35225-79-7Relevant academic research and scientific papers
Incorporation of nanosized ZnWO4 and Fe3O4 on graphitic carbon nitride to fabricate a novel, highly active magnetically recoverable catalyst in Claisen–Schmidt condensation
Paul, Arijita,Devi, Meghali,Dhar, Siddhartha Sankar
, (2020)
Herein we outline a facile and viable approach for successful anchoring of ZnWO4 and Fe3O4 nanoparticles on graphitic carbon nitride (g-C3N4) through ultrasonication and microwave irradiation. The as-synthesised nanocomposite, g-C3N4–Fe3O4–ZnWO4, was characterised using Fourier transmission infrared spectroscopy, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, transmission electron microscopy, vibrating-sample magnetometry, and X-ray photoelectron spectroscopy techniques. The nanocomposite exhibited appreciable catalytic performance in the Claisen–Schmidt condensation reaction between benzaldehyde and acetone producing dibenzalacetone with excellent yields. The as-prepared catalyst demonstrated excellent magnetically recyclable property for seven successive runs. The presence of g-C3N4 in the nanocomposite g-C3N4–Fe3O4–ZnWO4 played a significant role in promoting the catalytic activity due to its inherent basic nature and efficient grafting of the substrates onto the g-C3N4 sheets.
Synthesis, characterization, DFT and molecular docking studies for novel 1,5-diphenylpenta-1,4-dien-3-one O-benzyl oximes
Erdogan, Taner
, p. 2243 - 2255 (2019)
The main objectives of this study are: (a) to synthesize novel 1,5-diphenylpenta-1,4-dien-3-one O-benzyl oximes in an efficient way, (b) to investigate the synthesized molecules computationally via DFT calculations, (c) to compare computationally obtained data with experimental results and (d) to perform molecular docking calculations for the newly synthesized compounds and heat shock protein HSP90A N-terminal domain to determine the binding affinities of the investigated molecules and to reveal possible receptor–ligand interactions. In the first part of the study, syntheses and characterizations of the investigated compounds have been carried out. In this part, the target compounds have been synthesized and characterized successively. In the synthesis of target compounds from corresponding oximes, ultrasound has been used alternatively and results showed that the usage of ultrasound considerably increases the reaction rate and the efficiency. In the second part, detailed density functional theory calculations have been performed on the investigated compounds with the use of Becke, three-parameter, Lee–Yang–Parr hybrid functional and various basis sets. In this part, geometry optimizations, frequency analyses, NMR spectral analyses, frontier molecular orbital calculations, and molecular electrostatic potential map calculations have been performed. In NMR spectral analyses, both continuous set of gauge transformations (CSGT) and gauge-independent atomic orbital (GIAO) methods have been used and the obtained results with the use of various basis sets have been compared. Results showed that in NMR calculations, GIAO method is more successful than CSGT method and can provide satisfactory results even with small basis sets. In the third part of the study, molecular docking calculations have been performed on the investigated compounds and HSP90A N-terminal domain. Results showed that investigated molecules show a good binding affinity for HSP90A N-terminal domain. The binding affinities were found to be in the range of ? 8.7 to ? 10.1?kcal/mol.
Synthesis, characterization and evaluation of topical antiinflammatory activity of dimethyl 4-oxo-2,6-diphenylcyclohexane-1,1-dicarboxylate
Al Ugla, Mazin Nadhim Mousa
, p. 2366 - 2368 (2013)
An attempt was made to synthesize a topical preparation of an active compound that has a potent antiinflammatory activity. Dimethyl 4- oxo-2,6-diphenylcyclohexane-1,1-dicarboxylate (II) was prepared by aldol condensation of benzaldehyde and acetone followed by Michael addition of dimethyl malonate. The optimum concentration of the compound was determined by comparing the antiinflammatory effect of ointment preparations at different concentrations. The antiinflammatory effects were studied by using carrageenan-induced paw edema method in rat and xylene induced rat ear edema. Good effect was observed with ointment containing 4 % and 5 % of the compound II concentration. The results showed that the drug had an obvious antiinflammatory effect as an external preparation and the activity is comparable to that of the standard ointment.
