13709-06-3Relevant articles and documents
The synthetic preparation of naturally-occurring aromatase inhibitors, morachalcone A, isogemichalcone B, and isogemichalcone C
Brandt, Drew R.,Pannone, Kristina M.,Romano, Joseph J.,Casillas, Eduard G.
, p. 9994 - 10002 (2013)
A convergent synthesis applicable to the preparation of oxidized prenylchalcones is reported that relies on key Claisen-Schmidt, Mitsunobu, and vinyl/benzyl Stille coupling operations. The synthetic strategy was applied towards the preparation of the natu
First total synthesis of (±)-sepicanin A
Yang, Jin Hui,Huang, Wen Qian,Luo, Jun Shan,Guo, Dong Dong,Zhang, Yu Heng,Li, Hong Jun
, p. 127 - 129 (2012)
A facile approach for the first total synthesis of naturally occurring geranylated flavanoids sepicanin A has been obtained with total yield 16% starting from 2,4,6-trihydroxyacetophenone after four steps. The key step was the protic acids (HCl or p-TsOH)
Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers
Teng, Yuou,Li, Xuzhe,Yang, Ke,Li, Xuehui,Zhang, Zijun,Wang, Luyao,Deng, Zhijie,Song, Binbin,Yan, Zhihong,Zhang, Yongmin,Lu, Kui,Yu, Peng
, p. 335 - 345 (2017)
Four ring-closed analogs of natural prenylated chalcone desmethylxanthohumol (1) and their dimers were synthesized from the commercially available 1-(2,4,6-trihydroxyphenyl)ethan-1-one in five and six linear steps, respectively. The structures of the eigh
COMBINATION TREATMENT OF BACTERIAL INFECTION
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Paragraph 0141; 0142, (2020/06/08)
The present invention resides in the discovery that combined use of kuraridin (or any one of its analogs) and epicatechin gallate (ECG) can provide heightened level of antimicrobial activity, especially for the suppression of bacteria of the Staphylococcus aureus and Staphylococcal species. Compositions, kits, and methods for the combination use are disclosed.
Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure-activity relationship
Jiang, Wen-Jun,Ishiuchi, Kan'Ichiro,Furukawa, Megumi,Takamiya, Tomoko,Kitanaka, Susumu,Iijima, Hiroshi
, p. 6922 - 6929 (2015/11/11)
To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells.
Chalcones as positive allosteric modulators of α7 nicotinic acetylcholine receptors: A new target for a privileged structure
Balsera, Beatriz,Mulet, José,Fernández-Carvajal, Asia,Torre-Martínez, Roberto De La,Ferrer-Montiel, Antonio,Hernández-Jiménez, José G.,Estévez-Herrera, Judith,Borges, Ricardo,Freitas, Andiara E.,López, Manuela G.,García-López, M. Teresa,González-Mu?iz, Rosario,Pérez De Vega, María Jesús,Valor, Luis M.,Svobodová, Lucie,Sala, Salvador,Sala, Francisco,Criado, Manuel
, p. 724 - 739 (2015/02/19)
The α7 acetylcholine nicotine receptor is a ligand-gated ion channel that is involved in cognition disorders, schizophrenia, pain and inflammation among other diseases. Therefore, the development of new agents that target this receptor has great significance. Positive allosteric modulators might be advantageous, since they facilitate receptor responses without directly interacting with the agonist binding site. Here we report the search for and further design of new positive allosteric modulators having the relatively simple chalcone structure. From the natural product isoliquiritigenin as starting point, chalcones substituted with hydroxyl groups at defined locations were identified as optimal and specific promoters of α77 nicotinic function. The most potent compound (2,4,2-2,5-2-tetrahydroxychalcone, 111) was further characterized showing its potential as neuroprotective, analgesic and cognitive enhancer, opening the way for future developments around the chalcone structure.
Synthesis and investigation of dihydroxychalcones as calpain and cathepsin inhibitors
Baek, Kyung Hye,Karki, Radha,Lee, Eung-Seok,Na, Younghwa,Kwon, Youngjoo
, p. 24 - 30 (2013/10/22)
In order to identify potential calpain and cathepsin inhibitors we prepared 12 dihydroxychalcone analogues and tested their ability to inhibit μ-calpain, m-calpain, cathepsins B and L. In the calpain inhibition test, compound 10 exhibited the most active
SMALL MOLECULE INHIBITORS OF IL-6 AND USES THEREOF
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Paragraph 00900; 00933, (2013/03/26)
In one aspect, the invention relates to substituted 2-(lH-indol-3-yl)ethanol analogs and substituted 3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole analogs, derivatives thereof, and related compounds, which are useful as inhibitors of IL-6 mediated activation of the Jak2/STAT3 pathway; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating disorders of uncontrolled cellular proliferation associated with a IL6 dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
Multidimensional optimization of promising antitumor xanthone derivatives
Azevedo, Carlos M.G.,Afonso, Carlos M.M.,Sousa, Diana,Lima, Raquel T.,Helena Vasconcelos,Pedro, Madalena,Barbosa, Jo?o,Corrêa, Arlene G.,Reis, Salette,Pinto, Madalena M.M.
, p. 2941 - 2959 (2013/07/05)
A promising antitumor xanthone derivative was optimized following a multidimensional approach that involved the synthesis of 17 analogues, the study of their lipophilicity and solubility, and the evaluation of their growth inhibitory activity on four human tumor cell lines. A new synthetic route for the hit xanthone derivative was also developed and applied for the synthesis of its analogues. Among the used cell lines, the HL-60 showed to be in general more sensitive to the compounds tested, with the most potent compound having a GI50 of 5.1 μM, lower than the hit compound. Lipophilicity was evaluated by the partition coefficient (Kp) of a solute between buffer and two membrane models, namely liposomes and micelles. The compounds showed a log Kp between 3 and 5 and the two membrane models showed a good correlation (r2 = 0.916) between each other. Studies concerning relationship between solubility and structure were developed for the hit compound and 5 of its analogues.
HETEROAROMATIC-CONTAINING COMPOUND, OPTICAL MATERIAL AND OPTICAL ELEMENT
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Page/Page column 32, (2011/07/30)
There are provided a heteroaromatic-containing compound represented by the following general formula (1), and an optical material including the heteroaromatic-containing compound. Formula 1 General Formula (1) wherein R1 and R2 are each independently a hydrogen atom or a methyl group, Ar1 is an aryl group which may have a substituent, and A is an aromatic hydrocarbon group. The R1 and R2 can be a hydrogen atom, and Ar1 can be a phenyl group.
