Synthesis and Evaluation of 3-Methyl-4-oxo-6-phenyl-4,5,6,7-tetrahydrobenzofuran-2-carboxylic Acid Ethyl Ester Derivatives as Potent Antitumor Agents

Hayakawa, Ichiro; Shioya, Rieko; Agatsuma, Toshinori; Sugano, Yuichi

doi:10.1248/cpb.53.638

Cited by 25 publications

(9 citation statements)

References 4 publications

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“…The yellow crystals obtained during heating were filtered off and crystallized from ethanol to give compound 2 as yellow crystals. Yield (4), 187 (4), 91 (100), 80 (7), 65 (15). Anal.…”

Section: Methodsmentioning

confidence: 99%

“…Generally, furochromones are known to have anti‐inflammatory and analgesic , antitumor , and antimicrobial activities . Benzofurans showed a wide range of biological activities including aromatase inhibitory effect , anti‐HIV , anticancer potency , antimicrobial , antitumor and antiviral , analgesic, and anticonvulsant activities . One of the most important categories of khellin is 6‐formylkhellin (4,9‐dimethoxy‐5‐oxo‐5 H ‐furo[3,2‐ g ]chromene‐6‐carboxaldehyde) ; the unique position of aldehydic group in 6‐formylkhellin is typically similar to 3‐formylchromone.…”

Section: Introductionmentioning

confidence: 99%

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Chemical Reactivity of 4,9‐Dimethoxy‐5‐oxo‐5H‐furo[3,2‐g]chromene‐6‐Carboxaldehyde Toward Some Nucleophilic Reagents

El‐Gohary

Ibrahim

El‐Sawy

et al. 2016

Journal of Heterocyclic Chem

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The chemical reactivity of 4,9‐dimethoxy‐5‐oxo‐5H‐furo[3,2‐g]chromene‐6‐carboxaldehyde (6‐formylkhellin) (1) was studied toward a diversity of nitrogen nucleophilic reagents. Reaction of carboxaldehyde 1 with some primary amines and heterocyclic amines afforded the corresponding Schiff bases. Also, the reactivity of carboxaldehyde 1 was studied toward some hydrazine derivatives, namely 7‐chloro‐4‐hydrazinoquinoline, 3‐hydrazino‐5,6‐diphenyl‐1,2,4‐triazine, N4‐phenylthiosemicarbazide, and S‐benzyldithiocarbazate. 6‐Formylkhellin (1) underwent ring transformation upon treatment with hydroxylamine hydrochloride producing 5‐hydroxy‐4,9‐dimethoxy‐7‐oxo‐7H‐furo[3,2‐g]chromene‐6‐carbonitrile (22). Some pyrimidine, [1,2,4]triazolo[4,3‐a]pyrimidine, tetrazolo[1,5‐a]pyrimidine, and diazepine derivatives linked benzofuran were efficiently synthesized. Reaction of carboxaldehyde 1 with a variety of 1,4‐binucleophiles produced furochromone‐fused benzodiazepine, pyridotriazepine, benzoxazepine, and benzothiazepine derivatives. Some unsymmetrical thiocarbohydrazones were also synthesized. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data.

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“…The yellow crystals obtained during heating were filtered off and crystallized from ethanol to give compound 2 as yellow crystals. Yield (4), 187 (4), 91 (100), 80 (7), 65 (15). Anal.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chemical Reactivity of 4,9‐Dimethoxy‐5‐oxo‐5H‐furo[3,2‐g]chromene‐6‐Carboxaldehyde Toward Some Nucleophilic Reagents

El‐Gohary

Ibrahim

El‐Sawy

et al. 2016

Journal of Heterocyclic Chem

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“…The core structure of 4‐keto‐4,5,6,7‐tetrahydrobenzofuran is an important intermediate in the preparation of a wide range of synthetic compounds with diverse biological applications . Indeed, Hayakawa demonstrated recently that tetrahydrobenzofurans represent an interesting alternative scaffold to benzofuran, for the generation of new heterocyclic libraries . Interestingly, higher oxidized analogs of tetrahydrobenzofurans such as Stemofuran B are isolated from natural plants .…”

Section: Introductionmentioning

confidence: 99%

Water‐Based Synthesis of Novel 6, 7‐Dihydrobenzofuran‐4 (5H) ‐Ones

Khoeiniha

Olyaei

Saraei

2016

Journal of Heterocyclic Chem

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A simple, efficient, and high yielding one‐pot protocol for the synthesis of 4‐keto‐4,5,6,7‐tetrahydrobenzofurans has been developed by three‐component coupling reaction of dimedone, phenylglyoxal monohydrate, and heteroaryl amines in eco‐friendly solvent water under reflux conditions. The protocol avoids the use of catalysts, toxic solvents, tedious work‐up procedures, and chromatographic separation. The reaction proceeds at fast rates within 45 min and provides access to a variety of fused‐ring furans in high to excellent yields.

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“…Tetrahydrobenzofuran derivatives are important heterocycles in natural products, 1 pharmaceuticals 2 and diverse synthetic intermediates 3 because of their various pharmacological activities including antioxidant, 4 antitumor, 5 anti-ulcer, 6 photoreagents 2 and so on. The bioactive bis(heterocyclyl)alkanes constitute valuable building blocks used as protective groups, 7 photochromic materials 8 and drugs 9 in synthetic, industrial and medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

Facile and eco-friendly synthesis of bis(tetrahydrobenzofuran-2-yl)alkane derivatives catalyzed by H2S04.SiO2 under solvent-free conditions

Jin¹,

Wang²,

Cao³

et al. 2014

Arkivoc

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A series of bis(2-tetrahydrobenzofuranyl)alkanes were efficiently prepared in high yields (69-98%) from 3-methyl-6,7-dihydrobenzofuran-4(5H)-ones and aldehydes under solvent-free conditions. The eco-friendly condensation reaction was smoothly catalyzed by H 2 SO 4 •SiO 2 (30% w/w) in three minutes at 90 ºC, and the catalyst could also be recycled up to nine successive cycles without significant loss in catalytic activity.

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Synthesis and Evaluation of 3-Methyl-4-oxo-6-phenyl-4,5,6,7-tetrahydrobenzofuran-2-carboxylic Acid Ethyl Ester Derivatives as Potent Antitumor Agents

Cited by 25 publications

References 4 publications

Chemical Reactivity of 4,9‐Dimethoxy‐5‐oxo‐5H‐furo[3,2‐g]chromene‐6‐Carboxaldehyde Toward Some Nucleophilic Reagents

Chemical Reactivity of 4,9‐Dimethoxy‐5‐oxo‐5H‐furo[3,2‐g]chromene‐6‐Carboxaldehyde Toward Some Nucleophilic Reagents

Water‐Based Synthesis of Novel 6, 7‐Dihydrobenzofuran‐4 (5H) ‐Ones

Facile and eco-friendly synthesis of bis(tetrahydrobenzofuran-2-yl)alkane derivatives catalyzed by H2S04.SiO2 under solvent-free conditions

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