• Biomolecules & Therapeutics
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• 제29권4호
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• pp.410-418
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• 2021

Helicobacter pylori causes chronic gastritis through cag pathogenicity island (cagPAI), vacuolating cytotoxin A (VacA), lipopolysaccharides (LPS), and flagellin as pathogen-related molecular patterns (PAMPs), which, in combination with the pattern recognition receptors (PRRs) of host cells promotes the expression and secretion of inflammation-causing cytokines and activates innate immune responses such as inflammasomes. To identify useful compounds against H. pylori-associated gastric disorders, the effect of chalcone derivatives to activate the nucleotide-binding oligomerization domain (NOD)-like receptor family, pyrin domain-containing 3 (NLRP3) inflammasome was examined in an H. pylori-infected human monocytic THP-1 cell line in this study. Among the five synthetic structurally-related chalcone derivatives examined, 2'-hydroxy-4',6'-dimethoxychalcone (8) and 2'-hydroxy-3,4,5-trimethoxychalcone (12) strongly blocked the NLRP3 inflammasome in H. pylori-infected THP-1 cells. At 10 μM, these compounds inhibited the production of active IL-1β, IL-18, and caspase-1, and apoptosis-associated speck-like protein containing a caspase recruitment domain (ASC) oligomerization, but did not affect the expression levels of NLRP3, ASC, and pro-caspase-1. The interruption of NLRP3 inflammasome activation by these compounds was found to be mediated via the inhibition of the interleukin-1 receptor-associated kinase 4 (IRAK4)/IκBα/NF-κB signaling pathway. These compounds also inhibited caspase-4 production associated with non-canonical NLRP3 inflammasome activation. These results show for the first time that certain chalcones could interrupt the activation of the NLRP3 inflammasome in H. pylori-infected THP-1 cells. Therefore, these chalcones may be helpful in alleviating H. pylori-related inflammatory disorders including chronic gastritis.

• Bulletin of the Korean Chemical Society
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• 제26권11호
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• pp.1677-1681
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• 2005

Aldol condensation of 2-acetylthiophene, 2-acetylpyrrole and 2-acetylpyridine with different aromatic aldehydes were carried out in water in heterogeneous phases in the presence of cetyltrimethylammonium bromide as cationic surfactant at room temperature. All the reactions occur in a short time with excellent yields of steroselective hetarylpropanones in water as environmental friendly solvent.

• Bulletin of the Korean Chemical Society
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• 제32권11호
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• pp.3887-3892
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• 2011

An efficient synthesis of 1,5-Benzothiazepines via Michael addition of corresponding (E)-1-(2-hydroxyphenyl)-3-(4-(phenylthio)phenyl)prop-2-en-1-one is described under ultrasound irradiation. A series of novel 2-((E)-2,3-dihydro-2-(4-(phenylthio)phenyl)benzo[b][1,4]thiazepin-4-yl)phenol derivatives was confirmed on the basis of $^1H$ NMR, Mass, IR spectral data and Elemental analysis. The synthesized compounds were evaluated for their antimicrobial activities. Most of the compounds were found to be comparable potent than the reference standard drugs. Utilization of ultrasound irradiation, simple reaction conditions, isolation, and purification makes this manipulation very interesting from an economic and environmental perspective.

• Bulletin of the Korean Chemical Society
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• 제29권6호
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• pp.1205-1210
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• 2008

A new and efficient synthetic approach is reported for biologically interesting prenylated chalcones, 4'-Omethylxanthohumol (3), xanthohumol E (4), and sericone (5) from 2,4,6-trihydroxyacetophenone. The strategies involve the introduction of a prenyl group onto an aryl ring, benzopyran formation, and basecatalyzed aldol reactions.

