2309-48-0Relevant academic research and scientific papers
Ultrasounds-mediated 10-seconds synthesis of chalcones as potential farnesyltransferase inhibitors
Farce, Amaury,Ghinet, Alina,Homerin, Germain,Nica, Adrian Sorin,Dubois, Jo?lle
supporting information, (2020/04/10)
A broad range of chalcones and derivatives were easily and rapidly synthesized, following Claisen-Schmidt condensation of (hetero)aryl ketones and (hetero)aryl aldehydes using a ultrasound probe. A comparison was made with classical magnetic stirring experiments, and an optimization study was realized, showing lithium hydroxide to be the best basic catalyst of the studied condensations. By-products of the reactions (β-hydroxy-ketone, diketones, and cyclohexanols) were also isolated. All compounds were evaluated in vitro for their ability to inhibit human farnesyltransferase, a protein implicated in cancer and rare diseases and on the NCI-60 cancer cell lines panel. Molecules showed inhibitory activity on the target protein and cytostatic effect on different cell lines with particular activity against MCF7, breast cancer cells.
Synthesis, molecular modeling, and biological evaluation of 4-[5-aryl-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes
Yamali, Cem,Gul, Halise Inci,Ece, Abdulilah,Taslimi, Parham,Gulcin, Ilhami
, p. 854 - 866 (2017/12/13)
In this study, 4-[5-aryl-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl] benzenesulfonamides were synthesized, and inhibition effects on AChE, hCA I, and hCA II were evaluated. Ki values of the compounds toward hCA I were in the range of 24.2?±?4.6-49.8?±?12.8?nm, while they were in the range of 37.3?±?9.0-65.3?±?16.7?nm toward hCA II. Ki values of the acetazolamide were 282.1?±?19.7?nm and 103.60?±?27.6?nm toward both isoenzymes, respectively. The compounds inhibited AChE with Ki in the range of 22.7?±?10.3-109.1?±?27.0?nm, whereas the tacrine had Ki value of 66.5?±?13.8?nm. Electronic structure calculations at M06-L/6-31?+?G(d,p)//AM1 level and molecular docking studies were also performed to enlighten inhibition mechanism and to support experimental findings. Results obtained from calculations of molecular properties showed that the compounds obey drug-likeness properties. The experimental and computational findings obtained in this study might be useful in the design of novel inhibitors against hCA I, hCA II, and AChE.
Hetero-Diels–Alder reactions of hetaryl thiochalcones with acetylenic dienophiles
Mlostoń, Grzegorz,Grzelak, Paulina,Heimgartner, Heinz
, p. 1 - 10 (2017/01/17)
Hetaryl-substituted thiochalcones react with acetylenic mono- and diesters in the THF solution in the presence of LiClO4 at 65°C to give, after 24 h, 4H-thiopyran carboxylates and dicarboxylates, respectively, in moderate to good yields. The same reactions were performed also in the THF solution without a catalyst under microwave irradiation. In that case, the reaction time was reduced to three minutes and, in most cases, an improvement in the yield of the [4+2]-cycloadduct was observed. The reactions with methyl propiolate occurred regioselectively and the 3-carboxylates were formed exclusively.
Practical and Efficient Synthesis of Polyaryl(hetaryl)-Substituted Cyclohexenones and Salicylates
Shirinian, Valerii Z.,Kavun, Alexey M.,Lvov, Andrey G.,Zavarzin, Igor V.,Krayushkin, Michail M.
, p. 1255 - 1263 (2017/03/11)
A new efficient method was developed for the synthesis of triaryl-substituted cyclohexenones and salicylates. The method is based on the Robinson annulation of readily available keto esters and chalcones, followed by the aromatization of the cyclohexenone moiety. The aromatization can be accomplished either by reaction with bromine in boiling chloroform or bromination with copper(II) bromide in ethanol followed by treatment with pyridine or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The new synthetic method was also implemented in a one-pot protocol, which in some cases resulted in higher yields of the final product compared to those obtained in the stepwise synthesis.
2,3,5 TRISUBSTITUTED PYRROLE DERIVATIVES AS TOPOISOMERASE INHIBITORS AND THERAPEUTIC USES THEREOF
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Page/Page column 25; 33, (2017/03/14)
The compounds of Formula (1) having topoisomerase inhibitory effect includes [Formula should be inserted here] wherein, R1 is selected from a group consisting of H, OR5, optionally substituted C1-C12 alkyl, haloalkyl, C2-C12alkenyl, C2-C12alkynyl, C1-C12alkyloxy, C1-C12haloalkyloxy, C2-C10 heteroalkyl, C3- C12 cycloalkyl, C3-C12cycloalkenyl, C2- C12heterocycloalkyl, C2-C2 heterocycloalkenyl, C6-C18aryl, and C1-C18heteroaryl; R2, R3 and R4 are independently selected from a group consisting of H, halogen, CN, - NO2, SH, CF3, OH, CO2H, CONH2, OCF3, optionally substituted C1-C12alkyl, optionally substituted C1-C12haloalkyl optionally substituted C2-C12alkenyl, optionally substituted C2- C12alkynyl, optionally substituted C1-C12alkyloxy, optionally substituted C1- C12haloalkyloxy, optionally substituted C2-C12heteroalkyl, optionally substituted C3- C12cycloalkyl, optionally substituted C3-C12 cycloalkenyl, optionally substituted C2-C12 heterocycloalkyl, optionally substituted C2-C12 heterocycloalkenyl, optionally substituted C6- C18aryl, and optionally substituted C1-C18heteroaryl; R5 is selected H, optionally substituted C1-C12alkyl, optionally substituted C2- C12alkenyl, optionally substituted optionally substituted C1-C12 haloalkyl, optionally substituted C3-C12cycloalkyl, optionally substituted C6- C18aryl, and optionally substituted C1- Ci18heteroaryl; or a pharmaceutically acceptable salt, N-oxide, or prodrug thereof.
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).
Synthesis and Antimicrobial Activity of Racemic 1,5-Diols: 2-(1,3-Diaryl-3-hydroxypropyl)cyclohexan-1-ol Derivatives
Gezegen, Hayreddin,Tutar, U?ur,Ceylan, Mustafa
, p. 608 - 616 (2016/08/24)
A series of novel racemic 2-(1,3-diaryl-3-hydroxypropyl)cyclohexan-1-ol derivatives were synthesized from 1,5-diketones. All the synthesized compounds were characterized by spectroscopic methods. The antibacterial activities of obtained chiral 1,5-diols were investigated against four Gram-positive and three Gram-negative bacteria by determining of minimum inhibitory concentrations (MICs) in vitro. Compounds 3b, 3c, and 3d were found to be active against Enterococcus faecalis and Escherichia coli. In addition, compound 3j were found to be moderately active against all tested bacterial strains.
Metal-free allylation of electron-rich heteroaryl boronic acids with allylic alcohols
Li, Xue-Dong,Xie, Li-Jun,Kong, De-Long,Liu, Li,Cheng, Liang
, p. 1873 - 1880 (2017/03/10)
A convenient and regioselective cross-coupling of heteroaryl boronic acids with allylic alcohols under catalyst-free reaction conditions is described. The developed procedure is simple, works under external oxidant- and metal-free conditions, and proves to be very general with an unprecedented ortho-selectivity. This approach represents one of the very few examples of ortho-functionalization of boronic acids.
