3988-76-9Relevant academic research and scientific papers
Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols
Chan, Chieh-Kai,Tsai, Yu-Lin,Chang, Meng-Yang
, p. 3368 - 3376 (2017/05/22)
Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols provides chalcones and benzyl styrenes. The use of various metal triflates is investigated herein for facile and efficient redox transformation. A plausible mechanism has been proposed.
Ultrasound-assisted rapid and efficient one-pot synthesis of furanyl spirooxindolo and spiroquinoxalinopyrrolizidines by 1,3-dipolar cycloaddition: a green protocol
Nishtala, Venkata Bharat,Nanubolu, Jagadeesh Babu,Basavoju, Srinivas
, p. 1365 - 1381 (2017/02/15)
Efficient synthesis of novel spirooxindolo and spiroquinoxalinopyrrolizidine derivatives was expediently accomplished with regioselectivity via one-pot, three-component 1,3-dipolar cycloaddition using ultrasonication. Chalcones derived from both heteroaryl methyl ketones and furfural were used as dipolarophiles in these reactions. The synthesized compounds were analyzed by 1H and 13C nuclear magnetic resonance (NMR), mass spectrometry, and elemental (CHN) analysis. Single-crystal X-ray diffraction studies of one of the compounds (11d) proved the structure and regiochemistry of the cycloaddition. The ultrasound methodology is clearly advantageous, and the desired products were obtained in moderate to good yield in shorter reaction time compared with conventional heating and fusion methods.
Aluminum chloride-catalyzed C-alkylation of pyrrole and indole with chalcone and bis-chalcone derivatives
Gürdere, Meliha Burcu,?zbek, Oguz,Ceylan, Mustafa
, p. 322 - 331 (2016/03/23)
The AlCl3-catalyzed alkylation of pyrrole (2) with chalcone (1a-i) at a ratio of 8:1 in the presence of 10 mol% AlCl3 gave the solely 2-alkyl pyrroles (3a-i) at room temperature for 12 in good yields. The same reaction was performed with pyrrole (2) and chalcone at a ratio of 1:3 in CH3CN at rt for 3 h to achieve 2,5-dialkyl pyrroles (4a-f). In addition, the reaction of the pyrrole (2) and indole (7) on 1,4-phenylene bis-chalcones (5a-g) at the ratio of 8:1 at rt for 24 h gave the double-addition products 6a-g and 8a-g in good yields, respectively. The structure of the products was confirmed by 1H and 13C NMR spectroscopy and elemental analysis.
Triethylamin-mediated addition of 2-aminoethanethiol hydrochloride to chalcones: Synthesis of 3-(2-aminoethylthio)-1-(aryl)-3-(thiophen-2-yl) propan-1-ones and 5,7-diaryl-2,3,6, 7-tetrahydro-1,4-thiazepines
Gürdere, Meliha Burcu,Eme?, Ali Cemal,Aslan, Osman Nuri,Budak, Yakup,Ceylan, Mustafa
, p. 536 - 545 (2016/05/02)
The triethylamin-mediated addition of 2-aminoethanethiol hydrochloride to chalcone analogs was investigated. This addition, bearing a 2-thienyl group at the 3-position, gave the only addition adduct at room temperature in 3 h, whereas the chalcones bearing the 2-furyl group at the 1-position gave an addition-cyclization product (1, 4-thiazepine) in the same conditions. The effect of the groups to the reaction was investigated by changing the 1- and 3-position groups. The chalcones bearing the 2-thienyl group at the 1-position and the others afforded the mixture of products in different ratio at rt for 0.5-24 h. Moreover, the addition-cyclization products (1,4-thiazepine) were obtained under reflux conditions in 36 h. The structures of the synthesized compounds were elucidated by 1H NMR, 13C NMR, infrared, and elemental analysis.
Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation, and ulcerogenic liability of new 1,3,5-triarylpyrazoline derivatives possessing a methanesulfonyl pharmacophore
Abdellatif, Khaled R. A.,Fadaly, Wael A. A.,Azouz, Amany A.
