2960-55-6Relevant academic research and scientific papers
Mechanochemical Syntheses of N-Containing Heterocycles with TosMIC
Bolm, Carsten,Molitor, Claude,Rissanen, Kari,Schumacher, Christian,Smid, Sabrina,Truong, Khai-Nghi
, p. 14213 - 14222 (2021/09/07)
A mechanochemical van Leusen pyrrole synthesis with a base leads to 3,4-disubstitued pyrroles in moderate to excellent yields. The developed protocol is compatible with a range of electron-withdrawing groups and can also be applied to the synthesis of oxazoles. Attempts to mechanochemically convert the resulting pyrroles into porphyrins proved to be difficult.
Synthesis, characterization and structure–activity relationship of non-linear optical response of chalcone derivatives with in silico insights
Rai, Prashant,Chettri, Prajal,Kar, Swayamsiddha,Nagar, Malhar Anupam,Srivastava, Shailesh,Golakoti, Nageswara Rao
supporting information, p. 2603 - 2615 (2021/02/01)
Fifteen chalcone derivatives having D–A–D, D–A–A and A–A–D architectures have been synthesized by Claisen–Schmidt condensation reaction and characterized by UV–Vis, IR, 1H-NMR, 13C-NMR and Mass spectrometry. In order to unambiguously establish the structure–activity relationship for the non-linear optical activity of these compounds, for the first time to our knowledge, we use the femtosecond degenerate four wave mixing (DFWM) technique to quantify and compare the third-order non-linear optical (NLO) activity of all the 15 compounds, under identical conditions. The second harmonics generation (SHG) efficiencies for all the compounds have also been evaluated using the Kurtz-Perry powder method. Among the compounds that we have synthesized here, the ones with A–A–D architecture show the highest NLO activity. Our results show that the NLO activity of a compound with A–A–D architecture can be further enhanced by incorporating a substituent with strong electron withdrawing ability on ring A and strong electron donating substituent on ring B. The results of the in silico studies that we have carried out correlate well with our experimental findings. The compounds (E)-3-(4-(dimethylamino)phenyl)-1-(4-nitrophenyl)prop-2-en-1-one with the compound code (4-N(CH3)2–4′-NO2) and (E)-3-(4-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one with the compound code (4-MeO-4′-NO2) show the highest NLO activity among the compounds we have reported here. Graphical abstract: [Figure not available: see fulltext.]
Promising Non-cytotoxic Monosubstituted Chalcones to Target Monoamine Oxidase-B
Iacovino, Luca G.,Pinzi, Luca,Facchetti, Giorgio,Bortolini, Beatrice,Christodoulou, Michael S.,Binda, Claudia,Rastelli, Giulio,Rimoldi, Isabella,Passarella, Daniele,Di Paolo, Maria Luisa,Dalla Via, Lisa
supporting information, p. 1151 - 1158 (2021/06/30)
A library of monosubstituted chalcones (1-17) bearing electron-donating and electron-withdrawing groups on both aromatic rings were selected. The cell viability on human tumor cell lines was evaluated first. The compounds unable to induce detectable cytotoxicity (1, 13, and 14) were tested using the monoamine oxidase (MAO) activity assay. Interestingly, they inhibit MAO-B, acting as competitive inhibitors, with 13 and 14 showing the best profiles. In particular, 13 exhibited a potency higher than that of safinamide, taken as a reference. Docking studies and crystallographic analysis showed that in human MAO-B 13 binds with the halogen-substituted aromatic ring in the entrance cavity, similar to safinamide, whereas 14 is accommodated in the opposite way. The main conclusion of this cell biology, biochemistry, and structural study is to highlights 13 as a chalcone derivative that is worth consideration for the development of novel MAO-B-selective inhibitors for the treatment of neurodegenerative diseases.
Synthesis and characterization of 1,3,5-triarylpyrazol-4-ols and 3,5-diarylisoxazol-4-ols from chalcones and theoretical studies of the stability of pyrazol-4-ol toward acid dehydration
Cipagauta Esquivel, Edna Carolina,Rufino, Virgínia Camila,Trindade Nogueira, Matheus Henrique,Carbonaro Souza, Ana Carolina,Pliego Júnior, Josefredo Rodriguez,Valle, Marcelo Siqueira
, (2019/12/23)
The synthesis of diverse pyrazol-4-ol and isoxazole-4-ol heterocycles involving only 3 reaction steps is reported in this study. However, the synthesis of carboxamide pyrazol-4-ol has failed in the conditions used in the synthesis, acid methanol solution. The carboxamide pyrazol-4-ol decomposes via dehydration, forming the respective pyrazol. Theoretical calculations were used to elucidate the dehydration reaction. We have found a mechanism for acid-catalyzed dehydration that can explain the experimental observations. The calculated free energy profile for acid-catalyzed dehydration of the carboxamide pyrazol-4-ol and phenylpyrazole-4-ol point out that the latter is more stable in relation dehydration, with a dehydration rate 100 times smaller in acid methanol solution.