Application of monocarbonyl curcumin compound in preparation of medicine for preventing and treating periodontitis
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Paragraph 0024-0026; 0028, (2021/06/22)
The invention belongs to the technical field of medicines, and particularly relates to application of a specific monocarbonyl curcumin analogue in preparation of a medicine for preventing and treating periodontitis. Experiments prove that the monocarbonyl curcumin analogues not only can play a better anti-oxidation protection role by activating an Nrf2/HO-1 signal channel, but also can play an anti-inflammatory role by inhibiting release of inflammatory factors TNF alpha and IL1-beta, so that the monocarbonyl curcumin analogues have a remarkable prevention and treatment effect on rat periodontitis, have good potential value and significance for prevention and treatment of periodontitis, and have a good research and development prospect.
Monofunctional curcumin analogues: evaluation of green and safe developers of latent fingerprints
Pacheco, Bruna S.,Da Silva, Caroline C.,Da Rosa, Bruno N.,Mariotti, Kristiane C.,Nicolodi, Caroline,Poletti, Taís,Segatto, Natália V.,Collares, Tiago,Seixas, Fabiana K.,Paniz, Oscar,Carre?o, Neftali Lenin Vilarreal,Pereira, Claudio M. P.
, p. 3119 - 3129 (2021/02/26)
Fingerprint development is one of the most useful techniques in forensic investigation. The powder method is widely used, as it consists of a non-destructive testing. However, some of the powders commonly used are toxic and dangerous to human health. In this sense, monofunctional analogues of curcumin (3a–e) are proposed as novel coloring powders for the development of latent fingerprints. Granulometric and scanning electron microscopy analysis were performed for a better understanding of the interaction between developers and substrates. The best results for the development of fingerprints were obtained with compound (1E,4E)-1,5-di-p-tolylpenta-1,4-dien-3-one (3b). Development with this compound was specific and allowed detection both from male and female donors. Also, in an in vitro experiment, compound 3b presented low cytotoxicity in a mammalian cell line. Based on that, a novel alternative for latent fingerprint developers was proposed.
Antibacterial activity of a new monocarbonyl analog of curcumin MAC 4 is associated with divisome disruption
Polaquini, Carlos R.,Marques, Beatriz C.,Ayusso, Gabriela M.,Mor?o, Luana G.,Sardi, Janaína C.O.,Campos, Débora L.,Silva, Isabel C.,Cavalca, Lúcia B.,Scheffers, Dirk-Jan,Rosalen, Pedro L.,Pavan, Fernando R.,Ferreira, Henrique,Regasini, Luis O.
, (2021/02/22)
Curcumin (CUR) is a symmetrical dicarbonyl compound with antibacterial activity. On the other hand, pharmacokinetic and chemical stability limitations hinder its therapeutic application. Monocarbonyl analogs of curcumin (MACs) have been shown to overcome these barriers. We synthesized and investigated the antibacterial activity of a series of unsymmetrical MACs derived from acetone against Mycobacterium tuberculosis and Gram-negative and Gram-positive species. Phenolic MACs 4, 6 and 8 showed a broad spectrum and potent activity, mainly against M. tuberculosis, Acinetobacter baumannii and methicillin-resistant Staphylococcus aureus (MRSA), with MIC (minimum inhibitory concentration) values ranging from 0.9 to 15.6 μg/mL. The investigation regarding toxicity on human lung cells (MRC-5 and A549 lines) revealed MAC 4 was more selective than MACs 6 and 8, with SI (selectivity index) values ranging from 5.4 to 15.6. In addition, MAC 4 did not demonstrate genotoxic effects on A549 cells and it was more stable than CUR in phosphate buffer (pH 7.4) for 24 h at 37 °C. Fluorescence and phase contrast microscopies indicated that MAC 4 has the ability to disrupt the divisome of Bacillus subtilis without damaging its cytoplasmic membrane. However, biochemical investigations demonstrated that MAC 4 did not affect the GTPase activity of B. subtilis FtsZ, which is the main constituent of the bacterial divisome. These results corroborated that MAC 4 is a promising antitubercular and antibacterial agent.