• 대한화학회지
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• 제52권3호
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• pp.257-265
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• 2008

새로운 다섯개의 tetrahydroquinazolines 의 합성과 구조 결정 및 생물학적 평가는 보고 되었다. 최초에 준비된 cyclohexanones는 목표분자를 얻기 위한 synthon으로 사용되어졌다. 이들은 치환된 벤즈알데히드와 결합되어졌고, 얻어진 chalcone은 구아니딘 염산염으로 처리했다. 모든 분자들은 인간세포에 무독하며 상당한 항균성을 보여줬다.

• Natural Product Sciences
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• 제10권5호
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• pp.207-210
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• 2004

Three chalcones and a stilbenoid have been isolated from the stem bark of Lindera erythrocarpa. They were elucidated as 2'-hydroxy-3',4',5',6'- tetramethoxychalcone, 2',4'-dihydroxy-3',6'-dimethoxy chalcone, 2',4',5',6'- tetrahydroxy-3'-methoxychalcone, and 5,6-dihydroxy-2,3,4-trimethoxystilbene. Chemical structures were elucidated on the basis of MS, $^1H,\;^{13}C$ and 2D-NMR spectroscopic data. This is the first report on the isolation of these compounds from the L. erythrocarpa.

• Journal of Photoscience
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• 제8권1호
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• pp.9-12
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• 2001

The photoisomerization behavior of benzylideneacetophenones, known as chalcones, was studied. We synthesized the chalcone derivatives that have ether groups at 4 and 4＇ positions. Due to the electron donating ability of the ether oxygen, the bond order of the single bond between two phenyl ring of the chalcone strengthened, which eventually increased the rotational barrier of the single bond. The rotational barrier of the single bond is about 20-22 kcal/mole. Thermal recovery of this process took about 1 min. The UV-visible spectra of these chromophores exhibit two characteristic absorption peaks at 276 nm and 340 nm. The relative intensity of the peaks varies depending on the alkyl chain length of the substituent. Photo-irradiation with the 365 nm light monotonously decreases the 340 nm peak. However, the photo-irradiation with 254 nm light induce two competing processes and produced rather complicated absorption profile.

• 한국정보디스플레이학회:학술대회논문집
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• 한국정보디스플레이학회 2002년도 International Meeting on Information Display
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• pp.479-482
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• 2002

Benzylideneacetophenones are known as chalcones[1]. The chalcone has been known to be a photo-isomerizable and photo-dimerizable chromophore. The chalcone derivatives were prepared by base-catalyzed condensation of aldehydes and acetophenones, which were substituted with various alkyl chains. The synthesized chalcone was introduced into the t-BOC protected diamine through William synthesis reaction. Photocrosslinkable polyimide was prepared via one-step imidization reaction of DOCDA (5-(2,5-dioxotetrahydro furyl}-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride) and the chalcone introduced diamine using isoquinoline (5 wt%) in m-cresol. The polyimide solutions were spin-coated onto the quartz, silicone wafer and glass substrates and the obtained thin films were irradiated obliquely with linearly polarized UV light.

• Bulletin of the Korean Chemical Society
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• 제31권11호
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• pp.3180-3182
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• 2010

A simple facile 'one pot' synthesis of 2-amino-3-cyano-4,6-diarylpyridine derivatives via three component reaction of chalcone, malanonitrile and ammonium acetate under ultrasonic irradiation and grindstone technology. All the synthesized compounds have been characterized on the basis of their elemental analyses and spectral data (IR, $^1H$ NMR, $^{13}C$ NMR and Mass).

• Archives of Pharmacal Research
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• 제27권6호
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• pp.581-588
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• 2004

A series of 2, 5-dihydroxychalcones and related compounds were synthesized, and their cyto-toxicities against tumor cell lines and human umbilical venous endothelial cells (HUVEC） eval-uated. It was found that chalcones, with electron-withdrawing substituents on an A ring, exhibited significant cytotoxicities. Among the synthesized compounds, 2'-chlbro-2, 5-dihydrox-ychalcone (9） was most potent, with an $IC_{50}$ value as low as $0.31{\;}{\mu\textrm{g}}/mL$. This compound also exhibited a significant cytotoxic selectivity toward HUVEC.