Novel chromene derivatives as TNF-α inhibitors

Cheng, Jie‐Fei; Ishikawa, Akira; Ono, Yoshio; Arrhenius, Thomas; Nadzan, Alex M.

doi:10.1016/j.bmcl.2003.08.025

Cited by 117 publications

(46 citation statements)

References 21 publications

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“…To a solution of 6-chloro-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid (2) (2.20 g, 7.5 mmol) and 5-allylsulfanyl- [1,3,4]thiadiazol-2-ylamine (1) (1.30 g, 7.5 mmol), in dry acetonitrile (100 mL), TBTU (4.81 g, 15 mmol) and Et 3 N (3.1 mL, 22.5 mmol) were added. The mixture was stirred for 24 h at 40 °C with TLC monitoring using ethyl acetate: ethylene dichloride (1:1) as eluent.…”

Section: Methodsmentioning

confidence: 99%

“…trifluoromethyl-2H-chromene-3-carboxylic acid (5-allylsulfanyl- [1,3,4]thiadiazol-2-yl)-amide, and it was fully characterized.…”

Section: M830 (Page 2)mentioning

confidence: 99%

“…Many compounds containing chromene ring moiety display broad spectrum of biological activity [1][2][3][4]. 2H-Chromenes have gained much attention because of various biological activities such as antiviral, anti-tumor, anti-bacterial, fungicidal, antiflamatory, antioxidative and activator of potassium channels effects [5][6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

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6-Chloro-2-hydroxy-2-trifluoromethyl-2H-chromene-3-carboxylic acid (5-allylsulfanyl-[1,3,4]thiadiazol-2-yl)-amide

Wang

Chen

Yang

et al. 2014

Molbank

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Section: Methodsmentioning

confidence: 99%

“…trifluoromethyl-2H-chromene-3-carboxylic acid (5-allylsulfanyl- [1,3,4]thiadiazol-2-yl)-amide, and it was fully characterized.…”

Section: M830 (Page 2)mentioning

confidence: 99%

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6-Chloro-2-hydroxy-2-trifluoromethyl-2H-chromene-3-carboxylic acid (5-allylsulfanyl-[1,3,4]thiadiazol-2-yl)-amide

Wang

Chen

Yang

et al. 2014

Molbank

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“…Coumarin derivatives containing benzopyrones structure [5,6] are important heterocyclic organic compounds used in different applications such as the food industry [7], pharmaceuticals [8], as precursors for organic compounds [9], cosmetics [10], optical brighteners [11], and anticoagulants [12,13]. Coumarins have also merged into various biological purposes such as antibacterial [14] anticancer [15], antimicrobial [16], antioxidant [17][18][19] and antiinhibitor [20,21].…”

Section: Introductionmentioning

confidence: 99%

Catalytic Activity of Sulfated and Phosphated Catalysts towards the Synthesis of Substituted Coumarin

et al. 2018

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New modified acidic catalysts were prepared from the treatment of silica, titania and silica prepared from hydrolyzed tetraethyl orthosilicate (TEOS) with sulfuric and phosphoric acid. The sulfated and phosphated silica synthesized from TEOS were calcined at 450 and 650 • C. These catalysts were characterized by X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FTIR), transmission electron microscope (TEM), and scanning electron microscope (SEM). The surface areas, total pore volume, and mean pore radius of the acidic catalysts were investigated, while the pore size distribution was determined by the Barrett, Joyner and Halenda (BJH) method. The catalytic activity of the sulfated and phosphated silica and/or titania were examined with the Pechmann condensation reaction, in which different phenols reacted with ethyl acetoacetate as a neat reaction to obtain the corresponding coumarin derivatives. The results indicated that the treatment of the catalysts with sulfuric or phosphoric acid led to a decrease in the phases' crystallinity to a certain degree. The morphology and the structure of the acidified catalysts were examined and their particle size was calculated. Furthermore, the amount of the used catalysts played a vital role in controlling the formation of the products as well as their performance was manipulated by the number and nature of the active acidic sites on their surfaces. The obtained results suggested that the highest catalytic conversion of the reaction was attained at 20 wt % of the catalyst and no further increase in the product yield was detected when the amount of catalyst exceeded this value. Meanwhile the phenol molecules were a key feature in obtaining the final product.

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“…Chromenes derivatives significant heterocycles that are known to have multiple biological activities 1 for instance, antibacterial, 2 antitumor, 3 sex pheromonal, 4 antimicrobial, 5 TNF-a inhibitory, 6 anticancer, 7 antifungal, 8 estrogenic, 9 antiviral 10 and anti-HIV. 11 Such compounds have also been applied in pigments, and insecticides 12 and therefore, a number of methods and catalysts have been reported for the synthesis of chromene derivatives such as, a [1-(n-butyl)-3-methylimidazolium hydroxide ( 31 Many of the above methods have their own advantages.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of ethyl-3-amino-1-aryl-1H-benzo[f]chromeme-2-carboxylate derivatives promoted by DMAP

Zeidanlu¹,

Sheikh²,

Lari³

et al. 2017

10.5267/j.ccl

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An efficient route, convenient and environmentally friendly procedure for the synthesis chromenes derivatives have been developed via a three-component coupling and one-pot reactions of various aromatic aldehyde with malononitrile or ethyl cyanoacetate and phenols in the presence N,N-dimethylpyridin-4-amine (DMAP) in reflux conditions. In simple reaction conditions, the use of DMAP is explored as an easy workup and a green catalyst for the onepot three-component synthesis ethyl 3-amino-1-aryl-1H-benzo[f]chromene-2-carboxylate derivatives.

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Novel chromene derivatives as TNF-α inhibitors

Cited by 117 publications

References 21 publications

6-Chloro-2-hydroxy-2-trifluoromethyl-2H-chromene-3-carboxylic acid (5-allylsulfanyl-[1,3,4]thiadiazol-2-yl)-amide

6-Chloro-2-hydroxy-2-trifluoromethyl-2H-chromene-3-carboxylic acid (5-allylsulfanyl-[1,3,4]thiadiazol-2-yl)-amide

Catalytic Activity of Sulfated and Phosphated Catalysts towards the Synthesis of Substituted Coumarin

Synthesis of ethyl-3-amino-1-aryl-1H-benzo[f]chromeme-2-carboxylate derivatives promoted by DMAP

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