Bu4NHSO4-Catalyzed Direct N-Allylation of Pyrazole and its Derivatives with Allylic Alcohols in Water: A Metal-Free, Recyclable and Sustainable System
Zhuang, Hongfeng,Lu, Nan,Ji, Na,Han, Feng,Miao, Chengxia
supporting information, p. 5461 - 5472 (2021/09/29)
Allylic amines are valuable and functional building blocks. Direct N-allylation of pyrazole and its derivatives as an atom economic strategy to provide allylic amines has been achieved only using commercial Bu4NHSO4 as the metal-free catalyst and water as the solvent without any additives. 11–93% isolated yields were obtained for the N-allylation of pyrazole and its derivatives with allylic alcohols. Bu4NHSO4 could be reused for six times by simple extraction nearly without loss of catalytic activity and was also suitable for a gram-scale production. The reaction of allylic ether and pyrazole did not occur to give the desired product indicated that allylic ether was not the active intermediate in the pathway. Density functional theory (DFT) calculations reveal that there are hydrogen bonding effects among substrates, solvent and catalyst, especially the one formed between allylic alcohol and H2O. Control experiments in different protic solvents further demonstrate the intermolecular hydrogen bonding of allylic alcohol and water. (Figure presented.).
Stereoselective synthesis, spectral characterization, docking and biological screening of coumarin derivatives
Afzal, Zakia,Nadeem, Humaira,Rashid, Naghmana
, p. 330 - 341 (2021/07/19)
The compounds being synthesized in present research are chiral in nature so for getting enantiopure compounds, stereoselective synthesis was carried out by organocatalysis. The importance of enantiopure compounds can not be overstated because the living systems are chiral in nature and response of enantiomers can be very different in living systems. The organocatalysed synthesis was accumplished using 4-hydroxycoumarin and variously substituted dibenzylideneacetones as reactants and the organocatalyst being used was 9-amino-9-deoxyepiquinine. The range of enantioselectivity achieved was 24-95%. The synthesized compounds were characterized by UV, IR, 1H NMR, 13C NMR, EIMS, UVCD, VCD and Chiral HPLC. The major focus of this research was to develop anticoagulant compounds and therefore the molecular docking studies were carried out with crystal structure of vitamin k epoxide reductase (3kp9) and then screened for in-vitro anticoagulant activity by using warfarin as positive control. Out of six synthesized compounds, four compounds (1,2,5,6) have shown greater binding affinity with 3kp9 than warfarin. In in-vitro anticoagulant studies, all compounds showed improved IC50 values than warfarin. Besides anticoagulant activity, antimocrobial activities were also carried out with six different strains of bacteria and fungi. Compound (5) showed 79% inhibition against Bacillus subtillis and 62 % inhibition against Staphylococcus aureus.
Synthesis of Ketones by C?H Functionalization of Aldehydes with Boronic Acids under Transition-Metal-Free Conditions
Roscales, Silvia,Csáky, Aurelio G.
supporting information, p. 8728 - 8732 (2021/03/16)
A method for the synthesis of ketones from aldehydes and boronic acids via a transition-metal-free C?H functionalization reaction is reported. The method employs nitrosobenzene as a reagent to drive the simultaneous activation of the boronic acid as a boronate and the activation of the C?H bond of the aldehyde as an iminium species that triggers the key C?C bond-forming step via an intramolecular migration from boron to carbon. These findings constitute a practical, scalable, and operationally straightforward method for the synthesis of ketones.
Supramolecular polymeric aggregation behavior and its impact on catalytic properties of imidazolium based hydrophilic ionic liquids
Muhammad, Shoaib,Javed, Muhammad Naveed,Ali, Firdous Imran,Bari, Ahmed,Hashmi, Imran Ali
, (2020/01/21)
Ionic Liquids (ILs) self-assemble to form supramolecular polymeric clusters/aggregates. The aggregation behavior of ILs influences its activity in the organic synthesis. However, the precise role of ILs in organic reactions is still unknown. It is, therefore, important to comprehend the supramolecular polymeric aggregation behavior of ILs. We are exploring the supramolecular polymeric aggregation behavior of ILs using Electrospray Ionization Mass Spectrometry (ESI-MS). We have synthesized four hydrophilic ILs (1–4) and investigated their aggregation behavior and its impact on catalytic activity in Carbon-Carbon bond formation (Knoevenagel and Claisen-Schmidt condensation). Here, we show that the aggregation behavior of ILs depends on the type and nature of cation and anion. ESI-MS (?ve) spectra reveals two different type of aggregation i.e. [CnAn+1]? & [A2 + H+]?. We have found that catalytic activity increases with increased [CnAn+1]? supramolecular aggregation. Consequently, highest yield of products obtained in ILs which show decreased anion-anion aggregation [A2 + H+]? abundance in ESI-MS. We anticipate our results to be a starting point for the establishment of desired ILs for organic synthesis.
