepatocellular carcinoma cell lines (HepG-2) revealed that the tested compounds produce promising inhibitory effect against the growth of HepG-2 cells with IC 50 values ranged from 11.9 to 19.3 lg/mL.

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“…These essential features are present in most popular anticonvulsant drugs such as phenytoin, carbamazepine, phenobarbital and ralitoline. Benzofuran derivatives have diverse pharmacological activities, like anticonvulsant (12)(13)(14)(15), antiinflammatory (13), analgesic (16), antioxidant and antimicrobial (17,18), neuroprotective (19), anticancer, cytotoxic, inhibiting of NF-κB and protein kinase (20)(21)(22). Benzofuran, a versatile heterocyclic molecule possessing a preliminary anticonvulsant property, has been selected to explore as a hydrophobic functional group for the binding site.…”

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confidence: 99%

Design, synthesis and evaluation of benzofuran-acetamide scaffold as potential anticonvulsant agent

et al. 2016

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A series of N-(2-(benzoyl/4-chlorobenzoyl)-benzofuran- 3-yl)-2-(substituted)-acetamide derivatives (4a-l, 5a-l) was synthesized in good yield. All synthesized compounds were in agreement with elemental and spectral data. The anticonvulsant activity of all synthesized compounds was assessed against the maximal electroshock induced seizures (MES) model in mice. Neurotoxicity was evaluated using the rotarod method. The majority of compounds exhibited anticonvulsant activity at a dose of 30 mg kg-1 body mass during 0.5-4 h, indicating their ability to prevent seizure spread at low doses. Relative to phenytoin, [N-(2-(4-chlorobenzoyl)benzofuran-3-yl)-2-(cyclohexyl( methyl) amino)-acetamide] (5i) and [N-(2-(4-chlorobenzoyl)benzofuran-3-yl)-2-(4-methylpiperidin-1- yl)-acetamide] (5c) demonstrated comparable relative anticonvulsant potency of 0.74 and 0.72, respectively, whereas [(N-(2-(4-chlorobenzoyl)benzofuran-3-yl)-2-(4-(furan-2-carbonyl)-piperazin-1-yl)-acetamide] (5f) exhibited the lowest relative potency of 0.16. The ALD50 of tested compounds ranged from 1.604 to 1.675 mmol kg-1 body mass. The ED50 of synthesized compounds ranged from 0.055 to 0.259 mmol kg-1 (~23.4 to 127.6 mg kg-1) body mass. The pharmacophore mapping of the examined compounds on standard drugs (phenobarbital, phenytoin, ralitolin and carbamazepine) strongly suggests that these compounds may exert their anticonvulsant activity via the same established mechanism as that of known drugs.

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5-phenyl-1-benzofuran-2-yl derivatives: synthesis, antimicrobial, and antioxidant activity

Cited by 37 publications

References 15 publications

Synthesis, Biological Evaluation and Molecular Docking of Avicequinone C Analogues as Potential Steroid 5α-Reductase Inhibitors

Synthesis, Biological Evaluation and Molecular Docking of Avicequinone C Analogues as Potential Steroid 5α-Reductase Inhibitors

Synthesis and in vitro cytotoxic evaluation of some novel hexahydroquinoline derivatives containing benzofuran moiety

Design, synthesis and evaluation of benzofuran-acetamide scaffold as potential anticonvulsant agent

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