COMPOUNDS AND METHODS FOR TREATING OR PREVENTING HEART FAILURE
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Page/Page column 104; 146-147, (2020/07/25)
The present invention relates to the discovery of novel compounds that can be used to treat and/or prevent heart failure in a subject. In certain embodiments, the compounds of the invention are sulfide: quinone oxidoreductase (SQOR) inhibitors. In other e
Antiproliferative effects of chalcones on T cell acute lymphoblastic leukemia-derived cells: Role of PKCβ
Corsini, Emanuela,Facchetti, Giorgio,Esposito, Sara,Maddalon, Ambra,Rimoldi, Isabella,Christodoulou, Michael S.
, (2020/05/16)
In this study, a series of 20 chalcone derivatives was synthesized, and their antiproliferative activity was tested against the human T cell acute lymphoblastic leukemia-derived cell line, CCRF-CEM. On the basis of the structural features of the most active compounds, a new library of chalcone derivatives, according to the structure–activity relationship design, was synthesized, and their antiproliferative activity was tested against the same cancer cell line. Furthermore, four of these derivatives (compounds 3, 4, 8, 28), based on lower IC50 values (between 6.1 and 8.9 μM), were selected for further investigation regarding the modulation of the protein expression of RACK1 (receptor for activated C kinase), protein kinase C (PKC)α and PKCβ, and their action on the cell cycle level. The cell cycle analysis indicated a block in the G0/G1 phase for all four compounds, with a statistically significant decrease in the percentage of cells in the S phase, with no indication of apoptosis (sub-G0/G1 phase). Compounds 4 and 8 showed a statistically significant reduction in the expression of PKCα and an increase in PKCβ, which together with the demonstration of an antiproliferative role of PKCβ, as assessed by treating cells with a selective PKCβ activator, indicated that the observed antiproliferative effect is likely to be mediated through PKCβ induction.
Gold-catalyzed partial hydrogenation of activated alkynes mediated by triphenylphosphine
Cocoletzi-Xochitiotzi, Ana Patricia,Hernández-Hernández, Miguel,Medina-Mercado, Ignacio,Jiménez-Martínez, Williams De Jesús,Mastranzo, Virginia Maricela,Porcel, Susana
, p. 2379 - 2386 (2020/08/19)
Gold(I) can exhibit a cooperative effect with triphenylphosphine, accelerating the triphenylphosphine-mediated partial hydrogenation of activated alkynes. In this protocol, 3-arylpropiolates are selectively reduced to the Z -isomer when the aryl ring bears an electron-donor substituent, whereas 3-arylpropynones are reduced to the E-isomers.
Synthesis and characterization of co-doped fly ash catalyst for chalcone synthesis
Ghoshir,Kande,Muley,Gambhire
, p. 2165 - 2172 (2019/09/03)
A series of solid base fly ash hybrid materials were synthesized by doping alkali, alkaline earth metals with nitrogen, separately using co-precipitation process, combined with surfactant incorporating method. The catalysts were characterized by X-ray diffraction, scanning electron microscopy, transmission electron microscopy, X-ray photoelectron spectroscopy and photoluminescence spectroscopy. Results revealed that the co-doped hybrid materials are highly stable with particle size in the range of 40-60 nm. The surface basicity of fly ash was upraised by increased hydroxyl content by doping with alkali, alkaline earth metals with nitrogen. The basicity of hybrid material was measured by liquid phase, solvent free, single step condensation of 4-chlorobenzaldehyde and acetophenone giving higher conversion rate and selectivity of desired product chalcone. This conversion showed that the fly ash based hybrid material has sufficient basic site, responsible for the catalytic activity.
One-Pot Catalytic Enantioselective Synthesis of 2-Pyrazolines
Thomson, Connor J.,Barber, David M.,Dixon, Darren J.
supporting information, p. 2469 - 2473 (2019/02/01)
A scalable, one-pot, enantioselective catalytic synthesis of 2-pyrazolines from beta-substituted enones and hydrazines is described. Pivoting on a two-stage catalytic Michael addition/condensation strategy, the use of an aldehyde to generate a suitable hydrazone derivative of the hydrazine was found to be key for curtailing background reactivity and tuning the catalyst-controlled enantioselectivity. The new synthetic method is easy to perform, uses a new and readily prepared cinchona-derived bifunctional catalyst, is broad in scope, and tolerates a range of functionalities with high enantioselectivity (up to >99:1 e.r.). The significant scalability of this methodology was demonstrated with the synthesis of more than 80 grams of a pyrazoline product with 89 % catalyst recovery.
Studies of NMR Chemical Shifts of Chalcone Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices
Jeong, Eun Jeong,Lee, In-Sook Han
, p. 668 - 673 (2019/07/12)
A series of the chalcone derivatives of the five-membered monoheterocyclic compounds, (E)-1-aryl-3-heteroarylpropen-1-ones, were prepared by aldol condensation of the corresponding aldehydes of thiophene, pyrrole, and furan with m- and p-substituted acetophenones. Similar condensation of the acetyl compounds of the heterocycles with m- and p-substituted benzaldehydes gave another series of the chalcone derivatives, (E)-1-heteroaryl-3-arylpropen-1-ones. The 13C chemical shift values (δC) of the chalcone derivatives were determined in order to find if they correlated with the Hammett σ values. A good correlation, especially for the β-C for both series, was found for the 13C chemical shift values (δC) of the chalcone derivatives with the Hammett σ values. The chemical shift values of the β-C of the heterocyclic compounds were plotted against those of the benzene derivatives. The resulting slopes were found to be close to the values of the aromaticity indices.