, p. 1 - 7 (2016/10/11)
A new series of 1,3,5-triarylpyrazolines 13a–l was synthesized and all prepared compounds were evaluated for their in vitro COX-1/COX-2 inhibitory activity and in vivo anti-inflammatory activity. All test compounds were more selective for the COX-2 isozyme and showed good in vivo anti-inflammatory activity. Compound 13h was the most COX-2 selective compound (COX-2 selectivity index (SI)=10.23) and the most potent anti-inflammatory derivative (ED50-60.1μmol/kg) in comparison with celecoxib (COX-2 SI=9.29 and ED50=81.4μmol/kg). All screened compounds were less ulcerogenic (ulcer indexes (UI)=0.33–1.33) than aspirin (UI=2.33) and comparable to celecoxib (UI=0.33).
4-Fluoro-3′,4′,5′-trimethoxychalcone as a new anti-invasive agent. From discovery to initial validation in an in vivo metastasis model
Roman, Bart I.,De Ryck, Tine,Patronov, Atanas,Slavov, Svetoslav H.,Vanhoecke, Barbara W.A.,Katritzky, Alan R.,Bracke, Marc E.,Stevens, Christian V.
, p. 627 - 639 (2015/08/03)
Invasion and metastasis are responsible for 90% of cancer-related mortality. Herein, we report on our quest for novel, clinically relevant inhibitors of local invasion, based on a broad screen of natural products in a phenotypic assay. Starting from micromolar chalcone hits, a predictive QSAR model for diaryl propenones was developed, and synthetic analogues with a 100-fold increase in potency were obtained. Two nanomolar hits underwent efficacy validation and eADMET profiling; one compound was shown to increase the survival time in an artificial metastasis model in nude mice. Although the molecular mechanism(s) by which these substances mediate efficacy remain(s) unrevealed, we were able to eliminate the major targets commonly associated with antineoplastic chalcones.
Synthesis and In Vitro Antifungal Evaluation of 1,3,5-Trisubstituted-2-Pyrazoline Derivatives
Deng, Hui,Yu, Zhi-Yi,Shi, Guan-Ying,Chen, Ming-Jing,Tao, Ke,Hou, Tai-Ping
experimental part, p. 279 - 289 (2012/05/20)
Pyrazolines, the well-known five-membered nitrogen-containing heterocyclic compounds, have received considerable interests in the fields of medicinal and agricultural chemistry because of their broad spectrum of biological activities. To discover more pot
Atom-efficient, solvent-free, green synthesis of chalcones by grinding
Rateb, Nora M.,Zohdi, Hussein F.
experimental part, p. 2789 - 2794 (2009/12/06)
An improved Claisen-Schmidt condensation reaction of methyl ketones and aromatic aldehydes can be achieved by grinding at room temperature in the absence of solvents. This process is simple, efficient, economical, and environmentally benign compared to classical reactions.
Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives
Oezdemir, Zuhal,Kandilci, H. Burak,Guemuesel, Buelent,Calis, Uensal,Bilgin, A. Altan
, p. 373 - 379 (2008/02/01)
Twelve 1-phenyl-, 1-thiocarbamoyl- and 1-N-substituted thiocarbamoyl-3-(2-furyl)-5-phenyl/(2-furyl)-2-pyrazoline derivatives were synthesized. The chemical structures of the compounds were proved by IR, 1H NMR, Mass spectrometric data and micro
NOVEL PROPENONE DERIVATIVES CONTAINING AROMATIC RINGS, A MAUFACTURING PROCESS THEREOF AND A COMPOSITION CONTAINING THE SAME USING AS AN ANTIINFLAMMATORY AGENT
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Page/Page column 17, (2010/02/15)
The present invention is related to novel propenone derivatives containing aromatic ring, a manufacturing process thereof and a composition containing the same using as an anti? inflammatory agent. The compound of the present invention show potent anti-inflammatory activity confirmed by various experiments for example, the inhibition test of COX and 5-LOX enzyme activity, the inhibition test of LTC reproduction and NO production, MTT assay test, the inhibition test on the iNOS and COX-2 protein expression and PGE reproduction using RAW 264.7 macrophage etc. Accordingly, present compounds can be useful in treating and preventing various inflammatory.
